Amides and Nitriles: Reactions
Start with the big picture
Amide nitrogen donates electron density into the carbonyl, reducing the carbonyl carbon’s electrophilicity and making amides relatively unreactive in nucleophilic acyl substitution. Nitriles contain a polarized C≡N bond, with an electrophilic carbon and a nucleophilic nitrogen. Their transformations include hydrolysis and reduction; nitriles also react with organometallic reagents to form ketones after hydrolysis. Amides can be made from activated acyl compounds or through coupling, and can undergo hydrolysis, rearrangement, dehydration, or reduction. The topic connects these reactions to functional-group identification, including characteristic IR absorptions, and compares boiling points and relative reactivity across acyl derivatives.
What you'll learn
- Relate amide resonance to reduced carbonyl electrophilicity and acyl-substitution reactivity.
- Compare the structure, polarity, and physical properties of amides and nitriles.
- Identify common synthetic routes to amides and nitriles.
- Summarize major hydrolysis, reduction, rearrangement, and addition reactions of these groups.
- Recognize the listed IR features used to identify amides and nitriles.
Continue your study
Work through the complete notes and reinforce the topic with the study tools available in the full lesson.
