Draw the organic product formed when the following compounds...

Name: Problem 67, Chapter 15: CHEMISTRY: The Molecular Nature of Matter and Change
Uploaded: 2020-07-09T20:29:55-08:00
Duration: 2 min 26 s
Channel: Dalton Hilovsky
Description: Draw the organic product formed when the following compounds undergo a substitution reaction: (a) acetic acid and methylamine; (b) butanoic acid and 2 -propanol; (c) formic acid and 2 -methyl- 1 -propanol.

Draw the organic product formed when the following compounds undergo a substitution reaction: (a) acetic acid and methylamine; (b) butanoic acid and 2 -propanol; (c) formic acid and 2 -methyl- 1 -propanol.

Key Concepts

Nucleophilic Acyl Substitution

This is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks the electrophilic carbon of a carboxylic acid derivative (such as a carboxylic acid, ester, or acid chloride). The attack leads to a tetrahedral intermediate, which then ejects a leaving group and reforms the carbonyl, substituting the original group with the nucleophile. This mechanism is the basis for many transformations including the formation of amides and esters.

Amide Formation

Amide formation typically involves the reaction of a carboxylic acid with an amine, resulting in the substitution of the hydroxyl group with an amine group. Although direct condensation usually gives a salt, under appropriate conditions (or with a dehydrating agent), water is removed to yield an amide. This process is an example of nucleophilic acyl substitution where the amine acts as the nucleophile attacking the carbonyl carbon.

Esterification Reaction

Esterification is the process by which a carboxylic acid reacts with an alcohol to form an ester and water. This reaction often involves acid catalysis to increase the electrophilicity of the carbonyl carbon, enabling the alcohol (acting as a nucleophile) to attack. The mechanism proceeds via a tetrahedral intermediate and involves the elimination of water, exemplifying nucleophilic acyl substitution in the formation of esters.

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