He is buying 16 pounds of chicken and half that amount in hamburgers so he's buying 16/2 = <<16/2=8>>8 pounds of hamburgers
He's going to buy 2 more pounds of hotdogs than hamburgers, which are 8 pounds so he'll have 2+8 = <<2+8=10>>10 pounds of hot dogs
He's going to buy sides that weigh half the amount of the hot dogs so that's 10/2 = <<10/2=5>>5 pounds of sides
He's buying 16 pounds of chicken, 8 pounds of hamburgers, 10 pounds of hot dogs and 5 pounds of sides for a total of 16+8+10+5 = <<16+8+10+5=39>>39 pounds of food
#### 39