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Chapter 20: Q11P (page 653)

How might you prepare 2-phenylethanol from benzyl bromide? More than one step is needed.

Short Answer

Expert verified

The final product, 2-phenylethanol is prepared from benzyl bromide by following method.

Step by step solution

01

Conversion of benzyl bromide into 2-phenylacetic acid.

In the first step,benzyl bromide reacts with NaCNwhich acts as a nucleophile to produce benzylnitrile via a second order nucleophilic substitution mechanism.

In the second step, the hydrolysis of the newly produced benzylnitrilein the presence of aqueous acid H3O+to form 2-phenylacetic acid as shown below.

02

Conversion of 2-phenylacetic acid into 2-phenylethanol

In the third step, 2-phenylacetic acid is converted to 2-phneylethnaol by using the strong reducing agent, LiAIH4. This above reaction is represented as follows:

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Most popular questions from this chapter

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.

Draw and name the following

  1. The eight carboxylic acids with the formula C6H12O2
  2. Three nitriles with the formula C5H7N

Isocitric acid, an intermediate in the citric acid cycle of food metabolism, has the systematic name (2R,3S)-3-carboxy-2-hydroxypentane-dioic acid. Draw the structure.

How would you carry out the following transformations?

Draw structures corresponding to the following IUPAC names:

(a) 2,3-Dimethylhexanoic acid

(b) 4-Methylpentanoic acid

(c)trans-1,2-Cyclobutanedicarboxylic acid

(d)o-Hydroxybenzoic acid

(e) (9Z,12Z)-9,12-Octadecadienoic acid

(f) 2-Pentenenitrile
See all solutions

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