Wize University Organic Chemistry Textbook > Carboxylic Acid Derivatives (Nucleophilic Acyl Substitutions)
Carboxylic Acid Derivatives
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Nomenclature and Physical Properties
Carboxylic acid derivatives are shown below. They all differ based on their "R" groups.
- acid chlorides (left) have the suffix -oyl chloride
- acid anhydrides (second) have the suffix -anhydride
- esters (third) have the suffix - oate
- amides (right) have the suffix - amide
- amides have hydrogen bond donors and hydrogen bond acceptors
- other carboxylic acid derivatives experience dipole-dipole interactions
Important Resonance Structure in Amides
Amides have a major resonance structure that changes the hybridization of the nitrogen atom from sp3 to sp2. This also gives double bond character to the carbon-nitrogen bond and makes amides especially stable.
Watch Out!
Beware the hybridization of the nitrogen atom in an amide! It is sp2 due to the this resonance structure.