# Organic Chemistry/Overview of Functional Groups

## Introduction

The number of known organic compounds is quite large. In fact, there are
many times more organic compounds known than all the other (inorganic)
compounds discovered so far, about 7 million organic compounds in total.
Fortunately, organic chemicals consist of a relatively few similar
parts, combined in different ways, that allow us to predict how a
compound we have never seen before may react, by comparing how other
molecules containing the same types of parts are known to react.

These parts of organic molecules are called **functional groups**. The
identification of functional groups and the ability to predict
reactivity based on functional group properties is one of the
cornerstones of organic chemistry.

Functional groups are **specific atoms, ions, or groups of atoms**
having consistent properties. A functional group makes up part of a
larger molecule.

For example, **-OH**, the hydroxyl group that characterizes alcohols, is
an oxygen with a hydrogen attached. It could be found on any number of
different molecules.

Just as elements have distinctive properties, functional groups have
**characteristic chemistries**. An **-OH** group on one molecule will
tend to react similarly, although perhaps not identically, to an **-OH**
on another molecule.

**Organic reactions usually take place at the functional group**, so
learning about the reactivities of functional groups will prepare you to
understand many other things about organic chemistry.

## Memorizing Functional Groups

Don\'t assume that you can simply skim over the functional groups and
move on. As you proceed through the text, the writing will be in terms
of functional groups. It will be assumed that the student is familiar
with most of the ones in the tables below. It\'s simply impossible to
discuss chemistry without knowing the \"lingo\". It\'s like trying to
learn French without first learning the meaning of some of the words.

One of the easiest ways to learn functional groups is by making flash
cards. Get a pack of index cards and write the name of the functional
group on one side, and draw its chemical representation on the other.

For now, a list of the most important ones you should know is provided
here. Your initial set of cards should include, at the very least:
Alkene, Alkyne, Alkyl halide (or Haloalkane), Alcohol, Aldehyde, Ketone,
Carboxylic Acid, Acyl Chloride (or Acid Chloride), Ester, Ether, Amine,
Sulfide, and Thiol. After you\'ve learned all these, add a couple more
cards and learn those. Then add a few more and learn those. Every
functional group below is eventually discussed at one point or another
in the book. But the above list will give you what you need to continue
on.

And don\'t just look at the cards. Say and write the names and draw the
structures. To test yourself, try going through your cards and looking
at the names and then drawing their structure on a sheet of paper. Then
try going through and looking at the structures and naming them. Writing
is a good technique to help you memorize, because it is more active than
simply reading. Once you have the minimal list above memorized backwards
and forwards, you\'re ready to move on. But don\'t stop learning the
groups. If you choose to move on without learning the \"lingo\", then
you\'re not going to understand the language of the chapters to come.
Again, using the French analogy, it\'s like trying to ignore learning
the vocabulary and then picking up a novel in French and expecting to be
able to read it.

### Functional groups containing \...

In organic chemistry **functional
groups** are submolecular structural motifs, characterized by specific
elemental composition and connectivity, that confer reactivity upon the
molecule that contains them.

Common functional groups include:

