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Chapter 20: Q14E (page 653)

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 benzyl nitrile.

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 benzyl nitrile as shown below.

02

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

Benzyl nitrile obtained in the first step is reacted with ethyl magnesium 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 would you prepare the following carboxylic acids?

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

(b) CH3CH2CH2CO2HfromCH3CH2CH2Br

Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occursby initial protonation of the nitrogen atom, followed by nucleophilicaddition of water. Review the mechanism of base-catalyzed nitrilehydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzedreaction, using curved arrows to represent electron flow in each step.

How would you prepare the following carbonyl compounds from a nitrile?

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

How might you carry out the following transformation? More than one step is needed.
See all solutions

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