Chapter 18: Functional Derivatives of Carboxylic Acids
Table of Contents:
Acidity of Amides, Imides, and Sulfonamides
Under basic conditions, the nucleophile attacks the carbonyl carbon pushing electrons up to the oxygen. Under acidic conditions, oxygen first gets protonated which is followed by the nucleophile attack.
Reactions With Water: Hydrolysis
Acid Chloride or Anhydride with H2O = Carboxylic Acid
Hydrolysis of Esters
Esters can be converted into carboxylic acids under acidic or basic conditions.
Hydrolysis of Amides
Hydrolysis of Nitriles
Reactions With Alcohols
Acid Chloride or Anhydride with Alcohol = Ester
Note: Amides do NOT react with alcohols.
Reactions With Ammonia and Amines
Acid Chloride or Anhydride or Ester with an Amine = Amide
Note: Amides do NOT react with amines.
Reaction of Acid Chlorides with Salts of Carboxylic Acids
Reactions With Organometallic Reagents
Grignard and organolithium reagents react twice with esters or acid chlorides to give tertiary alcohols.
Ester with Grignard Reagent Mechanism
How to predict the reactants from the product of Ester with Grignard?
If you see the product is a tertiary alcohol with two identical R groups, then it could've come from the reaction of ester or acid chloride with Grignard reagent or organolithium.
To go back:
Break the bonds between COH and two R groups attached to it.
Turn OH into =O and add MgBr or Li to the carbons broken off. Second step is acid/water.
Reaction of Acid Chlorides with Gilman Reagent (organocuprate)
Reduction of Acid Chloride, Esters and Carboxylic Acids with LiAlH4
Lithium aluminum hydride can be used to reduce esters, acid chlorides and carboxylic acids to alcohols.
Mechanism of Ester with LiAlH4
Reduction of Amides with LiAlH4
Lithium aluminum hydride can be used to reduce amides to amines.
Reduction of Nitrile with LiAlH4
Lithium aluminum hydride can be used to reduce nitriles (CN) into amines (CH2NH2).
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