+-------+-------+-------+-------+-------+-------+-------+-------+
| Sr    | Che   | Group | Fo    | Grap  | P     | S     | Ex    |
| No.   | mical |       | rmula | hical | refix | uffix | ample |
|       | class |       |       | Fo    |       |       |       |
|       |       |       |       | rmula |       |       |       |
+=======+=======+=======+=======+=======+=======+=======+=======+
| 1     | Acyl | Halof | RCOX  | !     | h     | -oyl  | ![A   |
|       | hal   | ormyl |       | [Acyl | alofo | h     | cetyl |
|       | ide |       |       | halid |       |       | l chl |
|       |       |       |       | e"){w |       |       | oride |
|       |       |       |       | idth= |       |       | "){wi |
|       |       |       |       | "75"} |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | A    |
|       |       |       |       |       |       |       | cetyl |
|       |       |       |       |       |       |       | chlor |
|       |       |       |       |       |       |       | ide\ |
|       |       |       |       |       |       |       | *(Eth |
|       |       |       |       |       |       |       | anoyl |
|       |       |       |       |       |       |       | chlor |
|       |       |       |       |       |       |       | ide)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 2     | Alco | Hyd   | OH    | !     | hyd   | -ol   | ![    |
|       | hol-s |       |       |  "met |
|       | y#A " |       |       | kelet |       |       | hanol |
|       | wikil |       |       | al.pn |       |       | "){wi |
|       | ink") |       |       | g "Hy |       |       | dth=" |
|       |       |       |       | droxy |       |       | 90"}\ |
|       |       |       |       | l"){w |       |       | Me   |
|       |       |       |       | idth= |       |       | thano |
|       |       |       |       | "75"} |       |       | l |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 3     |      | [     | RCHO  | !     | oxo-  | -al   | ![ace |
|       | Aldeh | Aldeh |       | [Alde |       |       | talde |
|       | yde | ink") |       | up.sv |       |       | ehyde |
|       |       |       |       | g "Al |       |       | "){wi |
|       |       |       |       | dehyd |       |       | dth=" |
|       |       |       |       | e"){w |       |       | 75"}\ |
|       |       |       |       | idth= |       |       | :A   |
|       |       |       |       | "75"} |       |       | cetal |
|       |       |       |       |       |       |       | dehyd |
|       |       |       |       |       |       |       | e\ |
|       |       |       |       |       |       |       | *     |
|       |       |       |       |       |       |       | (Etha |
|       |       |       |       |       |       |       | nal)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 4     | Alk  | [Alky | RH~n~ | ![A   | a     | -ane  | !     |
|       | ane |       | neral |       |       | ne-2D |
|       | ry/Gl |       |       | )-ske |       |       | -ster |
|       | ossar |       |       | letal |       |       | eo.sv |
|       | y#A " |       |       | .svg  |       |       | g "me |
|       | wikil |       |       | "Alky |       |       | thane |
|       | ink") |       |       | l"){w |       |       | "){wi |
|       |       |       |       | idth= |       |       | dth=" |
|       |       |       |       | "75"} |       |       | 75"}\ |
|       |       |       |       |       |       |       |      |
|       |       |       |       |       |       |       | Metha |
|       |       |       |       |       |       |       | ne |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 5     | Alk  | [Alke | R     | ![Al  | alk   | -ene  | ![eth |
|       | ene{w |       |       | "){wi |
|       | ink") | ink") |       | idth= |       |       | dth=" |
|       |       |       |       | "75"} |       |       | 75"}\ |
|       |       |       |       |       |       |       | Eth  |
|       |       |       |       |       |       |       | ylene |
|       |       |       |       |       |       |       | \ |
|       |       |       |       |       |       |       | *(Eth |
|       |       |       |       |       |       |       | ene)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 6     | Alk  | [Alky | RC    | !     | alk   | -yne  | !     |
|       | yne{wi |       |       | lene" |
|       | ink") | ink") |       | dth=" |       |       | ){wid |
|       |       |       |       | 100"} |       |       | th="1 |
|       |       |       |       |       |       |       | 00"}\ |
|       |       |       |       |       |       |       | [     |
|       |       |       |       |       |       |       | Acety |
|       |       |       |       |       |       |       | lene] |
|       |       |       |       |       |       |       | (w:Ac |
|       |       |       |       |       |       |       | etyle |
|       |       |       |       |       |       |       | ne "w |
|       |       |       |       |       |       |       | ikili |
|       |       |       |       |       |       |       | nk")\ |
|       |       |       |       |       |       |       | *(Eth |
|       |       |       |       |       |       |       | yne)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 7     | Am   | [C    | RCO   | ![Am  | ca    | -     | !     |
|       | ide-ske |       |       | e_ske |
|       | ossar | wikil |       | letal |       |       | letal |
|       | y#A " | ink") |       | .png  |       |       | .svg  |
|       | wikil |       |       | "Amid |       |       | "acet |
|       | ink") |       |       | e"){w |       |       | amide |
|       |       |       |       | idth= |       |       | "){wi |
|       |       |       |       | "75"} |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | [     |
|       |       |       |       |       |       |       | Aceta |
|       |       |       |       |       |       |       | mide] |
|       |       |       |       |       |       |       | (w:Ac |
|       |       |       |       |       |       |       | etami |
|       |       |       |       |       |       |       | de "w |
|       |       |       |       |       |       |       | ikili |
|       |       |       |       |       |       |       | nk")\ |
|       |       |       |       |       |       |       | *(Et  |
|       |       |       |       |       |       |       | hanam |
|       |       |       |       |       |       |       | ide)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 8     | Ami  | [Pr   | R     | ![Pr  | a     | -     | !     |
|       | nes | y#A " |       |  amin |       |       | amine |
|       |       | wikil |       | e"){w |       |       | "){wi |
|       |       | ink") |       | idth= |       |       | dth=" |
|       |       |       |       | "75"} |       |       | 75"}\ |
|       |       |       |       |       |       |       | Meth |
|       |       |       |       |       |       |       | ylami |
|       |       |       |       |       |       |       | ne\ |
|       |       |       |       |       |       |       | *(Met |
|       |       |       |       |       |       |       | hanam |
|       |       |       |       |       |       |       | ine)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| Seco | R     | !     | a     | -     | ![    |       |       |
| ndary | ~2~NH | [Seco | mino- | amine | dimet |       |       |
| am    |       | ndary |       |       | hylam |       |       |
| ine |       |       | D.png |       |       |
| ossar |       | .png  |       |       |  "dim |       |       |
| y#A " |       | "Seco |       |       | ethyl |       |       |
| wikil |       | ndary |       |       | amine |       |       |
| ink") |       |  amin |       |       | "){wi |       |       |
|       |       | e"){w |       |       | dth=" |       |       |
|       |       | idth= |       |       | 75"}\ |       |       |
|       |       | "75"} |       |       | Di   |       |       |
|       |       |       |       |       | methy |       |       |
|       |       |       |       |       | lamin |       |       |
|       |       |       |       |       | e |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| Ter  | R~3~N | ![Ter | a     | -     | !     |       |       |
| tiary |       | tiary | mino- | amine | [trim |       |       |
| am    |       | am    |       |       | ethyl |       |       |
| ine.png |       |       | e_che |       |       |
| ossar |       |  "Ter |       |       | mical |       |       |
| y#A " |       | tiary |       |       | _stru |       |       |
| wikil |       |  amin |       |       | cture |       |       |
| ink") |       | e"){w |       |       | .png  |       |       |
|       |       | idth= |       |       | "trim |       |       |
|       |       | "75"} |       |       | ethyl |       |       |
|       |       |       |       |       | amine |       |       |
|       |       |       |       |       | "){wi |       |       |
|       |       |       |       |       | dth=" |       |       |
|       |       |       |       |       | 75"}\ |       |       |
|       |       |       |       |       | Trim |       |       |
|       |       |       |       |       | ethyl |       |       |
|       |       |       |       |       | amine |       |       |
|       |       |       |       |       |  |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| [4°   | R~4   | ![    | amm   | -amm  | ![Cho |       |       |
| amm   | ~N^+^ | Quate | onio- | onium | line] |       |       |
| onium |       | rnary |       |       | (Chol |       |       |
| ion   |       | amm   |       |       | ine-s |       |       |
| ](Qua |       | onium |       |       | kelet |       |       |
| terna |       | catio |       |       | al.sv |       |       |
| ry_am |       | n](Qu |       |       | g "Ch |       |       |
| moniu |       | atern |       |       | oline |       |       |
| m_cat |       | ary-a |       |       | "){wi |       |       |
| ion " |       | mmoni |       |       | dth=" |       |       |
| wikil |       | um-ca |       |       | 75"}\ |       |       |
| ink") |       | tion. |       |       |      |       |       |
|       |       | svg " |       |       | Choli |       |       |
|       |       | Quate |       |       | ne |       |       |
|       |       | n"){w |       |       |       |       |       |
|       |       | idth= |       |       |       |       |       |
|       |       | "75"} |       |       |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 9     | Azo  | [Azo\ | RN~   | ![Az  | azo-  | -di   | ![M   |
|       | compo | (Diim | 2~R\' | o.png |       | azene | ethyl |
|       | und] |       | l](Az |       |       | orang |
|       | Organ | (Azo_ |       | o-gro |       |       | e](Me |
|       | ic_Ch | compo |       | up.pn |       |       | thyl- |
|       | emist | und " |       | g "Az |       |       | orang |
|       | ry/Gl | wikil |       | o.png |       |       | e-ske |
|       | ossar | ink") |       | l"){w |       |       | letal |
|       | y#A " |       |       | idth= |       |       | .png  |
|       | wikil |       |       | "75"} |       |       | "Meth |
|       | ink") |       |       |       |       |       | yl or |
|       |       |       |       |       |       |       | ange" |
|       |       |       |       |       |       |       | ){wid |
|       |       |       |       |       |       |       | th="1 |
|       |       |       |       |       |       |       | 50"}\ |
|       |       |       |       |       |       |       | M    |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | orang |
|       |       |       |       |       |       |       | e |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 10    | To   | Ben  | RCH~2 | ![B   | be    | 1-(*  | ![B   |
|       | luene | zylto | omide |
|       | ive{w |       |       | e-ske |
|       | ry/Gl | wikil |       | idth= |       |       | letal |
|       | ossar | ink") |       | "75"} |       |       | .svg  |
|       | y#T " |       |       |       |       |       | "Benz |
|       | wikil |       |       |       |       |       | yl br |
|       | ink") |       |       |       |       |       | omide |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | [B    |
|       |       |       |       |       |       |       | enzyl |
|       |       |       |       |       |       |       | bro   |
|       |       |       |       |       |       |       | mide] |
|       |       |       |       |       |       |       | (w:Be |
|       |       |       |       |       |       |       | nzyl_ |
|       |       |       |       |       |       |       | bromi |
|       |       |       |       |       |       |       | de "w |
|       |       |       |       |       |       |       | ikili |
|       |       |       |       |       |       |       | nk")\ |
|       |       |       |       |       |       |       | *(1   |
|       |       |       |       |       |       |       | -Brom |
|       |       |       |       |       |       |       | otolu |
|       |       |       |       |       |       |       | ene)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 11    | C    | [Carb | R     | !     |       | alkyl |       |
|       | arbon | onate | OCOOR | [Carb |       | **c   |       |
|       | ate |       | l.svg |       |       |       |
|       | wikil |       |       |  "Car |       |       |       |
|       | ink") |       |       | bonat |       |       |       |
|       |       |       |       | e"){w |       |       |       |
|       |       |       |       | idth= |       |       |       |
|       |       |       |       | "75"} |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 12    | Car  | [C    | RC    | ![Car | car   | -oate | ![S   |
|       | boxyl | arbox | OO^−^ | boxyl | boxy- |       | odium |
|       | ate |       | e-hyb |       |       | D-ske |
|       | y#C " |       |       | rid.p |       |       | letal |
|       | wikil |       |       | ng "C |       |       | .png  |
|       | ink") |       |       | arbox |       |       | "Sodi |
|       |       |       |       | ylate |       |       | um ac |
|       |       |       |       | "){wi |       |       | etate |
|       |       |       |       | dth=" |       |       | "){wi |
|       |       |       |       | 75"}\ |       |       | dth=" |
|       |       |       |       | !C   |       |       | 75"}\ |
|       |       |       |       | arbox |       |       | [S    |
|       |       |       |       | ylate |       |       | odium |
|       |       |       |       | \ |
|       |       |       |       | xylat |       |       | *(S   |
|       |       |       |       | e"){w |       |       | odium |
|       |       |       |       | idth= |       |       | e     |
|       |       |       |       | "75"} |       |       | thano |
|       |       |       |       |       |       |       | ate)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 13    |      | [     | RCOOH | ![    | car   | -oic  | ![A   |
|       | Carbo | Carbo |       | Carbo | boxy- | acid  | cetic |
|       | xylic | xyl |       | c-aci |       |       | d-2D- |
|       | emist |       |       | d-ske |       |       | skele |
|       | ry/Gl |       |       | letal |       |       | tal.s |
