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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

Rank the following compounds in order of increasing acidity. Don鈥檛 look at a table of pKa data to help with your answer.

(a) Benzoic acid, p-methylbenzoic acid, p-chlorobenzoic acid

(b) p-Nitrobenzoic acid, acetic acid, benzoic acid

Draw structures corresponding to the following IUPAC names:

  1. cis-1,2-Cyclohexanedicarboxylic acid

  2. Hepatanedioic acid

  3. 2-Hexen-4-ynoic acid

  4. 4-Ethyl-2-propyloctanoic acid

  5. 3-chlorophthalic acid

  6. Triphenylacetic acid


  7. 2-Cyclobutenecarbonitrile

  8. m-Benzoyl benzonitrile

3-Methyl-2-hexenoic acid (mixture of E and Z isomers) has been identified as the substance responsible for the odour of human sweat. Synthesize the compound from starting materials having five or fewer carbons

How would you carry out the following transformations? More than one step is needed in each case.

Predict the product (s) and provide the mechanism for each reaction below.
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