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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?

a. How many stereogenic centers are present in -D-galactose?

b. Label the hemiacetal carbon in -D-galactose.

c. Draw the structure of -D-galactose.

d. Draw the structure of the polyhydroxy aldehyde that cyclizes to - and

-D-galactose.

e. From what you learned in Section 21.16B, what product (s) is (are) formed

when -D-galactose is treated with CH3OH and an acid catalyst?

Etoposide, sold as a phosphate derivative with the trade name of Etopophos, is used for the treatment of lung cancer, testicular cancer, and lymphomas. (a) Locate the acetals in etoposide. (b) What products are formed when all of the acetals are hydrolyzed with aqueous acid?

An unknown compound D exhibits a strong absorption in its IR spectrum at 1692 cm-1 . The mass spectrum of D shows a molecular ion at m/z = 150 and a base peak at 121. The 1H- NMR spectrum of D is shown below. What is the structure of D?

Draw the products of each reaction.

a.

b.
See all solutions

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