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Chapter 21: 62P (page 817)

Design a stepwise synthesis to convert cyclopentanone and 4-bromobutanal to hydroxy aldehyde A.

Short Answer

Expert verified

Carbonyl compounds are protected by forming either open or closed acetals by reacting with suitable alcohol.

4-bromobutanal reacts with ethylene glycol to form a ring acetal. This would protect the carbonyl group increasing the chemoselectivity of the halide ion.

Protection of carbonyl compound

Step by step solution

01

Acetal formation

Carbonyl compounds are protected by forming either open or closed acetals by reacting with suitable alcohol.

4-bromobutanal reacts with ethylene glycol to form a ring acetal. This would protect the carbonyl group increasing the chemoselectivity of the halide ion.

Protection of carbonyl compound

02

Organometallic compound

The compound would react with magnesium to form the corresponding Grignard reagent (RMgX).

Formation of Grignard reagent

03

Nucleophilic reaction

The Grignard reagent would attack the carbonyl carbon and is hydrolyzed to form the corresponding alcohol.

Nucleophilic addition

04

Deprotection

The compound is protonated in order to deprotect the carbonyl group giving the required product A.

Deprotection to form A

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Most popular questions from this chapter

A solution of acetone (CH3)2C=O in ethanol CH3CH2OH in the presence of a trace of acid was allowed to stand for several days, and a new compound of molecular formula C7H16O2 was formed. The IR spectrum showed only one major peak in the functional group region around 3000 cm-1 , and the 1H-NMR spectrum is given here. What is the structure of the product?

Draw the products of each reaction.

a.

b.

Show two different methods to carry out the following transformation: a one-step method using a Wittig reagent, and a two-step method using a Grignard reagent. Which route, if any, is preferred?

Give the IUPAC name for each compound.

a.

b.

c.

d.

e.

f.

Draw a stepwise mechanism for the following reaction
See all solutions

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