|       | ossar |       |       | .svg  |       |       | vg "A |
|       | y#C " |       |       | "Carb |       |       | cetic |
|       | wikil |       |       | oxyli |       |       |  acid |
|       | ink") |       |       | c aci |       |       | "){wi |
|       |       |       |       | d"){w |       |       | dth=" |
|       |       |       |       | idth= |       |       | 75"}\ |
|       |       |       |       | "75"} |       |       | A    |
|       |       |       |       |       |       |       | cetic |
|       |       |       |       |       |       |       | ac    |
|       |       |       |       |       |       |       | id\ |
|       |       |       |       |       |       |       | *(Eth |
|       |       |       |       |       |       |       | anoic |
|       |       |       |       |       |       |       | a     |
|       |       |       |       |       |       |       | cid)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 14    | [     | [Cya  | ROCN  | !     | cya   | alkyl |       |
|       | Cyana | nate] |       | Cyan | nato- | *     |       |
|       | tes |       | oup.p |       |       |       |
|       | ry/Gl |       |       | ng "C |       |       |       |
|       | ossar |       |       | yanat |       |       |       |
|       | y#C " |       |       | e"){w |       |       |       |
|       | wikil |       |       | idth= |       |       |       |
|       | ink") |       |       | "75"} |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| Thi  | RSCN  | ![T   | th    | alkyl |       |       |       |
| ocyan |       | hiocy | iocya | **thi |       |       |       |
| ate |       | e"){w |       |       |       |       |       |
|       |       | idth= |       |       |       |       |       |
|       |       | "75"} |       |       |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 15    | Et   | [Ethe | ROR\' | ![Et  | al    | alkyl | ![Di  |
|       | her |       | eral) |       |       | iethy |
|       | ry/Gl |       |       | .png  |       |       | l_eth |
|       | ossar |       |       | "Ethe |       |       | er_ch |
|       | y#C " |       |       | r"){w |       |       | emica |
|       | wikil |       |       | idth= |       |       | l_str |
|       | ink") |       |       | "75"} |       |       | uctur |
|       |       |       |       |       |       |       | e.svg |
|       |       |       |       |       |       |       |  "Die |
|       |       |       |       |       |       |       | thyl  |
|       |       |       |       |       |       |       | ether |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | Di   |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | ether |
|       |       |       |       |       |       |       | \ |
|       |       |       |       |       |       |       | *     |
|       |       |       |       |       |       |       | (Etho |
|       |       |       |       |       |       |       | xyeth |
|       |       |       |       |       |       |       | ane)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 16    | Es   | [Este | RC    | ![    |       | -oate | ![    |
|       | ter |       | ter-s |       |       | (Ethy |
|       | ry/Gl |       |       | kelet |       |       | l_but |
|       | ossar |       |       | al.pn |       |       | yrate |
|       | y#E " |       |       | g "Es |       |       | .png  |
|       | wikil |       |       | ter|7 |       |       | "Ethy |
|       | ink") |       |       | 5px") |       |       | l but |
|       |       |       |       |       |       |       | yrate |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | [     |
|       |       |       |       |       |       |       | Ethyl |
|       |       |       |       |       |       |       | buty  |
|       |       |       |       |       |       |       | rate] |
|       |       |       |       |       |       |       | (w:Et |
|       |       |       |       |       |       |       | hyl_b |
|       |       |       |       |       |       |       | utyra |
|       |       |       |       |       |       |       | te "w |
|       |       |       |       |       |       |       | ikili |
|       |       |       |       |       |       |       | nk")\ |
|       |       |       |       |       |       |       | *(    |
|       |       |       |       |       |       |       | Ethyl |
|       |       |       |       |       |       |       | b     |
|       |       |       |       |       |       |       | utano |
|       |       |       |       |       |       |       | ate)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 17    | [Ha   | [     | RX    | ![H   | halo- | alkyl | ![Chl |
|       | loalk | Halo] |       | alide |       | **hal | oroet |
|       | ane]( | (Halo |       | g     |       | ide** | hane] |
|       | Organ | gen " |       | roup] |       |       | (Chlo |
|       | ic_Ch | wikil |       | (Hali |       |       | roeth |
|       | emist | ink") |       | de-gr |       |       | ane-s |
|       | ry/Gl |       |       | oup.s |       |       | kelet |
|       | ossar |       |       | vg "H |       |       | al.pn |
|       | y#H " |       |       | alide |       |       | g "Ch |
|       | wikil |       |       |  grou |       |       | loroe |
|       | ink") |       |       | p"){w |       |       | thane |
|       |       |       |       | idth= |       |       | "){wi |
|       |       |       |       | "75"} |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | C    |
|       |       |       |       |       |       |       | hloro |
|       |       |       |       |       |       |       | ethan |
|       |       |       |       |       |       |       | e\ |
|       |       |       |       |       |       |       | *(    |
|       |       |       |       |       |       |       | Ethyl |
|       |       |       |       |       |       |       | chlor |
|       |       |       |       |       |       |       | ide)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 18    | Hyd   | H    | ROOH  | ![H   | hy    | alkyl | ![M   |
|       | roper | ydrop |       | ydrop | drope | **    | ethyl |
|       | oxide | eroxy |       | eroxy | roxy- | hydro | ethyl |
|       | (see  |  |       | png " |       |       | yl-et |
|       | rgani |       |       | Hydro |       |       | hyl-k |
|       | c_Che |       |       | perox |       |       | etone |
|       | mistr |       |       | y"){w |       |       | -pero |
|       | y/Glo |       |       | idth= |       |       | xide- |
|       | ssary |       |       | "75"} |       |       | 2D-sk |
|       | #O "w |       |       |       |       |       | eleta |
|       | ikili |       |       |       |       |       | l.png |
|       | nk")) |       |       |       |       |       |  "Met |
|       |       |       |       |       |       |       | hyl e |
|       |       |       |       |       |       |       | thyl  |
|       |       |       |       |       |       |       | keton |
|       |       |       |       |       |       |       | e per |
|       |       |       |       |       |       |       | oxide |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | M    |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | k     |
|       |       |       |       |       |       |       | etone |
|       |       |       |       |       |       |       | pe    |
|       |       |       |       |       |       |       | roxid |
|       |       |       |       |       |       |       | e |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 19    | Im   | Pr    | RC(=N | ![I   | i     | -     |       |
|       | ineR\' | mine] | mino- | imine |       |
|       | Organ | ket   |       | (Imin |       |       |       |
|       | ic_Ch | imine |       | e-(pr |       |       |       |
|       | emist |       |       | imary |       |       |       |
|       | ry/Gl |       |       | )-ske |       |       |       |
|       | ossar |       |       | letal |       |       |       |
|       | y#I " |       |       | .svg  |       |       |       |
|       | wikil |       |       | "Imin |       |       |       |
|       | ink") |       |       | e"){w |       |       |       |
|       |       |       |       | idth= |       |       |       |
|       |       |       |       | "75"} |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| Seco  | R     | !Imi | i     | -     |       |       |       |
| ndary | C(=NR | neR{ | ndary |       |       |       |       |       |
|       | {\'}} | )-ske |       |       |       |       |       |
|       |       | letal |       |       |       |       |       |
|       |       | .svg  |       |       |       |       |       |
|       |       | "Imin |       |       |       |       |       |
|       |       | e"){w |       |       |       |       |       |
|       |       | idth= |       |       |       |       |       |
|       |       | "75"} |       |       |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| Pr    | RC(   | !     | i     | -     |       |       |       |
| imary | =NH)H | Imin | mino- | imine |       |       |       |
| ald   |       | e-ske |       |       |       |       |       |
|       |       | letal |       |       |       |       |       |
|       |       | .svg  |       |       |       |       |       |
|       |       | "Imin |       |       |       |       |       |
|       |       | e"){w |       |       |       |       |       |
|       |       | idth= |       |       |       |       |       |
|       |       | "75"} |       |       |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| Seco  | RC(=N | ![I   | i     | -     |       |       |       |
| ndary | R\')H | mine] | mino- | imine |       |       |       |
| ald   |       | (Aldi |       |       |       |       |       |
| imine |       | mine- |       |       |       |       |       |
|       |       | (seco |       |       |       |       |       |
|       |       | ndary |       |       |       |       |       |
|       |       | )-ske |       |       |       |       |       |
|       |       | letal |       |       |       |       |       |
|       |       | .svg  |       |       |       |       |       |
|       |       | "Imin |       |       |       |       |       |
|       |       | e"){w |       |       |       |       |       |
|       |       | idth= |       |       |       |       |       |
|       |       | "75"} |       |       |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 20    | Is   | [Isoc | RNC   |       | isoc  | alkyl |       |
|       | ocyan | yanid |       |       | yano- | **is  |       |
|       | ide |       |       |       |       |       |
|       | ossar |       |       |       |       |       |       |
|       | y#I " |       |       |       |       |       |       |
|       | wikil |       |       |       |       |       |       |
|       | ink") |       |       |       |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 21    | Iso  | [Isoc | RNCO  | ![Iso | i     | alkyl |       |
|       | cyana | yanat |       | cyana | socya | **is  |       |
|       | tes |       | .svg  |       |       |       |
|       | ossar |       |       | "Isoc |       |       |       |
|       | y#I " |       |       | yanat |       |       |       |
|       | wikil |       |       | e"){w |       |       |       |
|       | ink") |       |       | idth= |       |       |       |
|       |       |       |       | "75"} |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| I    | RNCS  | ![    | isoth | alkyl | ![    |       |       |
| sothi |       | Isoth | iocya | **i   | Allyl |       |       |
| ocyan |       | iocya | nato- | sothi | is    |       |       |
| ate |       | yanat |       |       | letal |       |       |
|       |       | e"){w |       |       | .png  |       |       |
|       |       | idth= |       |       | "Ally |       |       |
|       |       | "75"} |       |       | l iso |       |       |
|       |       |       |       |       | thioc |       |       |
|       |       |       |       |       | yanat |       |       |
|       |       |       |       |       | "){wi |       |       |
|       |       |       |       |       | dth=" |       |       |
|       |       |       |       |       | 75"}\ |       |       |
|       |       |       |       |       | [     |       |       |
|       |       |       |       |       | Allyl |       |       |
|       |       |       |       |       | isoth |       |       |
|       |       |       |       |       | iocya |       |       |
|       |       |       |       |       | nate] |       |       |
|       |       |       |       |       | (w:Al |       |       |
|       |       |       |       |       | lyl_i |       |       |
|       |       |       |       |       | sothi |       |       |
|       |       |       |       |       | ocyan |       |       |
|       |       |       |       |       | ate " |       |       |
|       |       |       |       |       | wikil |       |       |
|       |       |       |       |       | ink") |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 22    | Ket  | [K    | R     | ![Ket | k     | -one  | ![B   |
|       | one |       | eleta |       |       | ructu |
|       | ossar |       |       | l.png |       |       | re-sk |
|       | y#K " |       |       |  "Ket |       |       | eleta |
|       | wikil |       |       | one|7 |       |       | l.png |
|       | ink") |       |       | 5px") |       |       |  "But |
|       |       |       |       |       |       |       | anone |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | [M    |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | ke    |
|       |       |       |       |       |       |       | tone] |
|       |       |       |       |       |       |       | (w:Me |
|       |       |       |       |       |       |       | thyl_ |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | _keto |
|       |       |       |       |       |       |       | ne "w |
|       |       |       |       |       |       |       | ikili |
|       |       |       |       |       |       |       | nk")\ |
|       |       |       |       |       |       |       | *(    |
|       |       |       |       |       |       |       | Butan |
|       |       |       |       |       |       |       | one)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 23    | Nitr | [Nit  | RCN   | ![N   | c     | alk   | ![Be  |
|       | ile |       | ec).s |       | *     | itril |
|       | ossar |       |       | vg "N |       | *cyan | e_str |
|       | y#N " |       |       | itril |       | ide** | uctur |
|       | wikil |       |       | e"){w |       |       | e.png |
|       | ink") |       |       | idth= |       |       |  "Ben |
|       |       |       |       | "75"} |       |       | zonit |
|       |       |       |       |       |       |       | rile  |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | B    |
|       |       |       |       |       |       |       | enzon |
|       |       |       |       |       |       |       | itril |
|       |       |       |       |       |       |       | e\ |
|       |       |       |       |       |       |       | *(P   |
|       |       |       |       |       |       |       | henyl |
