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Chapter 26: Q 27. (page 1070)

Draw the products (including stereoisomers) formed in each reaction.

Short Answer

Expert verified

Answer

Product of a

Product of b

d.Product of d

Step by step solution

01

Simmons-Smith reaction

The reaction involves the carbenoid formation that undergoes a cheletropic reaction, followed by the reaction with the C=C (alkene) to form a cyclopropane. This reaction is stereoselective.

02

Addition of dihalocarbenes to alkenes

The reaction takes place with syn-addition. The position of the substituted groups on alkene remains the same in cyclopropane.

03

Products of the given reaction

a. The stereoselective product is shown hereunder.

Product of a

b. The following reaction is the addition of dihalocarbenes to alkenes. The syn-addition product is shown hereunder.


c. The following reaction is the addition of dihalocarbenes to alkenes. The syn-addition product is shown hereunder.

Product of c

d. The following reaction is the addition of dihalocarbenes to alkenes. The syn-addition product is shown hereunder.

Product of d

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Most popular questions from this chapter

When certain cycloalkenes are used in metathesis reactions, ring-opening metathesis polymerization (ROMP) occurs to form a high molecular weight polymer, as shown with cyclopentene as the starting material. The reaction is driven to completion by relief of strain in the cycloalkene.

What products are formed by ring-opening metathesis polymerization of each alkene?

What reagents are needed to carry out transformations [1]–[3] in the synthesis of aldehyde A? A can be converted to the antitumor agent maytansine in several steps.

What product is formed by ring-closing metathesis of each compound?

a.

b.

Devise a synthesis of diene A from (Z)-2-bromostyrene as the only organic starting material. Use a Suzuki reaction in one step of the synthesis.

Many variations of ring-closing metathesis have now been reported. Tandem ring-opening– ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon– carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.

a.

b.
See all solutions

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