Nucleophilic Acyl Substitution Reactions Strongly polarized acyl groups make the C=O carbon atom more electrophilic OR SR t-a R Amide Ester Thioester Acid anhydride Acid chloride Reactivity Cengage Learring All Fights Reoorved
▪ Strongly polarized acyl groups make the C=O carbon atom more electrophilic Nucleophilic Acyl Substitution Reactions
Nucleophilic Acyl Substitution Reactions Usually possible to convert more More reactive reactive acid derivatives to less Acid halide reactive ones Acid halides and Acid anhydride acid anhydrides do not persist in living R SR organisms because Thioester they react rapidly with water Ester NH2 Less reactive Amide
Usually possible to convert more reactive acid derivatives to less reactive ones ▪ Acid halides and acid anhydrides do not persist in living organisms because they react rapidly with water Nucleophilic Acyl Substitution Reactions
Nucleophilic Acyl Substitution Reactions Five common reactions for carboxylic acid derivatives Hydrolysis Reaction with water to yield carboxylic acid Alcoholysis Reaction with alcohol to yield ester Aminolysis 。 Reaction with ammonia or amine to yield amide Reduction Reaction with hydride reducing agent to yield aldehyde or alcohol Grignard reaction Reaction with organomagnesium reagent to yield alcohol
Five common reactions for carboxylic acid derivatives ▪ Hydrolysis ▪ Reaction with water to yield carboxylic acid ▪ Alcoholysis ▪ Reaction with alcohol to yield ester ▪ Aminolysis ▪ Reaction with ammonia or amine to yield amide ▪ Reduction ▪ Reaction with hydride reducing agent to yield aldehyde or alcohol ▪ Grignard reaction ▪ Reaction with organomagnesium reagent to yield alcohol Nucleophilic Acyl Substitution Reactions
Nucleophilic Acyl Substitution Reactions 0 R OR' R -NH2 R R OH Alcoholysis Aminolysis Reduction ← R'OH NH3 (H 0 0 H20 R'MgX R'MgX R OH R Hydrolysis Acid Grignard reaction derivative Congage Learing All Rights Reserved
Nucleophilic Acyl Substitution Reactions
Worked Example 16.1 Predicting the Product of a Nucleophilic Acyl Substitution Reaction Predict the product of the following nucleophilic acyl substitution reaction of benzoyl chloride with propan-2-ol OH CH3CHCH3 Benzoyl chloride
Predict the product of the following nucleophilic acyl substitution reaction of benzoyl chloride with propan-2-ol Worked Example 16.1 Predicting the Product of a Nucleophilic Acyl Substitution Reaction