|       |       |       |       |       |       |       | cyan  |
|       |       |       |       |       |       |       | ide)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 24    | [     | [N    | R     | ![Nit | n     |       | ![    |
|       | Nitro | itro] | NO~2~ | ro](N | itro- |       | Nitro |
|       | compo | (Nitr |       | itro- |       |       | metha |
|       | und]( | o_fun |       | group |       |       | ne](N |
|       | Organ | ction |       | .png  |       |       | itrom |
|       | ic_Ch | al_gr |       | "Nitr |       |       | ethan |
|       | emist | oup " |       | o"){w |       |       | e2.pn |
|       | ry/Gl | wikil |       | idth= |       |       | g "Ni |
|       | ossar | ink") |       | "75"} |       |       | trome |
|       | y#N " |       |       |       |       |       | thane |
|       | wikil |       |       |       |       |       | "){wi |
|       | ink") |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       |      |
|       |       |       |       |       |       |       | Nitro |
|       |       |       |       |       |       |       | metha |
|       |       |       |       |       |       |       | ne |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 25    | [Ni   | [Nit  | RNO   | ![    | nit   |       | ![    |
|       | troso | roso] |       | Nitro | roso- |       | Nitro |
|       | compo | (Nitr |       | so](N |       |       | soben |
|       | und]( | oso " |       | itros |       |       | zene] |
|       | Organ | wikil |       | o-com |       |       | (Nitr |
|       | ic_Ch | ink") |       | pound |       |       | osobe |
|       | emist |       |       | -2D.p |       |       | nzene |
|       | ry/Gl |       |       | ng "N |       |       | .png  |
|       | ossar |       |       | itros |       |       | "Nitr |
|       | y#N " |       |       | o"){w |       |       | osobe |
|       | wikil |       |       | idth= |       |       | nzene |
|       | ink") |       |       | "75"} |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | Nitr |
|       |       |       |       |       |       |       | osobe |
|       |       |       |       |       |       |       | nzene |
|       |       |       |       |       |       |       |  |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 26    |      | P    | ROOR  | ![P   | pe    | alkyl | ![Di- |
|       | Perox | eroxy |       | eroxy | roxy- | **    | tert- |
|       | ide |       | y"){w |       |       | tyl_p |
|       | y#P " |       |       | idth= |       |       | eroxi |
|       | wikil |       |       | "75"} |       |       | de.sv |
|       | ink") |       |       |       |       |       | g "Di |
|       |       |       |       |       |       |       | -tert |
|       |       |       |       |       |       |       | -buty |
|       |       |       |       |       |       |       | l per |
|       |       |       |       |       |       |       | oxide |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | Di-  |
|       |       |       |       |       |       |       | tert- |
|       |       |       |       |       |       |       | butyl |
|       |       |       |       |       |       |       | p     |
|       |       |       |       |       |       |       | eroxi |
|       |       |       |       |       |       |       | de |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 27    | Be   | [P    | RC~6  | ![P   | ph    | -be   | ![Cum |
|       | nzene | henyl | ~H~5~ | henyl | enyl- | nzene | ene |       | png " |       |       | tal.p |
|       | ic_Ch |       |       | Pheny |       |       | ng "C |
|       | emist |       |       | l"){w |       |       | umene |
|       | ry/Gl |       |       | idth= |       |       | "){wi |
|       | ossar |       |       | "75"} |       |       | dth=" |
|       | y#B " |       |       |       |       |       | 75"}\ |
|       | wikil |       |       |       |       |       | Cume |
|       | ink") |       |       |       |       |       | ne\ |
|       |       |       |       |       |       |       | *(2-  |
|       |       |       |       |       |       |       | pheny |
|       |       |       |       |       |       |       | lprop |
|       |       |       |       |       |       |       | ane)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 28    | P    | Phos  | R~3~P | ![A   | phosp | -phos | ![    |
|       | hosph | phino |       | ter   | hino- | phane | Methy |
|       | ine |       |       | "A te |       |       | skele |
|       |       |       |       | rtiar |       |       | tal.s |
|       |       |       |       | y pho |       |       | vg "M |
|       |       |       |       | sphin |       |       | ethyl |
|       |       |       |       | e"){w |       |       | propy |
|       |       |       |       | idth= |       |       | lphos |
|       |       |       |       | "75"} |       |       | phane |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | M     |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | propy |
|       |       |       |       |       |       |       | lphos |
|       |       |       |       |       |       |       | phane |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 29    | P    | [Ph   | H     | ![    | phosp | di    | [DN   |
|       | hosph | ospha | OPO(O | Phosp | horic | (*sub | A~2~ | hodie | acid  | stitu | DNA " |
|       | ter | wikil |
|       | Organ | ate " |       | (Phos | (*sub | hy    | ink") |
|       | ic_Ch | wikil |       | phodi | stitu | droge |       |
|       | emist | ink") |       | ester | ent*) | nphos |       |
|       | ry/Gl |       |       | -grou | ester | phate |       |
|       | ossar |       |       | p.png |       |       |       |
|       | y#P " |       |       |  "Pho |       |       |       |
|       | wikil |       |       | sphod |       |       |       |
|       | ink") |       |       | ieste |       |       |       |
|       |       |       |       | r"){w |       |       |       |
|       |       |       |       | idth= |       |       |       |
|       |       |       |       | "75"} |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 30    |      | Phos  | RP(   | !     | phosp | *su   | !B   |
|       | Phosp | phono | =O)(O | [Phos | hono- | bstit | enzyl |
|       | honic |       | H)~2~ | phono |       | uent* | phosp |
|       | a     |       |       | group |       | phosp | honic |
|       | cid |       |       |  grou |       |       | tal.p |
|       |       |       |       | p"){w |       |       | ng "B |
|       |       |       |       | idth= |       |       | enzyl |
|       |       |       |       | "75"} |       |       | phosp |
|       |       |       |       |       |       |       | honic |
|       |       |       |       |       |       |       |  acid |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | B     |
|       |       |       |       |       |       |       | enzyl |
|       |       |       |       |       |       |       | phosp |
|       |       |       |       |       |       |       | honic |
|       |       |       |       |       |       |       | acid  |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 31    | P    | Phos  | ROP(  | !     | pho   |       | !     |
|       | hosph | phate | =O)(O | [Phos | spho- |       | [Glyc |
|       | ate~2~ | phate |       |       | erald |
|       | Organ |       |       | gr    |       |       | ehyde |
|       | ic_Ch |       |       | oup |       |       | phate |       |       | ng "G |
|       |       |       |       |  grou |       |       | lycer |
|       |       |       |       | p"){w |       |       | aldeh |
|       |       |       |       | idth= |       |       | yde 3 |
|       |       |       |       | "75"} |       |       | -phos |
|       |       |       |       |       |       |       | phate |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | Glyc |
|       |       |       |       |       |       |       | erald |
|       |       |       |       |       |       |       | ehyde |
|       |       |       |       |       |       |       | 3-p   |
|       |       |       |       |       |       |       | hosph |
|       |       |       |       |       |       |       | ate |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 32    | Pyr  | Pyri | RC~5~ | !     | 4-pyr | -pyr  | !     |
|       | idine | dyl\ |       | tine- |
|       | Organ | ink") |       | 4-pyr | \     |       | 2D-sk |
|       | ic_Ch |       |       | idyl. | 3-pyr |       | eleta |
|       | emist |       |       | svg " | idyl\ |       | l.png |
|       | ry/Gl |       |       | 4-pyr | (pyri |       |  "Nic |
|       | ossar |       |       | idyl  | din-3 |       | otine |
|       | y#P " |       |       | group | -yl)\ |       | "){wi |
|       | wikil |       |       | "){wi | \     |       | dth=" |
|       | ink") |       |       | dth=" | 2-pyr |       | 75"}\ |
|       |       |       |       | 75"}\ | idyl\ |       | Ni   |
|       |       |       |       | !     | (pyr  |       | cotin |
|       |       |       |       | [3-py | idin- |       | e |       | Nicot |
|       |       |       |       | gr    |       |       | ine " |
|       |       |       |       | oup |
|       |       |       |       | idyl. |       |       |       |
|       |       |       |       | svg " |       |       |       |
|       |       |       |       | 3-pyr |       |       |       |
|       |       |       |       | idyl  |       |       |       |
|       |       |       |       | group |       |       |       |
|       |       |       |       | "){wi |       |       |       |
|       |       |       |       | dth=" |       |       |       |
|       |       |       |       | 75"}\ |       |       |       |
|       |       |       |       | !     |       |       |       |
|       |       |       |       | 2-py |       |       |       |
|       |       |       |       | ridyl |       |       |       |
|       |       |       |       | gr    |       |       |       |
|       |       |       |       | oup{wi |       |       |       |
|       |       |       |       | dth=" |       |       |       |
|       |       |       |       | 75"}\ |       |       |       |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 33    | Sulf |       | RSR\' | !Su  |       | di    | ![Dim |
|       | ide | ulfid |
|       | emist |       |       | (Sulf |       | su    | e |       |       | lfide |       |       | imeth |
|       |       |       |       |  grou |       |       | yl su |
|       |       |       |       | p"){w |       |       | lfide |
|       |       |       |       | idth= |       |       | "){wi |
|       |       |       |       | "75"} |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | Dim  |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | sulf  |
|       |       |       |       |       |       |       | ide |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 34    | Sulf | Sulf | RSO~  | ![Sul | sulf  | di    | ![Dim |
|       | one | ulfon |
|       | emist | wikil |       | ulfon |       | su    | e |       | e.png |       | lfone | SO2.s |
|       | ossar |       |       |  "Sul |       |       | vg "D |
|       | y#S " |       |       | fonyl |       |       | imeth |
|       | wikil |       |       |  grou |       |       | yl su |
|       | ink") |       |       | p"){w |       |       | lfone |
|       |       |       |       | idth= |       |       | "){wi |
|       |       |       |       | "75"} |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | Dim   |
|       |       |       |       |       |       |       | ethyl |
|       |       |       |       |       |       |       | sul   |
|       |       |       |       |       |       |       | fone\ |
|       |       |       |       |       |       |       | *(   |
|       |       |       |       |       |       |       | Methy |
|       |       |       |       |       |       |       | lsulf |
|       |       |       |       |       |       |       | onylm |
|       |       |       |       |       |       |       | ethan |
|       |       |       |       |       |       |       | e)* |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 35    | Sul  | Sulfo | RS    | !Sul | s     | *su   | ![    |
|       | fonic |       | O~3~H | fonyl | ulfo- | bstit | Benze |
|       | a     |       |       | grou  |       | uent* | nesul |
|       | cid{w |       |       | -skel |
|       | ink") |       |       | idth= |       |       | etal. |
|       |       |       |       | "75"} |       |       | png " |
|       |       |       |       |       |       |       | Benze |
|       |       |       |       |       |       |       | nesul |
|       |       |       |       |       |       |       | fonic |
|       |       |       |       |       |       |       |  acid |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | Benze |
|       |       |       |       |       |       |       | nesul |
|       |       |       |       |       |       |       | fonic |
|       |       |       |       |       |       |       | acid  |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 36    | S    | [S    | R     | ![Sul | sulf  | di    | ![Dip |
|       | ulfox | ulfin | SOR\' | finyl | inyl- | (*sub | henyl |
|       | ide | foxid |
|       | ic_Ch | ide " |       | foxid |       | **s   | e |       |  "Sul |       | ide** | l-sul |
|       | ossar |       |       | finyl |       |       | foxid |
|       | y#S " |       |       |  grou |       |       | e.png |
|       | wikil |       |       | p"){w |       |       |  "Dip |
|       | ink") |       |       | idth= |       |       | henyl |
|       |       |       |       | "75"} |       |       |  sulf |
|       |       |       |       |       |       |       | oxide |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | Dip   |
|       |       |       |       |       |       |       | henyl |
|       |       |       |       |       |       |       | sulf  |
|       |       |       |       |       |       |       | oxide |
+-------+-------+-------+-------+-------+-------+-------+-------+
| 37    | Th   | Sulf | RSH   | ![Sul | merca | -     | ![    |
|       | iol |       | .png  |       |       | hiol- |
|       | ossar |       |       | "Sulf |       |       | skele |
|       | y#T " |       |       | hydry |       |       | tal.s |
|       | wikil |       |       | l"){w |       |       | vg "E |
|       | ink") |       |       | idth= |       |       | thane |
|       |       |       |       | "75"} |       |       | thiol |
|       |       |       |       |       |       |       | "){wi |
|       |       |       |       |       |       |       | dth=" |
|       |       |       |       |       |       |       | 75"}\ |
|       |       |       |       |       |       |       | Etha |
|       |       |       |       |       |       |       | nethi |
|       |       |       |       |       |       |       | ol\ |
|       |       |       |       |       |       |       | *(    |
|       |       |       |       |       |       |       | Ethyl |
|       |       |       |       |       |       |       | m     |
|       |       |       |       |       |       |       | ercap |
|       |       |       |       |       |       |       | tan)* |
+-------+-------+-------+-------+-------+-------+-------+-------+

