what is the name of the general reaction type that carboxylic acids, esters, and amides underg
Nucleophilic acyl addition
Electrophilic acyl substitution
Nucleophilic acyl substitution
Electrophilic acyl addition
The correct answer and explanation is :
The correct answer is Nucleophilic acyl substitution.
Explanation:
Nucleophilic acyl substitution is the general reaction type that occurs with carboxylic acids, esters, and amides. This reaction involves the substitution of an acyl group (R-C=O) with a nucleophile, typically a compound with a lone pair of electrons that attacks the electrophilic carbonyl carbon (C=O) of the acyl group.
In these types of reactions, the carbonyl carbon is electrophilic due to the partial positive charge developed by the polar nature of the C=O bond. This makes the carbonyl carbon susceptible to attack by a nucleophile. The nucleophile (such as alcohols, amines, or water) replaces the leaving group (such as hydroxide or halide) attached to the carbonyl carbon.
Here’s how it works in each case:
- Carboxylic Acids: Carboxylic acids undergo nucleophilic acyl substitution when they react with nucleophiles like alcohols or amines. For example, when a carboxylic acid reacts with an alcohol, an ester is formed in a process known as esterification.
- Esters: Esters are also subject to nucleophilic acyl substitution. In ester hydrolysis, for example, water acts as a nucleophile and breaks the ester bond to produce a carboxylic acid and alcohol.
- Amides: Amides undergo nucleophilic acyl substitution as well. Amides are less reactive compared to carboxylic acids or esters, but they can be hydrolyzed under acidic or basic conditions, leading to the formation of carboxylic acids and amines.
In nucleophilic acyl substitution, the mechanism typically involves the following steps:
- The nucleophile attacks the electrophilic carbonyl carbon.
- A tetrahedral intermediate is formed.
- The leaving group departs, leading to the formation of the new product.
This reaction type is widely applicable in organic chemistry, particularly in the synthesis of esters, amides, and other acyl derivatives.
