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Chapter 18: Problem 19

What is an amide bond? Show an amide bond between dimethylamine and acetic acid chloride.

Short Answer

Expert verified
An amide bond is a functional group consisting of a carbonyl group (C=O) bonded to a nitrogen atom (N), with a general structure of \(-RC(O)NR_2\). The reaction between dimethylamine (\(CH_3NHCH_3\)) and acetic acid chloride (\(CH_3COCl\)) forms an amide bond, resulting in the product N,N-dimethylacetamide (\(CH_3C(O)N(CH_3)_2\)).

Step by step solution

01

Definition of an Amide Bond

An amide bond is a functional group consisting of a carbonyl group (C=O) that is bonded to a nitrogen atom (N). The general structure of an amide bond is \(-RC(O)NR_2\), where R and R2 can be hydrogen atoms or alkyl/aryl groups.
02

Reactants

In this case, we have two reactants: dimethylamine and acetic acid chloride. 1. Dimethylamine is a secondary amine with the formula \(CH_3NHCH_3\). The nitrogen atom in dimethylamine has two methyl groups attached to it. 2. Acetic acid chloride, or acetyl chloride, is an acyl chloride with the formula \(CH_3COCl\). It consists of a carbonyl group (C=O) and a chlorine atom attached to the same carbon atom.
03

Formation of Amide Bond

An amide bond forms when the nitrogen atom of an amine reacts with the carbonyl carbon of an acyl chloride. The reaction proceeds with the amine acting as a nucleophile, attacking the carbonyl carbon atom and displacing the chloride ion (Cl-) in the process.
04

Product

The reaction of dimethylamine with acetic acid chloride will produce N,N-dimethylacetamide, an amide, and a chloride ion. The structure of the product can be represented as \[CH_3C(O)N(CH_3)_2\]. In this molecule, the amide bond is between the carbonyl carbon and the nitrogen atom.
05

Summary

An amide bond is a functional group consisting of a carbonyl group bonded to a nitrogen atom. The reaction between dimethylamine (\(CH_3NHCH_3\)) and acetic acid chloride (\(CH_3COCl\)) forms an amide bond, resulting in the product N,N-dimethylacetamide (\(CH_3C(O)N(CH_3)_2\)).

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