*Note: The table above is adapted from the Functional Groups table on
Wikipedia.*

Combining the names of functional groups with the names of the parent
alkanes generates a powerful systematic
nomenclature for naming organic
compounds.

The non-hydrogen atoms of functional groups are always associated with
each by covalent bonds, as well as with
the rest of the molecule. When the group of atoms is associated with the
rest of the molecule primarily by ionic forces, the group is referred to
more properly as a polyatomic ion or
complex ion. And all of these are called
radicals, by a meaning of the term *radical*
that predates the free radical.

The first carbon after the carbon that attaches to the functional group
is called the alpha carbon.

Alcohol containing two hydroxyl groups are called glycols. They have
both common names and IUPAC names.

## Mnemonics for Functional Groups

These are possible mnemonics for the common functional groups.

`<b>`{=html}Vowels`</b>`{=html}: Remember the vowels \"A\", \"E\", and
\"Y\" for Alkane, Alkene, and Alkyne. Alkanes have only single covalent
bonds. Alkenes have at least one double bond. Alkynes have at least one
triple bond. The letters \"I\", \"O\", and \"U\" are not used.
Furthermore, \"O\" and \"U\" would result in awkward pronunciations.

`<b>`{=html}Alcohol`</b>`{=html}: Look for the \"C-O-H\" in \"Alcohol.\"

`<b>`{=html}Ether`</b>`{=html}: Ethers were anesthetics used in the
1800s. Dr. Kellogg also lived at the same time. Corn Flakes are made by
Kellogg\'s. A rooster or cock (C-O-C) is the cornflake mascot. Or, think
there is a C on \"either\" side of the O.

`<b>`{=html}Amine`</b>`{=html}: Remember the \"N\" stands for nitrogen.

`<b>`{=html}Aldehyde`</b>`{=html}: This sounds like \"Adelaide,\" the
Australian city. Australia is at the end of the Asian islands, and
aldehydes are at the end of the hydrocarbon chain. The \"Y\" indicates a
C=O double bond.

`<b>`{=html}Ketone`</b>`{=html}: Imagine the diagonal strokes of \"K\"
forming the C=O double bond.
![

`<b>`{=html}Carboxylic Acid`</b>`{=html}: \"Box\" stands for boxed wine
or C-O-H, alcohol. The \"Y\" indicates a C=O double bond.

`<b>`{=html}Ester`</b>`{=html}: This sounds like \"Estelle\" George
Costanza\'s mother in the TV show _Seinfeld_.
George\'s nickname was Koko or Coco. So think of O=C-O-C.

`<b>`{=html}Amide`</b>`{=html}: Amine with a \"D\". D for double.


# Organic Chemistry/Haloalkanes

**Haloalkanes** are otherwise simple alkanes that contain one or more
members of the halogen family. In practice, the halogens found in
organic molecules are chlorine (Cl), bromine (Br), fluorine (F), and
iodine (I). Some texts refer to this class of compounds as
**halogenoalkanes** or **alkyl halides**. This text (and the chemical
literature) will frequently use the terms **haloalkane** and **alkyl
halide** interchangeably.

*Note:* The X in R-X represents a generic halogen atom.

# Preparation

Methods for preparation are found elsewhere in this text:

-   Preparation from
    Alcohols
    (nucleophilic substitution)

```{=html}
<!-- -->
```
-   Preparation from /Alkanes/ (radical
    substitution)

```{=html}
<!-- -->
```
-   Preparation from
    Alkenes
    (electrophilic addition)
-   Preparation by halogen exchange.\*It is generally used for preparing
    iodoalkanes.
-   Preparation from silver salts of acids\*

# Properties

## Naming Haloalkanes

Haloalkanes are named by adding a prefix to the name of the alkane from
which they are derived. The prefix denotes the particular halogen used.

**F** = *Fluoro-*\
**Cl** = *Chloro-*\
**Br** = *Bromo-*\
**I** = *Iodo-*\
If other substituents need to be named, all prefixes are still put in
alphabetical order. When necessary, numbers identify substituent
locations.

### Example names of haloalkanes

  ---------------------------------------------------------------------------------- --------------------------------------- ----------------------
                                                                                **IUPAC name**                          **Common name**
  CH~3~---F                                                                          Fluoromethane                           Methyl fluoride
  CH~3~---Cl                                                                         Chloromethane                           Methyl chloride
  CH~3~---Br                                                                         Bromomethane                            Methyl bromide
  CH~3~---I                                                                          Iodomethane                             Methyliodide
  F---CH~2~---F                                                                      Difluoromethane                         Methylene fluoride
  Cl---CH~2~---Cl                                                                    Dichloromethane                         Methylene chloride
  F---CH~2~---Cl                                                                     Chlorofluoromethane
  CHBrClF                                                                            Bromochlorofluoromethane
  HCCl~3~                                                                            Trichloromethane                        Chloroform
  CHX~3~                                                                             Haloforms (X=halogen)
  CCl~4~                                                                             Tetrachloromethane                      Carbon tetrachloride
  CH~3~CHCl~2~                                                                       1,1-Dichloroethane
  ![]((Dibromomethyl)cyclohexane.svg "(Dibromomethyl)cyclohexane.svg"){width="75"}   (Dibromomethyl)cyclohexane
  ![](Dibromomethylcyclohexane2.png "Dibromomethylcyclohexane2.png")                 Equatorial (Dibromomethyl)cyclohexane
  ![](1,6-Dichloro-2,3,5-trimethy.png "1,6-Dichloro-2,3,5-trimethy.png")             1,6-Dichloro-2,5-dimethylhexane
  !50 px                             1,1-Dichloro-3-methylcyclobutane
  ---------------------------------------------------------------------------------- --------------------------------------- ----------------------

## Physical properties

**R-X bond polarity:** C---F \> C---Cl \> C---Br \> C---I

  ------------- -------------------------- ----------------------------------
  **atom** \|   **electronegativity** \|   **difference from C** (= 2.5) \|
  F             4.0                        1.5
  Cl            3.0                        0.5
  Br            2.8                        0.3
  I             2.5                        0.0
  ------------- -------------------------- ----------------------------------

The difference in electronegativity of the carbon-halogen bonds range
from 1.5 in C-F to almost 0 in C-I. This means that the C-F bond is
extremely polar, though not ionic, and the C-I bond is almost nonpolar.

**Physical appearance:** Haloalkanes are colourless when pure. However
bromo and iodo alkanes develop colour when exposed to light. Many
volatile halogen compounds have sweet smell.

**Boiling point:** Haloalkanes are generally liquids at room
temperature. Haloalkanes generally have a boiling point that is higher
than the alkane they are derived from. This is due to the increased
molecular weight due to the large halogen atoms and the increased
intermolecular forces due to the polar bonds, and the increasing
polarizabilty of the halogen.

For the same alkyl group, the boiling point of haloalkanes decreases in
the order RI \> RBr \> RCl \> RF.This is due to the increase in van der
Waals forces when the size and mass
of the halogen atom increases.

For isomeric haloalkanes, the boiling point decrease with increase in
branching. But boiling points of dihalobenzenes are nearly same; however
the para-isomers have higher melting points as it fits into the crystal
lattice better when compared to ortho- and meta-isomers.

