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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

What lactol (cyclic hemiacetal) is formed from intramolecular cyclization of each hydroxy aldehyde?

a.

b.

Draw the products (including stereoisomers) formed when benzaldehyde (C6H5CHO) is treated with each Wittig reagent

a.

b.

Safrole is a naturally occurring acetal isolated from sassafras plants. Once used as a common food additive in root beer and other beverages, it is now banned because it is carcinogenic. What compounds are formed when safrole is hydrolysed with aqueous acid?

Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomersformed in this reaction from both A and B. Explain why this process gives an opticallyinactive product mixture from A, and an optically active product mixture from B.

Which carbonyl group in each pair absorbs at a higher frequency?

a.

b.
See all solutions

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