Introduction: Procedure: (Reference: use proper format. Any Changes/Modifications?) Procedure for the Fisher esterification of acetic acid with isoamyl alcohol. Procedural Step Observations/Comments/Inferences Record amounts of reagents used. Table 10.1 Table of Reagents for Experiment 10 Fisher Esterification. Reagent Formula Mwt. (g/mol) d (g/ml) Mp* (C) Bp* (C) Haz. Properties Acetic acid, glacial (conc.) 17.4 M Isoamyl alcohol (3-methyl -1-butanol) 88.15 130 Irritant Sulfuric acid, conc. 18 M H2SO4 1.840 Distilled water H2O 18.02 1.000 0 100 none Diethyl ether 5% sodium carbonate (aq) Na2CO3 (aq) Sat. sodium chloride (aq) (brine) NaCl (aq) Calcium chloride (anhydr) CaCl2 acetone, wash H
Theoretical Yield of Aldol product = % Yield Calculation: Table 4. Infrared Spectrum Data Analysis (see attached spectra) Aldehyde = Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, medium or weak) Functional Group Indicated Functional Group absent: Ketone = Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, medium or weak) Functional Group Indicated Functional Group absent: Aldol Product = Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, medium or weak) Functional Group Indicated Functional Group absent: Discussion: Comments on and give reasons for high or low yield and purity, and sources of error (practical and theoretical), etc.:
Table 17.3.1 shows a summary of the results of the 4-acetamidobenzoic acid synthesis. The calculations for theoretical yield and percent yield are shown below the table. Note: _________________ was the limiting reagent, since the only other reagent involved in the reaction, potassium permanganate was added in excess. Name of Product Mass (g) Appearance of Solid Melting Pt. (C) Theoretical Yield (g) % Yield Theoretical Yield Calculation: % Yield Calculation: Table 17.3.2 Properties of the 4-methylacetanilide Oxidation Product, 4-aminobenzoic acid Table 17.3.2 shows a summary of the results of the 4-aminobenzoic acid synthesis. The calculations for theoretical yield and percent yield are shown below the table. Note: ___________ was the limiting reagent, since the only other reagent involved in the reaction, phosphoric acid, served as a catalyst. Name of Product Mass (g) Appearance of Solid Melting Pt. (C) Yield (g) % Yield Theoretical Yield Calculation: % Yield Calculation:
Region Band # (cm-1) (sharp, broad) (strong, med. or weak) Indicated # H Assignment 1  1.4 6H 2  2.2 3H 3  1H xchanges with D2O Unknown # 360-14-6 Mol. Wt. = 104.15 g/mol Chemical Formula = C8H8 Degrees of Unsaturation = ___________________________________ b.p. = 146C IR Spectra (liquid film (neat) on KBr Disc) 1H-NMR Spectra (at 90 MHz in CDCl3) Infrared Spectra (liquid film (neat) on KBr disc): 1H-NMR Integration Data: (at 90 MHz in CDCl3) Spectrum Region Absorp'n Band # Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  5.2 1H 2  5.7 1H 3  1H 4  7.3 5H Unknown # 360-14-7 Mol. Wt. = 121.18 g/mol Chemical Formula = C8H11N Degrees of Unsaturation = ___________________________________ b.p. = 210C IR Spectra (liquid film (neat) on KBr Disc) 1H-NMR Spectra (at 90 MHz 10.5 mol% in CDCl3) Infrared Spectra (liquid film (neat) on KBr disc): 1H-NMR Integration Data: (at 90 MHz 10.5 mol% in CDCl3) Spectrum Region Absorp'n Band # Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  1.2 3H 2  2.46 2H