**Density:** Haloalkanes are generally more dense than the alkane they
are derived from and usually more dense than water. Density increases
with the number of carbon and halogen atom. It also increases with the
increase in mass of halogen atom.

**Solubility:** The haloalkanes are only very slightly soluble in water,
but dissolves in organic solvents. This is because for dissolving
haloalkanes in water the strong hydrogen bonds present in the latter has
to be broken. When dissolved in organic (non polar) solvents, the
intermolecular attractions are almost same as that being broken.

**Bond Length:** C---F \< C---Cl \< C---Br \< C---I

  ---------- -----------------
  **bond**   **length** (pm)
  C-F        138
  C-Cl       177
  C-Br       193
  C-I        214
  ---------- -----------------

Larger atoms means larger bond lengths, as the orbitals on the halogen
is larger the heavier the halogen is. In F, the orbitals used to make
the bonds is 2s and 2p, in Cl, it\'s 3s and 3p, in Br, 4s and 4p, and in
I, 5s and 5p. The larger the principal quantum number, the bigger the
orbital. This is somewhat offset by the larger effective nuclear charge,
but not enough to reverse the order.

## Chemical properties

**Bond strength:** C---F \> C---Cl \> C---Br \> C---I

  ---------- ---------------------------
  **bond**   **strength** (kJ mol^-1^)
  C-F        484
  C-Cl       338
  C-Br       276
  C-I        238
  ---------- ---------------------------

The orbitals C uses to make bonds are 2s and 2p. The overlap integral is
larger the closer the principal quantum number of the orbitals is, so
the overlap is larger in the bonds to lighter halogens, making the bond
formation energetically favorable.

**Bond reactivity:** C---F \< C---Cl \< C---Br \< C---I

Stronger bonds are more difficult to break, making them less reactive.
In addition, the reactivity can also be determined by the stability of
the corresponding anion formed in solution. One of the many trends on
the periodic table states that the largest atoms are located on the
bottom right corner, implying that iodine is the largest and fluorine
being the smallest. When fluorine leaves as fluoride (if it does) in the
reaction, it is not so stable compared to iodide. Because there are no
resonance forms and inductive stabilizing effects on these individual
atoms, the atoms must utilize their own inherent abilities to stabilize
themselves. Iodide has the greatest surface area out of these four
elements, which gives it the ability to better distribute its negative
charge that it has obtained. Fluorine, having the least surface area, is
much more difficult to stabilize. This is the reason why iodine is the
best leaving group out of the four halogens discussed.

# Reactions

**Determination of Haloalkanes:** A famous test used to determine if a
compound is a haloalkane is the Beilstein test, in which the compound
tested is burned in a loop of copper wire. The compound will burn green
if it is a haloalkane. The numbers of fluorine, chlorine, bromine and
iodine atoms present in each molecule can be determined using the sodium
fusion reaction, in which the compound is subjected to the action of
liquid sodium, an exceptionally strong reducing agent, which causes the
formation of sodium halide salts. Qualitative analysis can be used to
discover which halogens were present in the original compound;
quantitative analysis is used to find the quantities.

## Substitution reactions of haloalkanes

R-X bonds are very commonly used throughout organic chemistry because
their polar bonds make them reasonably reactive. In a **substitution
reaction**, the halogen (X) is replaced by another substituent (Y). The
alkyl group (R) is not changed.

  ------------------------------------------------------------------------------
  The \"**:**\" in a chemical equation represents a pair of unbound electrons.
  ------------------------------------------------------------------------------

+-------------------------------------+
| **A general substitution reaction** |
|                                     |
| Y: + R---X → R---Y + X:             |
+-------------------------------------+

Substitutions involving haloalkanes involve a type of substition called
**Nucleophilic substitution**, in which the substituent Y is a
**nucleophile**. A nucleophile is an electron pair donor. The
nucleophile replaces the halogen, an *electrophile*, which becomes a
**leaving group**. The leaving group is an electron pair acceptor.
Nuclephilic substition reactions are abbreviated as S~N~ reactions.

  ------------------------------------------
  \"Nu\" represents a generic nucleophile.
  ------------------------------------------

+---------------------------------------------+
| ```{=html}                                  |
| <H2>                                        |
| ```                                         |
| General nucleophilic substitution reactions |
|                                             |
| ```{=html}                                  |
| </H2>                                       |
| ```                                         |
| Nu:^-^ + R---X → R---Nu + X:^-^\            |
| Nu: + R---X → R---Nu^+^ + X:^-^             |
+---------------------------------------------+

  ------------- ----------------- ---------------- -------------- -------------------
  **Reagent**   **Nucleophile**   **Name**         Product        Product name
  NaOH/KOH      :O^-^H            Hydroxide        R---OH         Alcohol
  NaOR\'        :O^-^R\'          Alkoxide         R---O---R\'    Ether
                :S^-^H            Hydrosulfide     R---SH         Thiol
  NH~3~         :NH~3~            Ammonia          R---NH~3~^+^   Alkylammonium ion
  KCN           :C^-^N            Cyanide          R---CN         Nitrile
  AgCN          Ag-CN:            Silver cyanide   R-NC           isonitrile
                :C^-^≡C---H       Acetylide        R-C≡C---H      Alkyne
  NaI           :I^-^             Iodide           R---I          Alkyl Iodide
  R\'^-^M^+^    :R\'^-^           Carbanion        R-R\'          Alkane
  KNO~2~        O=N---O           Nitrite          R--O---N=O     Alkyl nitrite
  AgNO~2~       Ag---Ö---N=O      Silver nitrite   R---NO~2~      Nitroalkane
  LiAlH~4~      H                 Hydrogen         RH             alkane
  R\'COOAg      R\'COO^-^         Alkanoate        R\'COOR        Ester
  ------------- ----------------- ---------------- -------------- -------------------

  : **Common Nucleophiles**

**Example:** Suggest a reaction to produce the following molecule.

![](1-ethoxy-3-methylbutane.gif "1-ethoxy-3-methylbutane.gif")

**Answer:**

![](1-bromo-3-methylbutane.gif "1-bromo-3-methylbutane.gif")`<span style="font-size:x-large;">`{=html}+`</span>`{=html}!Ethanolate{width="150"}

`<span style="font-size:x-large;">`{=html}OR`</span>`{=html}

![](3-methylbutan-1-olate.gif "3-methylbutan-1-olate.gif")`<span style="font-size:x-large;">`{=html}+`</span>`{=html}!Bromoethane{width="120"}

*Any halogen could be used instead of Br*

### Reaction mechanisms

Nucleophilic substitution can occur in two different ways. S~N~2
involves a **backside attack**. S~N~1 involves a **carbocation
intermediate**.

**S~N~2 mechanism** !Illustration of the Sn2 mechanism. First, the
electrons in the nucleophile attack the central carbon atom from the
side opposite the leaving group (in this case, a halogen). The electrons
forming the bond between the central carbon atom and the halogen move to
the halogen, causing the halogen to leave the
molecule.. The electrons forming the bond between the central carbon atom and the halogen move to the halogen, causing the halogen to leave the molecule.")

**S~N~1 mechanism** !Illustration of the Sn1 mechanism. First, in the
presence of a polar solvent, the C-X bond breaks, forming the
carbocation. This carbocation intermediate is highly reactive. In this
case, it reacts with water. Note that the water may attack from either
side.

### Comparison of S~N~1 and S~N~2 mechanism

**Stereochemistry:**\
S~N~2 - Configuration is inverted (i.e. R to S and vice-versa).\
S~N~1 - Product is a mixture of inversion and retention of orientation
because the carbocation can be attacked from either side. In theory the
products formed are usually racemic due to the 50% chance of attack from
the planar conformation. Interestingly, the amount of the inverted
product is often up to 20% greater than the amount of product with the
original orientation. Saul Winstein has proposed that this discrepancy
occurs through the leaving group forming an ion pair with the substrate,
which temporarily shields the carbocation from attack on the side with
the leaving group.\
**Rate of reaction:**\
S~N~2 - Rate depends on concentrations of both the haloalkane and the
nucleophile. S~N~2 reactions are fast.\
S~N~1 - Rate depends only on the concentration of the haloalkane. The
carbocation forms much slower than it reacts with other molecules. This
makes S~N~1 reactions slow.\
**Role of solvent:**\
S~N~2 - Polar aprotic solvents favored. Examples: Acetone, THF (an
ether), dimethyl sulfoxide, n,n-dimethylformamide,
hexamethylphosphoramide (HMPA).\
Nonpolar solvents will also work, such as carbon tetrachloride (CCl~4~)\
Protic solvents are the worst type for S~N~2 reactions because they
\"cage,\" or solvate, the nucleophile, making it much less reactive.\
S~N~1 - Polar protic solvents favored. Examples: H~2~O, Formic acid,
methanol.\
Aprotic solvents will work also, but protic solvents are better because
they will stabilize the leaving group, which is usually negatively
charged, by solvating it. Nonpolar solvents are the worst solvent for
S~N~1 reactions because they do nothing to stabilize the carbocation
intermediate.\
**Role of nucleophile:**\
S~N~2 - Good nucleophiles favored\
S~N~1 - Any nucleophile will work (since it has no effect on reaction
rate)\
**Carbocation stability:**\
3^°^ carbon - most stable = S~N~1 favored\
2^°^ carbon - less stable = either could be favored\
1^°^ carbon - seldom forms = S~N~2 favored\
CH~3~^+^ - never forms = S~N~2 favored\
The reason why the tertiary carbocation is most favored is due to the
inductive effect. In the carbocation intermediate, there is a resulting
formal charge of +1 on the carbon that possessed the haloalkane. The
positive charge will attract the electrons available. Because this is
tertiary, meaning that adjacent carbon atoms and substituents are
available, it will provide the most electron-density to stabilize this
charge.

