Simmons- Smith reaction of cyclohexene with diiodomethane gives a single product, but the analogous reaction of cyclohexene with 1,1-diiodoethane gives in low yield a mixture of two isomeric methylcyclopropane products. The two products are to be identified the difference between them is to be stated. Concept introduction: In Simmons-Smith reaction an alkene is treated with CH 2 I 2 in the presence of Zn/Cu couple. When CH 2 I 2 reacts with Zn/Cu, iodomethylzinc iodide, ICH 2 ZnI, is formed which then transfers a CH 2 group to the double bond in alkene to form a cyclopropane ring in the product. When diiodides with more carbons are used then depending upon the arrangement of the groups on the cyclopropane ring different isomeric products are possible. To identify: The two isomeric products formed when cyclohexene reacts with 1,1-diiodoethane are to be identified and the difference between them is to be stated.

Question

Acrolein and 1,3-cyclohexadiene react in a one-step concerted manner to yield a single product. Give the structure of the product. What kind of reaction is this an example of? In terms of this reaction, how would you classify acrolein? How would you classify 1,3-cyclohexadiene? Hint: acrolein is not a systematic name so you may need to look up its structure if you are not already familiar with it.

Answer 1

Question

Chapter 8.SE, Problem 63AP

Interpretation Introduction

Interpretation:

Simmons- Smith reaction of cyclohexene with diiodomethane gives a single product, but the analogous reaction of cyclohexene with 1,1-diiodoethane gives in low yield a mixture of two isomeric methylcyclopropane products. The two products are to be identified the difference between them is to be stated.

Concept introduction:

In Simmons-Smith reaction an alkene is treated with CH₂I₂ in the presence of Zn/Cu couple. When CH₂I₂ reacts with Zn/Cu, iodomethylzinc iodide, ICH₂ZnI, is formed which then transfers a CH₂ group to the double bond in alkene to form a cyclopropane ring in the product. When diiodides with more carbons are used then depending upon the arrangement of the groups on the cyclopropane ring different isomeric products are possible.

To identify:

The two isomeric products formed when cyclohexene reacts with 1,1-diiodoethane are to be identified and the difference between them is to be stated.

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