Organic Chemistry -Amides, Esters, and
Anhydrides
Test Study Guide: -Reactivity Principles
Ch.9 Carboxylic Acid -Nucleophilic Acyl
Substitution Reactions
Derivatives -And More
CONCEPT SUMMARY
Amides, Esters, and Anhydrides: Aesthetic Points
Amides
Formed through the condensation of carboxylic acids with ammonia or amines.
Named with the suffix -amide.
Substituted amides have alkyl groups prefixed with N- at the beginning of their names.
Cyclic amides are referred to as lactams, named using Greek letters corresponding to the carbon that bonds
with nitrogen (e.g., 9-lactam, γ-lactam).
Esters
Result from the condensation of carboxylic acids and alcohols via Fischer esterification.
Designated with the suffix -oate.
The esterifying group is indicated as a substituent without a numerical designation.
Cyclic esters are known as lactones, named based on the number of carbons in the ring and the Greek letter
for the carbon that bonds with oxygen (e.g., α-acetolactone, β-propiolactone).
Triacylglycerols and Saponification
Triacylglycerols are a form of fat storage, consisting of three ester bonds formed between glycerol and fatty
acids.
Saponification is the chemical process that breaks down fats using a strong base to produce soap, which
consists of salts derived from long-chain carboxylic acids.
Anhydrides
Anhydrides are formed through the condensation of two carboxylic acids, resulting in dimers.
Symmetric anhydrides are named after the parent carboxylic acid with “anhydride” appended. Asymmetric
anhydrides are named by listing the parent carboxylic acids in alphabetical order followed by “anhydride.”
Cyclic anhydrides can be synthesized by heating dioic acids, with five- or six-membered rings being particularly
stable.
Reactivity Principles
In nucleophilic substitution reactions, the reactivity hierarchy is as follows: anhydrides > esters > amides.
Steric hindrance occurs when substituents crowd the reactive site, potentially slowing or preventing reactions.
Protecting groups like acetals can be employed to enhance steric hindrance or reduce reactivity in specific
molecular regions.
Induction
Anhydrides
Test Study Guide: -Reactivity Principles
Ch.9 Carboxylic Acid -Nucleophilic Acyl
Substitution Reactions
Derivatives -And More
CONCEPT SUMMARY
Amides, Esters, and Anhydrides: Aesthetic Points
Amides
Formed through the condensation of carboxylic acids with ammonia or amines.
Named with the suffix -amide.
Substituted amides have alkyl groups prefixed with N- at the beginning of their names.
Cyclic amides are referred to as lactams, named using Greek letters corresponding to the carbon that bonds
with nitrogen (e.g., 9-lactam, γ-lactam).
Esters
Result from the condensation of carboxylic acids and alcohols via Fischer esterification.
Designated with the suffix -oate.
The esterifying group is indicated as a substituent without a numerical designation.
Cyclic esters are known as lactones, named based on the number of carbons in the ring and the Greek letter
for the carbon that bonds with oxygen (e.g., α-acetolactone, β-propiolactone).
Triacylglycerols and Saponification
Triacylglycerols are a form of fat storage, consisting of three ester bonds formed between glycerol and fatty
acids.
Saponification is the chemical process that breaks down fats using a strong base to produce soap, which
consists of salts derived from long-chain carboxylic acids.
Anhydrides
Anhydrides are formed through the condensation of two carboxylic acids, resulting in dimers.
Symmetric anhydrides are named after the parent carboxylic acid with “anhydride” appended. Asymmetric
anhydrides are named by listing the parent carboxylic acids in alphabetical order followed by “anhydride.”
Cyclic anhydrides can be synthesized by heating dioic acids, with five- or six-membered rings being particularly
stable.
Reactivity Principles
In nucleophilic substitution reactions, the reactivity hierarchy is as follows: anhydrides > esters > amides.
Steric hindrance occurs when substituents crowd the reactive site, potentially slowing or preventing reactions.
Protecting groups like acetals can be employed to enhance steric hindrance or reduce reactivity in specific
molecular regions.
Induction