### Example

Predict whether the following reactions will undergo S~N~2 or S~N~1 and
tell why.

1:
![](haloalkanemechanismsproblem1.gif "haloalkanemechanismsproblem1.gif")

2:
![](haloalkanemechanismsproblem2.gif "haloalkanemechanismsproblem2.gif")

3:
![](haloalkanemechanismsproblem3.gif "haloalkanemechanismsproblem3.gif")

**Answers:**\
1) S~N~2. Good nucleophile, polar solvent.\
2) S~N~1. Tertiary carbon, polar solvent. Very slow reaction rate.\
3) S~N~2. Primary carbon, good nucleophile, nonpolar solvent.\

## Grignard reagents

Grignard reagents are created by reacting magnesium metal with a
haloalkane. The magnesium atom gets between the alkyl group and the
halogen atom with the general reaction as stated below:

R-Br + Mg → R-Mg-Br

Gringard reagents are very reactive and thus provide a means of organic
synthesis from haloalkanes. For example, adding water gives the alcohol
R-OH. Basic: R-X + Mg → R-Mg-X For example (X=Cl and R=CH3): CH3-Cl + Mg
→ CH3MgCl (methylmagnesiumchloride)

## Elimination reactions

With alcoholic potassium hydroxide, haloalkanes lose H-X and form the
corresponding alkene. Very strong bases such as KNH~2~/NH~3~ convert
vic-dihalides (haloalkanes with two halogen atoms on adjacent carbons)
into alkynes.

------------------------------------------------------------------------

\<\< Stereochemistry \|
Haloalkanes \| Alcohols \>\>


# Organic Chemistry/Alcohols

**Alcohols** are the family of compounds that contain one or more
**hydroxyl (-OH)** groups attached to a single bonded alkane. Alcohols
are represented by the general formula -OH. Alcohols are important in
organic chemistry because they can be converted to and from many other
types of compounds. Reactions with alcohols fall into two different
categories. Reactions can cleave the R-O bond or they can cleave the O-H
bond.

Ethanol (ethyl alcohol, or grain alcohol) is found in alcoholic
beverages, CH~3~CH~2~OH.

# Preparation

In the Alkenes section, we
already covered a few methods for synthesizing alcohols. One is the
hydroboration-oxidation of alkenes and the other is the
oxymercuration-reduction of alkenes. But there are a great many other
ways of creating alcohols as well.

A common source for producing alcohols is from carbonyl compounds. The
choice of carbonyl type (ketone, aldehyde, ester, etc.) and the type of
reaction (Grignard addition or Reduction), will determine the product(s)
you will get. Fortunately, there are a number of variations of
carbonyls, leading to a number of choices in product.

There are primarily two types of reactions used to create alcohols from
carbonyls: Grignard Addition reactions and Reduction reactions. We\'ll
look at each type of reaction for each type of carbonyl.

### Grignard Addition Reactions

As we learned previously, Grignard
reagents
are created by reacting magnesium metal with an alkyl halide (aka
haloalkanes). The magnesium
atom then gets between the alkyl group and the halogen atom with the
general reaction:

R-X + Mg → R-Mg-X

In our examples, we\'ll be using bromine in our Grignard reagents
because it\'s a common Grignard halogen and it will keep our examples a
little clearer without the need for X.

!Mechanism of Grignard reagent reacting with a
carbonyl{width="600"}

The general mechanism of a Grignard reagent reacting with a carbonyl
(except esters) involves the creation of a 6-membered ring transition
state. The pi bond of the oxygen attacks a neighboring magnesium bromide
which in turn, releases from its R group leaving a carbocation. At the
same time, the magnesium bromide ion from another Grignard molecule is
attacked by the carbocation and has its magnesium bromide ion stolen
(restoring it to its original state as a Grignard reagent). The second
molecule\'s carbocation is then free to attack the carbanion resulting
from the vacating pi bond, attaching the R group to the carbonyl.

According to youtube, see Grignard reagent, the carbanion (R:-) from the
R-MgBr attacks the partially positive carbonyl carbon, displacing the pi
electrons onto the O, which takes a proton, forming the alcohol.

At this point, there is a magnesium bromide on the oxygen of what was a
carbonyl. The proton from the acidic solvent easily displaces this
magnesium bromide ion and protonates the oxygen, creating a primary
alcohol with formaldehyde, a secondary alcohol with an aldehyde and a
tertiary alcohol with a ketone.

With esters, the mechanism is slightly different. Two moles of Grignard
are required for each mole of the ester. Initially, the pi bond on the
carbonyl oxygen attacks the magnesium bromide ion. This opens up the
carbon for attack from the R group of the Grignard. This part of the
reaction is slow because of the dual oxygens off of the carbon providing
some resonance stabilization. The oxygen\'s pi bond then re-forms,
expelling the O-R group of the ester which then joins with the magnesium
bromide, leaving R-O-MgBr and a ketone. The R-O-MgBr is quickly
protonated from the acidic solution and the ketone is then attacked by
Grignard reagent via the mechanism described earlier.

#### Synthesis from Formaldehyde

!Synthesis of alcohol from formaldehyde and Grignard
reagent{width="600"}

The image above shows the synthesis of an alcohol from formaldehyde
reacted with a Grignard reagent. When a formaldehyde is the target of
the Grignard\'s attack, the result is a primary alcohol.

#### Synthesis from an Aldehyde

!Synthesis of alcohol from an aldehyde and Grignard
reagent{width="600"}

The image above shows the synthesis of an alcohol from an aldehyde
reacted with a Grignard reagent. When an aldehyde is the target of the
Grignard\'s attack, the result is a secondary alcohol.

#### Synthesis from a Ketone

!Synthesis of alcohol from an ketone and Grignard
reagent{width="600"}

The image above shows the synthesis of an alcohol from a ketone reacted
with a Grignard reagent. When a ketone is the target of the Grignard\'s
attack, the result is a tertiary alcohol.

#### Synthesis from an Ester

!Synthesis of alcohol from an ester and Grignard
reagent{width="600"}

The image above shows the synthesis of an alcohol from an ester reacted
with a Grignard reagent. When an ester is the target of the Grignard\'s
attack, the result is a tertiary alcohol and a primary alcohol. The
primary alcohol is always from the -O-R portion of the ester and the
tertiary alcohol is the other R groups of the ester combined with the R
group from the Grignard reagent.

#### Synthesis from an Epoxide

!Synthesis of alcohol from an epoxide and Grignard
reagent{width="600"}

We will discuss reactions with Epoxides later when we cover epoxides,
but for now, we\'ll briefly discuss the synthesis of an alcohol from an
epoxide. The nature of the reaction is different than with the
carbonyls, as might be expected. The reaction of Grignard reagents with
epoxides is regioselective. The Grignard reagent attacks at the least
substituted side of the carbon-oxygen bonds, if there is one. In this
case, one carbon has 2 hydrogens and the other has 1, so the R group
attacks the carbon with 2 hydrogens, breaking the bond with oxygen which
is then protonated by the acidic solution. leaving a secondary alcohol
and a concatenated carbon chain. The R group can be alkyl or aryl.

#### Organolithium Alternative

As an alternative to Grignard reagents, organolithium reagents can be
used as well. Organolithium reagents are slightly more reactive, but
produce the same general results as Grignard reagents, including the
synthesis from epoxides. IT IS KNOWN AS Organolithium Alternative.

### Reduction

#### Synthesis from an Aldehyde

!Synthesis of alcohol from an aldehyde by
reduction.{width="600"}

The image above shows the synthesis of an alcohol from an aldehyde by
reduction.

#### Synthesis from a Ketone

!Synthesis of alcohol from an aldehyde by
reduction{width="600"}

The image above shows the synthesis of an alcohol from a ketone by
reduction.

#### Synthesis from an Ester

!Synthesis of alcohol from an ester by
reduction{width="600"}

The image above shows the synthesis of an alcohol from an ester by
reduction. Esters can be hydrolysed to form an alcohol and a carboxylic
acid.

#### Synthesis from a Carboxylic Acid

!Synthesis of alcohol from a carboxylic acid by
reduction{width="600"}

The image above shows the synthesis of an alcohol from a carboxylic acid
reacted by reduction.

# Properties

## Naming alcohols

Follow these rules to name alcohols the IUPAC way:

1.  find the longest carbon chain containing at least one OH group, this
    is the parent
    1.  if there are multiple OH groups, look for the chain with the
        most of them, and the way to count as many carbons in that chain
    2.  name as an alcohol, alkane diol, triol, etc.
2.  number the OH groups, giving each group the lowest number possible
    when different numbering possibilities exist
3.  treat all other groups as lower priority substituents (alcohol /
    hydroxy groups are the highest priority group for naming)

### Example alcohols

                                                                                IUPAC name                                         Common name
  --------------------------------------------------------------------------------- -------------------------------------------------- -------------------------------------------------------------------------------------------------
  CH~3~CH~2~OH                                                                      Ethanol                                            Ethyl alcohol
  CH~3~CH~2~CH~2~-OH                                                                1-Propanol                                         n-Propyl alcohol
  (CH~3~)~2~CH-OH                                                                   2-Propanol                                         Isopropyl alcohol (Note: Isopropanol would be incorrect. Cannot mix and match between systems.)
                                                                                2-Ethylbutan-1-ol                                  2-Ethylbutanol
                                                                                3-Methyl-3-pentanol
                                                                                2,2-Dimethylcyclopropanol
  Multiple OH functional groups
                                                                                1,2-Ethanediol                                     Ethylene glycol
                                                                                1,1-Ethanediol                                     Acetaldehyde hydrate
                                                                                1,4-Cyclohexanediol
  (form that body fat is stored as)                                                 1,2,3-Propanetriol                                 Glycerol
  ^-^OH can be named as a substituent hydroxyl group (hydroxyalkanes)
                                                                                1,2-Di(hydroxymethyl)cyclohexane
                                                                                2-(hydroxymethyl)-1,3-propanediol
  Find the longest chain of carbons containing the maximum number of ^-^OH groups
                                                                                1-(1-hydroxyethyl)-1-methylcyclopropane
                                                                                2-(1-methylcyclopropyl)ethanol
                                                                                2-(2-hydroxyethyl)-2-methylcyclopropanol
                                                                                3-(2-hydroxyethyl)-3-methyl-1,2-cyclopropanediol

## Acidity

In an O-H bond, the O steals the H\'s electron due to its
electronegativity, and O can carry a negative charge (R-O^-^). This
leads to **deprotonation** in which the nucleus of the H, a proton,
leaves completely. This makes the -OH group (and alcohols) Bronsted
acids. Alcohols are weak acids, even weaker than water. Ethanol has a
pKa of 15.9 compared to water\'s pKa of 15.7. The larger the alcohol
molecule, the weaker an acid it is.

