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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

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

How could you convert each of the following compounds into butanoic acid? Write each step showing the reagents needed.

(a) 1-Butanol

(b) 1-Bromobutane

(c) 1-Butene

(d) 1-Bromopropane

(e) 4-Octene

How would you prepare the following carboxylic acids?

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

(b) CH3CH2CH2CO2HfromCH3CH2CH2Br

The two 1H NMR spectrashown here belong to crotonic acid (trans-CH3CH=CHCO2H) and methacrylic acid (CH2=C(CH3)CO2H). Which spectrum corresponds to which acid? Explain.

The 1H and 13C NMR spectra below belong to a compouns with formula C6H10O2. Propose a structure for this compound.
See all solutions

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