Unknown # 360-14-10 Mol. Wt. = 102.13 g/mol Chemical Formula = C5H10O2 Degrees of Unsaturation = ___________________________________ b.p. = 99C IR Spectra (thin film (neat) on KBr Disc) 1H-NMR Spectra (at 400 MHz in CDCl3) Infrared Spectra (thin film (neat) on KBr disc): 1H-NMR Integration Data: (at 400 MHz in CDCl3) Spectrum Region Absorp'n Band # Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  1.1 3H 2  1.3 3H 3  2H 4  4.2 2H Unknown # 360-14-11 Mol. Wt. = 74.1 g/mol Chemical Formula = C4H10O Degrees of Unsaturation = ___________________________________ b.p. = 117.7C IR Spectra (thin film (neat) on KBr Disc) 1H-NMR Spectra (at 90 MHz in CDCl3) Infrared Spectra (thin film (neat) on KBr disc): 1H-NMR Integration Data: (at 90 MHz in CDCl3) Spectrum Region Absorp'n Band # Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  0.9 3H 2  1.4 4H 3  1H xchanges with D2O 4  3.6 2H Unknown # 360-14-12 Mol. Wt. = 136.12 g/mol Chemical Formula = C8H8O2 Degrees of Unsaturation = ___________________________________ b.p. = 230C
Spectrum Region Absorp'n Band# Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  1.2 6H 2  2.9 1H 3 5H Unknown # 360-14-15 Mol. Wt. = 88.12 g/mol Chemical Formula = C4H8O2 Degrees of Unsaturation = ___________________________________ b.p. = 79.9C IR Spectra (liquid film (neat) on KBr Disc) 1H-NMR Spectra (at 90 MHz in CDCl3) Infrared Spectra (neat liquid film on KBr disc): 1H-NMR Integration Data: (at 90 MHz in CDCl3) Spectrum Region Absorp'n Band# Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  1.15 3H 2  2.3 2H 3  3H Unknown # 360-14-16 Mol. Wt. = 124.14 g/mol Chemical Formula = C7H8O2 Degrees of Unsaturation = ___________________________________ m.p. = 55-57C IR Spectra (on KBr Disc) 1H-NMR Spectra (at 90 MHz in CDCl3) Infrared Spectra (on KBr disc): 1H-NMR Integration Data: (at 90 MHz in CDCl3) Spectrum Region Absorp'n Band# Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  3.75 3H
pattern 4  7.5 &8.1 2H 5  10.6 1H xchanges with D2O Unknown # 360-14-19 Mol. Wt. = 59.11 g/mol Chemical Formula = C3H9N Degrees of Unsaturation = ___________________________________ b.p. = 47.8C IR Spectra (liquid film on KBr Disc) 1H-NMR Spectra (at 90 MHz in CDCl3) Infrared Spectra (liquid film on KBr disc): 1H-NMR Integration Data: (at 90 MHz in CDCl3) Spectrum Region Absorp'n Band # Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  0.92 3H 2  1.24 2H xchanges with D2O 3  2H 4  2.65 2H Unknown # 360-14-20 Mol. Wt. = 107.16 g/mol Chemical Formula = C7H9N Degrees of Unsaturation = ___________________________________ b.p. = 200.5C IR Spectra (on KBr Disc) 1H-NMR Spectra (at 400 MHz in CDCl3) Infrared Spectra (on KBr disc): 1H-NMR Integration Data: (at 400 MHz in CDCl3) Spectrum Region Absorp'n Band # Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  2.2 3H 2  3.5 2H xchanges with D2O 3  2H 4  6.95 2H
Unknown # 360-14-21 Mol. Wt. = 138.2 g/mol Chemical Formula = C8H10O2 Degrees of Unsaturation = ___________________________________ b.p. = unknown C IR Spectra (thin film on KBr disc) 1H-NMR Spectra (at 400 MHz in 0.029 g in 0.5 mLCDCl3) Infrared Spectra (on KBr disc): 1H-NMR Integration Data: (at 400 MHz in CDCl3) Spectrum Region Absorp'n Band # Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  2.25 3H 2  3.75 3H 3  1H 4 6.2 3H multiplet Unknown # 360-14-22 Mol. Wt. = 172.2 g/mol Chemical Formula = C8H12O4 Degrees of Unsaturation = ___________________________________ m.p. = 1-2 C
IR Spectra (liquid) 1H-NMR Spectra (at 300 MHz, 10.4 mol% CDCl3) Infrared Spectra (liquid film): 1H-NMR Integration Data: (at 300 MHz in CDCl3) Spectrum Region Absorp'n Band # Frequency (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated Signal # Shift Integrat'n Splitting Comment H Signal Assignment 1  1.32 6H 2 x 3H? 2  4.26 4H 2 x 2H? 3  2H