On the other hand, alcohols are also weakly basic. This may seem to be
contradictory\--how can a substance be both an acid and a base? However,
substances exist that can be an acid or a base depending on the
circumstances. Such a compound is said to be amphoteric or amphiprotic.
As a Bronsted base, the oxygen atom in the -OH group can accept a proton
(hydrogen ion.) This results in a positively-charged species known as an
oxonium ion. Oxonium ions have the general formula ROH~2~^+^, where R is
any alkyl group that is a carbon containing species that ranges from
-CH3.

## Alkoxides

When O becomes deprotonated, the result is an **alkoxide**. Alkoxides
are anions. The names of alkoxides are based on the original molecule.
(Ethanol=ethoxide, butanol=butoxide, etc.) Alkoxides are good
nucleophiles due to the negative charge on the oxygen atom.

### Producing an alkoxide

R-OH -\> H^+^ + R-O^-^

In this equation, R-O^-^ is the alkoxide produced and is the conjugate
base of R-OH

Alcohols can be converted into alkoxides by reaction with a strong base
(must be stronger than OH^-^) or reaction with metallic sodium or
potassium. Alkoxides themselves are basic. The larger an alkoxide
molecule is, the more basic it is.

# Reactions

## Conversion of alcohols to haloalkanes

Recall that haloalkanes can be converted to alcohols through
nucleophilic substitution.

+------------------------------------------+
| ```{=html}                               |
| <H2>                                     |
| ```                                      |
| Conversion of a haloalkane to an alcohol |
|                                          |
| ```{=html}                               |
| </H2>                                    |
| ```                                      |
| R-X + OH^-^ → R-OH + X^-^                |
+------------------------------------------+

This reaction proceeds because X (a halogen) is a good leaving group and
OH^-^ is a good nucleophile. OH, however, is a poor leaving group. To
make the reverse reaction proceed, OH must become a good leaving group.
This is done by protonating the OH, turning it into H~2~O^+^, which is a
good leaving group. H^+^ must be present to do this. Therefore, the
compounds that can react with alcohols to form haloalkanes are HBr, HCl,
and HI. Just like the reverse reaction, this process can occur through
S~N~2 (backside attack) or S~N~1 (carbocation intermediate) mechanisms.

+--------------------------------------------------------+
| ```{=html}                                             |
| <H2>                                                   |
| ```                                                    |
| S~N~2 conversion of an alcohol to a haloalkane         |
|                                                        |
| ```{=html}                                             |
| </H2>                                                  |
| ```                                                    |
| R-O-H + H^+^ + X^-^ → R-O^+^-H~2~ + X^-^ → R-X + H~2~O |
+--------------------------------------------------------+

+----------------------------------------------------------------------+
| ```{=html}                                                           |
| <H2>                                                                 |
| ```                                                                  |
| S~N~1 conversion of an alcohol to a haloalkane                       |
|                                                                      |
| ```{=html}                                                           |
| </H2>                                                                |
| ```                                                                  |
| R-O-H + H^+^ + X^-^ → R-O^+^-H~2~ + X^-^ → R^+^ + H~2~O + X^-^ →     |
| R-X + H~2~O                                                          |
+----------------------------------------------------------------------+

As stated in the haloalkane chapter, the two mechanisms look similar but
the mechanism affects the rate of reaction and the stereochemistry of
the product.

## Oxidation of alcohols

Oxidation in organic chemistry always involves either the addition of
oxygen atoms (or other highly electronegative elements like sulphur or
nitrogen) or the removal of hydrogen atoms. Whenever a molecule is
oxidized, another molecule must be reduced. Therefore, these reactions
require a compound that can be reduced. These compounds are usually
inorganic. They are referred to as *oxidizing reagents*.

With regards to alcohol, oxidizing reagents can be strong or weak. Weak
reagents are able to oxidize a primary alcohol group into a aldehyde
group and a secondary alcohol into a ketone. Thus, the R-OH (alcohol)
functional group becomes R=O (carbonyl) after a hydrogen atom is
removed. Strong reagents will further oxidize the aldehyde into a
carboxylic acid (COOH). Tertiary alcohols cannot be oxidized.

An example of a strong oxidizing reagent is chromic acid (H~2~CrO~4~).
Some examples of a weak oxidizing reagents are pyridinium chlorochromate
(PCC) (C~5~H~6~NCrO~3~Cl) and pyridinium dichromate (PDC).

------------------------------------------------------------------------

\<\< Haloalkanes \| Alcohols
\| Alkenes \>\>

id:Kimia Organik/Alkohol


# Organic Chemistry/Ethers

# Ethers

Ethers can be derived from alcohols. The functional group of ethers is
**R-O-R** (instead of R-O-H in an alcohol). Ethers can be viewed as a
water molecule in which both H atoms are replaced with alkyl groups.
Ethers may exist in straight chain carbons (acyclic) or as part of a
carbon ring (cyclic).

!Example ethers. MTBE is acyclic. THF is
cyclic.

# Preparation of ethers

### Synthesis of acyclic ethers

Most acyclic ethers can be prepared using **Williamson\'s synthesis**.
This involves reacting an alkoxide with a haloalkane. As stated
previously, alkoxides are created by reacting an alcohol with metallic
sodium or potassium, or a metal hydride, such as sodium hydride (NaH).
To minimize steric hindrance and achieve a good yield, the haloalkane
must be a primary haloalkane. This is because the mechanism is S~N~2,
where the oxygen atom does a backside attack on the carbon atom with the
halogen atom, causing the halogen atom to leave with its electrons.

### Synthesis of cyclic ethers

You can also use the Williamson synthesis to produce cyclic ethers. You
need a molecule that has a hydroxyl group on one carbon and a halogen
atom attached to another carbon. This molecule will then undergo an
S~N~2 reaction with itself, creating a cyclic ether and a halogen anion.

# Properties of ethers

## Acyclic ethers

### Naming acyclic ethers

Name the two sides of the ether as substituents, then add the word
\"ether\" at the end. For example, CH~3~-O-CH~3~ is dimethyl ether.
CH~3~-O-C(CH~3~)~3~ can be called methyl *tert*-butyl ether (MTBE) or
*tert*-butyl methyl ether (TBME).

### Cleavage of acyclic ethers

Acyclic ethers can be cleaved by a strong acid, typically HI or HBr, but
not HCl. The acid breaks the ether apart into an alcohol and an alkyl
halide (a haloalkane.) Cleavage of ethers by an acid was first seen by
Alexander Butlerov in 1861, when he discovered that hydroiodic acid
causes 2-ethoxypropanoic acid to break apart into iodoethane (ethyl
iodide) and lactic acid (2-hydroxypropanoic acid.) The mechanism used in
acidic cleavage of ethers depends on whether they have primary,
secondary, or tertiary groups attached to oxygen. If one of the carbons
attached to the central oxygen atom is tertiary, benzylic (contains
benzene ring), or allylic (contains carbon-carbon double bond), then the
cleavage will occur via an S~N~1 or an E1 mechanism. The E1 mechanism
leads to an alcohol and an alkene instead of an alkyl halide. These
reactions often take place around 0 degrees C. On the other hand, if
both groups attached to the central oxygen atom are primary or
secondary, the reaction takes place via an S~N~2 mechanism. These
reactions are often conducted at 100 degrees C.

## Cyclic ethers

Two common cyclic ethers are epoxide, which has
two carbons each bonded to the oxygen atom; and
tetrahydrofuran, known by its
abbreviation THF, which has four carbons and an oxygen atom.

### Naming cyclic ethers

### Synthesis of cyclic ethers

### Cleavage of cyclic ethers


# Organic Chemistry/Dienes

\> Dienes

\<\< Alkynes \| Kinds of dienes
\>\>

In alkene chemistry, we
demonstrated that allylic carbon could maintain a cation charge because
the double bond could de-localize to support the charge. What of having
two double bonds separated by a single bond? What of having a compound
that alternates between double bond and single bond? In addition to
other concepts, this chapter will explore what a having a
conjugated system
means in terms of stability and reaction.

Dienes are simply hydrocarbons which contain two double bonds. Dienes
are intermediate between
alkenes and polyenes.

Dienes can divided into three classes:

-   Unconjugated dienes have the double bonds separated by two or more
    single bonds. These are also known as isolated dienes.
-   Conjugated dienes have conjugated double bonds separated by one
    single bond
-   Cumulated dienes (cumulenes) have the
    double bonds sharing a common atom as in a group of compounds called
    *allenes*.

------------------------------------------------------------------------

1.  Kinds of
    dienes
2.  Conjugation
3.  Diene properties and
    reactions

------------------------------------------------------------------------

\<\< Alkynes \| Dienes \|
Aromatics \>\>