Chapter 20, Problem 20.65P

Interpretation Introduction

(a)

Interpretation:

A synthesis of the given compound by using acetyl chloride is to be determined.

Concept introduction:

Sodium benzoate is the salt of conjugate base or sodium salt of benzoic acid. When acyl halide reacts with sodium benzoate, it gives the ester. Sodium benzoate acts as the nucleophile. Nucleophile is the negatively charged ion attacks the carbonyl carbon and expels the good leaving group.

Answer to Problem 20.65P

The way of synthesis of the given compound by using acetyl chloride is as follows:

Explanation of Solution

The way of synthesis of the given compound by using acetyl chloride is as follows:

Sodium benzoate is a sodium salt of benzoic acid. When acyl halide reacts with sodium benzoate, it gives the ester. Sodium benzoate, as s nucleophile, is used to undergo nucleophilic addition- elimination reaction with acid chloride. Benzoate’s negatively charged ion attacks the carbonyl carbon of acetyl chloride and expels the good leaving group chlorine.

Conclusion

From the structure of the given reactant and product, structure of the reagent is determined.

Interpretation Introduction

(b)

Interpretation:

A synthesis of the given compound by using the acetyl chloride is to be determined.

Concept introduction:

Sodium phenoxide is produced by sodium hydroxide and Phenol. Ester can be prepared by treating acetyl chloride with phenoxide. Sodium phenoxide is a moderately strong base.

Answer to Problem 20.65P

The way of synthesis of the given compound by using acetyl chloride is as follows:

Explanation of Solution

The way of synthesis of the given compound by using acetyl chloride is as follows:

Ester can be prepared by treating acetyl chloride with sodium phenoxide. Sodium phenoxide, as a nucleophile, is used to undergo nucleophilic addition- elimination reaction with acid chloride. Phenoxide, the negatively charged ion attacks the carbonyl carbon of acetyl chloride and expels the good leaving group chlorine and forms ester.

Conclusion

From the structure of given reactant and product, structure of reagent is determined.

Interpretation Introduction

(c)

Interpretation:

A synthesis of the given compound by using acetyl chloride is to be determined.

Concept introduction:

${\text{LiAlH}}_{\text{4}}$ is the reducing agent, a source of hydride ion, ${\text{H}}^{\text{-}}$. Hydride ion is a very strong base and a moderately good nucleophile. It attacks and adds to the electrophilic carbon of a carbonyl group, reducing it. This is usually followed by acid workup which reduces the oxygen to OH. The overall reaction converts a carbonyl group to an alcohol.

It converts the acid chloride or anhydrides to primary alcohol. It’s also used for reduction of carbonyl compound to corresponding alcohol, and after removing the hydrogen from alcohol, it gives alkoxide. Alkoxide ion attacks the carbonyl carbon of the acid chloride and expels the good leaving group and forms the ester as product.

Answer to Problem 20.65P

The way of synthesis of the given compound by using acetyl chloride is as follows:

Explanation of Solution

The way of synthesis of the given compound by using acetyl chloride is as follows:

Acetyl halide is converted to alkoxide by treating it with ${\text{LiAlH}}_{\text{4}}$. Then, in the presence of benzoyl chloride, it is converted to the required product i.e. ester. Alkoxide acts as nucleophile and undergoes nucleophilic addition- elimination reaction with acid chloride. Alkoxide ion attacks the carbonyl carbon of the acid chloride, expels the good leaving group and forms the ester as product.

Conclusion

From the structure of the given reactant and product, structure of reagent is determined.

Interpretation Introduction

(d)

Interpretation:

A synthesis of the given compound by using acetyl chloride is to be determined.

Concept introduction:

${\text{LiAlH}}_{\text{4}}$ is the reducing agent, a source of hydride ion, ${\text{H}}^{\text{-}}$. The hydride ion is a very strong base and a moderately good nucleophile. It attacks and adds to the electrophilic carbon of a carbonyl group, reducing it. This is usually followed by acid workup which reduces the oxygen to OH. The overall reaction converts a carbonyl group to an alcohol.

It is also used for reduction of amides to corresponding amines.

