Carboxylic Acid Derivatives and Their Reactions

Flashcards covering the preparation and reactions of five carboxylic acid derivatives: acid chlorides, acid anhydrides, esters, amides, and nitriles.

What reagent is typically used to prepare acid chlorides from carboxylic acids?

Thionyl chloride (SOCl2) is used to convert carboxylic acids to acid chlorides.

What is the first step in the mechanism for converting carboxylic acids to acid chlorides?

The first step involves converting the OH group into a better leaving group.

What type of reaction occurs when acid chlorides react with water?

Hydrolysis, which produces carboxylic acids.

What is produced when acid chlorides react with alcohols in the presence of pyridine?

Esters are produced when acid chlorides react with alcohols and pyridine.

How can an acid chloride be converted into an amide?

By treating it with an amine.

What is the result of reducing an acid chloride with lithium aluminum hydride?

The acid chloride is reduced to an alcohol.

What type of products are formed when acid chlorides are treated with Grignard reagents?

Alcohols with two alkyl groups are formed from acid chlorides treated with Grignard reagents.

What is a common method for preparing acid anhydrides?

Reacting carboxylic acids with themselves at high temperatures.

What is Fischer esterification?

The process of converting carboxylic acids into esters using an alcohol and an acid catalyst.

How can esters be converted back to carboxylic acids?

By treatment with sodium hydroxide followed by acid (saponification) or through acid-catalyzed hydrolysis.

What happens when you reduce an ester with lithium aluminum hydride?

The ester is reduced to an alcohol.

What reagent is used to convert nitriles to amines?

LiAlH4 (lithium aluminum hydride) can reduce nitriles to amines.

What is the mechanism for the acid-catalyzed hydrolysis of amides?

The amide is protonated, water attacks the carbonyl, and then a leaving group is expelled to yield a carboxylic acid.