Amide formation: draw the structure (or provide the IUPAC name) of the amide formed (appropriate coupling reagent required) between benzoic acid and N-ethyl ethanamine (diethyl amine)
To form an amide between benzoic acid and N-ethyl ethanamine (diethyl amine), you will need an appropriate coupling reagent. In this case, we will use a common coupling reagent called DCC (dicyclohexylcarbodiimide).
Here are the steps to form the amide:
Step 1: Convert benzoic acid to its active ester form.
To do this, react benzoic acid with DCC in the presence of a base such as N,N-dimethylaminopyridine (DMAP). This reaction forms a benzoic acid ester and dicyclohexylurea as a byproduct.
The reaction can be represented as:
Benzoic acid + DCC + DMAP → Benzoic acid ester + Dicyclohexylurea
Step 2: React the formed benzoic acid ester with N-ethyl ethanamine.
Add N-ethyl ethanamine (diethyl amine) to the reaction mixture obtained from Step 1. This reaction forms the amide and cyclohexylurea as a byproduct.
The reaction can be represented as:
Benzoic acid ester + N-ethyl ethanamine → Amide + Cyclohexylurea
The structure of the formed amide between benzoic acid and N-ethyl ethanamine will look like this:
IUPAC name: N-ethyl-N-(phenylcarbonyl)ethanamine
The structure of the amide will have an ethyl group attached to the nitrogen atom and a phenyl group attached to the carbonyl carbon atom of the ethanamine.
To draw the structure of the amide formed between benzoic acid and N-ethyl ethanamine, we need to understand the process of amide formation.
Amide formation typically involves the reaction between a carboxylic acid and an amine. In this case, benzoic acid will react with N-ethyl ethanamine to form the corresponding amide. The reaction requires the use of a coupling reagent, typically a carbodiimide, like N,N'-dicyclohexylcarbodiimide (DCC), to activate the carboxylic acid group and facilitate the formation of the amide bond.
Here are the steps involved in drawing the structure of the amide:
1. Begin with the structure of benzoic acid:
H
|
H - C - C = O
|
C6H5
2. Identify the amine group on N-ethyl ethanamine, which is a diethyl amine. In this case, the ethyl group is attached to the nitrogen atom.
3. Remove the hydroxyl group (-OH) from benzoic acid and replace it with the amine group (-NH2) from N-ethyl ethanamine. This will form the new amide bond.
4. The final structure will have the carbonyl group (C=O) from the carboxylic acid and the amine group (-NH2) from the ethyl amine connected by a new bond.
Therefore, the structure of the amide formed between benzoic acid and N-ethyl ethanamine, using a coupling reagent, would be:
H
|
H - C - C = O
|
C6H5
|
NHCH2CH3
The IUPAC name for this amide is N-ethylbenzamide.