Chapter 18, Problem 18.32P

(a)

Interpretation Introduction

Interpretation:

Product of treating $\gamma$-butyrolactone with the given reagent has to be shown.

Concept introduction:

Reaction of an ester with ammonia or an amine:

Treatment of an ester with ammonia or a primary or secondary amine gives an amide.

The nucleophilic addition of the ammonia or amine to the carbonyl carbon occurs followed by a proton transfer and a tetrahedral addition intermediate is formed. The intermediate can directly alkoxide and lose a proton to the alkoxide to give products.

(b)

Interpretation Introduction

Interpretation:

Product of treating $\gamma$-butyrolactone with the given reagent has to be shown.

Concept introduction:

$LiAl{H}_4$- Lithium Aluminium hydride:

• The reduction using $LiAl{H}_4$ are carried out in diethyl ether or tetrahydrofuran (THF)
• It reduces ketones to secondary alcohols
• It reduces aldehydes to primary alcohols
• It reduces carboxylic acids and esters to primary alcohols

(c)

Interpretation Introduction

Interpretation:

Product of treating $\gamma$-butyrolactone with the given reagent has to be shown.

Concept introduction:

Alkyl or aryl magnesium halides (RMgX) are known as Grignard reagent. The Grignard reaction is an organometallic chemical reaction in which the Grignard reagent act as nucleophile and attack electrophilic carbon atom that are present within polar bonds to yield a carbon-carbon bond

Reaction of Grignard reagent with a formic ester followed by hydrolysis in aqueous acid yields secondary alcohol. Tertiary alcohol can be prepared by the reaction of Grignard reagent with ester other than formate.

(d)

Interpretation Introduction

Interpretation:

Product of treating $\gamma$-butyrolactone with the given reagent has to be shown.

Concept introduction:

Ester Hydrolysis: Ester hydrolysis can be caused by acid and base.

Saponification: Ester hydrolysis taking place in presence of base such as $NaOH$ or $KOH$ is known as saponification. Ester reacts with hydroxide ion forming carboxylic acid which again reacts with base resulting in the formation of a caboxylate anion.

(e)

Interpretation Introduction

Interpretation:

Product of treating $\gamma$-butyrolactone with the given reagent has to be shown.

Concept introduction:

Alkyl lithium:

It is an important reagent in organic synthesis which contain carbon-lithium bonds. The reagent is used to transfer the organic group to the substrates in different steps through nucleophilic addition or deprotonation.

(f)

Interpretation Introduction

Interpretation:

Product of treating $\gamma$-butyrolactone with the given reagent has to be shown.

Concept introduction:

DIBALH:

The reagent is an organoaluminium reagent which converts esters to aldehydes.