Chapter 3: Problem 60
Which of the following will most easily react with an amine to form an amide? A. acyl chloride B. ester C. carboxylic acid D. acid anhydride
Short Answer
Expert verified
Acyl chloride
Step by step solution
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Carboxylic Acid Derivatives
Carboxylic acid derivatives are compounds that can be hydrolyzed to carboxylic acids. They include a variety of functional groups that differ mainly by the nature of the leaving group. The major derivatives are:
The reactivity mainly depends on how easily the leaving group can depart. Now, let's dive into each derivative's specifics and their reactivity.
- Acyl chlorides
- Esters
- Amides
- Anhydrides
The reactivity mainly depends on how easily the leaving group can depart. Now, let's dive into each derivative's specifics and their reactivity.
Amine Reactivity
Amines are nucleophiles, meaning they donate a pair of electrons to form a new bond. In reactions with carboxylic acid derivatives, amines attack the carbonyl carbon because it is electrophilic.
The reactivity of amines depends on the type of carboxylic acid derivative they are reacting with. Acyl chlorides react readily with amines due to the excellent leaving group, chloride ion.
When an amine reacts with an acyl chloride, an amide is formed almost instantly.
However, when reacting with less reactive derivatives like esters or carboxylic acids, the reaction is slower because these compounds have poorer leaving groups.
The reactivity of amines depends on the type of carboxylic acid derivative they are reacting with. Acyl chlorides react readily with amines due to the excellent leaving group, chloride ion.
When an amine reacts with an acyl chloride, an amide is formed almost instantly.
However, when reacting with less reactive derivatives like esters or carboxylic acids, the reaction is slower because these compounds have poorer leaving groups.
Acyl Chloride Reactivity
Acyl chlorides are among the most reactive carboxylic acid derivatives. This is because the chloride ion is a very good leaving group. When amines react with acyl chlorides, the result is the rapid formation of an amide.
The reaction mechanism involves the nucleophilic attack by the amine on the carbonyl carbon of the acyl chloride, followed by the departure of the chloride ion.
The overall process is straightforward and efficient. This is why acyl chlorides are often used as reactants in laboratories when the goal is to synthesize an amide.
Other carboxylic acid derivatives like esters, carboxylic acids, and anhydrides cannot match the reactivity of acyl chlorides due to their inferior leaving groups, making the reaction process slower and less efficient.
The reaction mechanism involves the nucleophilic attack by the amine on the carbonyl carbon of the acyl chloride, followed by the departure of the chloride ion.
The overall process is straightforward and efficient. This is why acyl chlorides are often used as reactants in laboratories when the goal is to synthesize an amide.
Other carboxylic acid derivatives like esters, carboxylic acids, and anhydrides cannot match the reactivity of acyl chlorides due to their inferior leaving groups, making the reaction process slower and less efficient.
