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Describe the differences between the nucleophilic substitution of different amides.

The nucleophilic substitution of amides varies depending on the type of amide and the reaction conditions.

Primary amides, which have an NH2 group attached to the carbonyl carbon, undergo nucleophilic substitution more readily than secondary or tertiary amides. This is because the nitrogen lone pair in primary amides is more available for attack by a nucleophile.

Secondary and tertiary amides, which have alkyl or aryl groups attached to the nitrogen, are less reactive towards nucleophilic substitution. This is due to steric hindrance, which makes it more difficult for a nucleophile to approach the carbonyl carbon.

The reaction conditions also play a role in the nucleophilic substitution of amides. For example, using a strong nucleophile and a polar aprotic solvent can increase the rate of substitution for all types of amides. Additionally, using acidic conditions can hydrolyze the amide bond, leading to the formation of a carboxylic acid and an amine.

In summary, the reactivity of amides towards nucleophilic substitution depends on the type of amide and the reaction conditions. Primary amides are more reactive than secondary and tertiary amides, and using strong nucleophiles and polar aprotic solvents can increase the rate of substitution. Acidic conditions can also hydrolyze the amide bond.

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