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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

Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound

a. Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrins that results

b. Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms

The Kafor dichloroacetic acid is3.32脳10-2. Approximately what percentage of the acid is dissociated in a 0.10 M aqueous solution?

Assume you have a mixture of naphthalene and benzoic acid that you want to separate. How might you take advantage of the acidity of one component in the mixture to effect a separation?

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

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 CO鈧侶 group?
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