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Chapter 22: Problem 58

Draw a structural formula for each of the following. a. 3-methylpentanoic acid b. ethyl methanoate c. methyl benzoate d. 3 -chloro- 2,4 -dimethylhexanoic acid

Short Answer

Expert verified
a. H3C-CH2-CH(-CH3)-CH2-CO2H b. H3C-CH2-O-CO-CH3 c. C6H5-CO2-CH3 d. H3C-CH(-CH3)-CH(-Cl)-CH(-CH3)-CH2-CO2H

Step by step solution

01

Identify main chain and functional group

Pentanoic acid indicates there is a 5-carbon chain with a carboxylic acid functional group. The prefix "3-methyl" indicates that there is a methyl group on the 3rd carbon atom in the chain.
02

Draw the structure

Starting with the terminal carbon, we have the carboxylic acid functional group. From there, we draw the rest of the carbon chain, adding the methyl group on the 3rd carbon atom: H3C-CH2-CH(-CH3)-CH2-CO2H b. ethyl methanoate
03

Identify main groups

Methanoate (an ester) indicates there is a methanol group connected to a carbonyl. "Ethyl" indicates there's an ethyl group connected to the carbonyl group.
04

Draw the structure

We draw the methanoate functional group with the carbonyl and connect the ethyl group to the carbonyl: H3C-CH2-O-CO-CH3 c. methyl benzoate
05

Identify main groups:

Benzoate (an ester) indicates there is a benzene ring connected to a carbonyl group. "Methyl" indicates there's a methyl group connected to the carbonyl group.
06

Draw the structure

Draw the benzene ring with the carbonyl group and attach the methyl group to the carbonyl group: C6H5-CO2-CH3 d. 3-chloro-2,4-dimethylhexanoic acid
07

Identify main chain and functional groups

Hexanoic acid indicates there is a 6-carbon chain with a carboxylic acid functional group. The prefix "3-chloro-2,4-dimethyl" indicates that there is a chlorine atom on the 3rd carbon atom in the chain and methyl groups on the 2nd and 4th carbon atoms.
08

Draw the structure

Starting with the terminal carbon, we have the carboxylic acid functional group. From there, we draw the rest of the carbon chain, adding the methyl and chloro groups in the specified positions: H3C-CH(-CH3)-CH(-Cl)-CH(-CH3)-CH2-CO2H

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