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

Predict the major organic product(s) of the following reactions. Indicate which of the following mechanisms is in operation: SN1, SN2, E1, or E2.

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Predict the major organic product(s) of the following reactions. Indicate which of the following mechanisms is in operation: SN1, SN2, E1, or E2.

(c) (4pts) Mechanism: heat (E1) CH3OH + 1.5pts each _E1 _ (1pt) Br CH3OH (d) (4pts) Mechanism: SN1 (1pt) (e) (3pts) 1111 I H 10 Ill!! H LDA THF (solvent) Mechanism: E2 (1pt) NC (f) Bri!!!!! CH3 NaCN (3pts) acetone Mechanism: SN2 (1pt) (SN1) -OCH3 OCH3 1.5pts each 2pts for either product 1pt if incorrect stereochemistry H Br (g) “,、 (3pts) H CH3OH +21 Mechanism: SN2 (1pt) H CH3 2pts 1pt if incorrect stereochemistry H 2pts 1pt if incorrect stereochemistry

A mixture of butyl acrylate and 4'-chloropropiophenone has been taken for proton NMR analysis. Based on this proton NMR, determine the relative percentage of each compound in the mixture