Answer to Problem 20.65P

The way of synthesis of given compound by using acetyl chloride is as follows:

Explanation of Solution

The way of synthesis of given compound by using acetyl chloride is as follows:

In the first step, acid chloride converts to amide in the presence of organolithium amine reagent. Amide is reduced with ${\text{LiAlH}}_{\text{4}}$ to form the required compound i.e. amine.

Conclusion

From the structure of given reactant and product, structure of reagent is determined.

Interpretation Introduction

(e)

Interpretation:

A synthesis of given compound by using the acetyl chloride is to be determined.

Concept introduction:

${\text{LiAlH}}_{\text{4}}$ is the reducing agent, a source of hydride ion, ${\text{H}}^{\text{-}}$. The hydride ion is a very strong base and a moderately good nucleophile. It attacks and adds to the electrophilic carbon of a carbonyl group, reducing it. This is usually followed by acid workup which reduces the oxygen to OH. The overall reaction converts a carbonyl group to an alcohol.

It converts the acid chloride or anhydrides to primary alcohol. It’s also used for reduction of carbonyl a compound to corresponding alcohol. And after remove the hydrogen from alcohol to get alkoxide. Alkoxide ion attacks the carbonyl carbon of the acid chloride and expels the good leaving group and form the ester as product. Alcohol is reacting with strong acid at required temperature to get the ester.

Answer to Problem 20.65P

The way of synthesis of given compound by using acetyl chloride is as follows:

Explanation of Solution

The way of synthesis of given compound by using acetyl chloride is as follows:

In the first step, acetyl chloride is converted to aldehyde and then alcohol by treating with ${\text{LiAlH}}_{\text{4}}$ followed by water treatment. In second step, alcohol converts to ether in presence of sulfuric acid and heat.

Conclusion

From the structure of given reactant and product, structure of reagent is determined.

Interpretation Introduction

(f)

Interpretation:

A synthesis of given compound by using acetyl chloride is to be determined.

Concept introduction:

The reagent $\text{LiAl}{\left(\text{Ot-Bu}\right)}_{\text{3}}\text{H}$ is a reducing reagent. It is a more controlled reagent than ${\text{LiAlBH}}_{\text{4}}$ because it only has one hydride to give and not reduce everything in sight.

Answer to Problem 20.65P

The way of synthesis of given compound by using acetyl chloride is as follows:

Explanation of Solution

The way of synthesis of given compound by using acetyl chloride is as follows:

When acyl chloride react with $\text{LiAl}{\left(\text{Ot-Bu}\right)}_{\text{3}}\text{H}$, it forms acetaldehyde. Carbonyl carbon of acyl halide breaks the $\text{C-O}$$\text{π}$ bond by adding hydride from $\text{Al-H }$ and forms an intermediate. After expelling the chloride ion, the negatively charged oxygen comes down and reforms the $\text{C-O}$$\text{π}$ bond to form an aldehyde.

Conclusion

From the structure of given reactant and product, structure of reagent is determined.

Interpretation Introduction

(g)

Interpretation:

A synthesis of given compound by using acetyl chloride is to be determined.

Concept introduction:

Acid chloride reacts with Gilmann reagent to give the ketone.

Answer to Problem 20.65P

The way of synthesis of given compound by using acetyl chloride is as follows:

Explanation of Solution

The way of synthesis of given compound by using acetyl chloride is as follows:

Acetyl chloride is converted to ketone in the presence lithium dimethylcuprate. Ketone does not undergo nucleophilic attack by Gilmann reagent as the reagent is a soft nucleophile.

Conclusion

From the structure of given reactant and product, structure of reagent is determined.

Interpretation Introduction

(h)

Interpretation:

A synthesis of given compound by using the acetyl chloride is to be determined.

Concept introduction:

Acid chloride is converted to ester in presence of sodium alkoxide. Alkoxide ion attacks the carbonyl carbon of acid chloride and expels the good leaving group forming ester as the product.

Answer to Problem 20.65P

The way of synthesis of given compound by using acetyl chloride is as follows:

Explanation of Solution

The way of synthesis of given compound by using acetyl chloride is as follows:

Acetyl chloride is converted to ester in presence of sodium ethoxide. Ethoxide ion attacks the carbonyl carbon of acid chloride and expels the good leaving group, forming the ester as a product.

Conclusion

From the structure of given reactant and product, structure of reagent is determined.