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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

What spectroscopic method could you use to distinguish among the following three isomeric acids? Tell what characteristic features you would expect for each acid

a) CH3(CH2)3CO2H - Pentanoic acid

b) (CH3)2CHCH2CO2H- 3-Methylbutanoic acid

c) (CH3)3CCO2H -2,2-Dimethylpropanoic acid

Give IUPAC names for the following compounds:

In humans, the final product of purine degradation from DNA is uric acid, pKa = 5.61, which is excreted in the urine. What is the percent dissociation of uric acid in urine at a typical pH = 6.0? Why do you think uric acid is acidic even though it does not have a CO₂H group?

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

Naturally occurring compounds called terpenoids, which we’ll discuss in section27-5, are biosynthesized by a pathway that involves loss of carbon dioxide from 3-phosphomevalonate 5-diphosphate to yield isopentenyl diphosphate. Use curved arrows to show the mechanism of this reaction.
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