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Chapter 20: Q14P (page 672)

How would you prepare 1-phenyl-2-butanone, C6H5CH2COCH2CH3, from

benzyl bromide,C6H5CH2Br? More than one step is required.

Short Answer

Expert verified

The preparation of 1-phenyl-2-butanone from benzyl bromide is shown in two step as

follows:

Step by step solution

01

Conversion of benzyl bromide into benzylnitrile.

The given starting material, benzyl bromide is attacked by a nucleophile

cyanide,CN-via a second order nucleophilic substitution pathway. This leads

to the formation of benzylnitrile as shown below.

02

Conversion of benzylnitrile into 1-phenyl-2-butanone.

Benzylnitrile obtained in the first step is reacted with ethylmagnesium bromide gives

the imine salt which is further acidified with aqueous acid to produce 1-phenyl-2-

butanone as the final product.

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Most popular questions from this chapter

How could you convert butanenitrile into the following compounds?

Write each step showing the reagents needed.

(a) 1-Butanol

(b) Butylamine

(c) 2-Methyl-3-hexanone

Arrange the compounds in each of the following sets in order of increasing basicity:

(a) Magnesium acetate, magnesium hydroxide, methyl magnesium bromide

(b) Sodium benzoate, sodium p-nitrobenzoate, sodium acetylide

(c) Lithium hydroxide, lithium ethoxide, lithium formate

How would you prepare the following carboxylic acids?

(a)(CH3)3CCO2Hfrom(CH3)3CCI

(b) CH3CH2CH2CO2HfromCH3CH2CH2Br

2-Bromo-6, 6-dimethylcyclohexanone gives 2, 2-dimethylcyclopentane-carboxylic acid on treatment with aqueous NaOH followed by acidification, a process called the Favorskii reaction. Propose a mechanism.

Nitriles can be converted directly to esters by the Pinner reaction, which first produces an iminoester salt that is isolated and then treated with water to give the final product. Propose a mechanism for the Pinner reaction using curved arrows to show the flow of electrons at each step.
See all solutions

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