Q47E.

Question

Question: The cis and trans isomers of 2-butene give different cyclopropane products in the Simmons–Smith reaction. Show the structures of both, and

explain the difference.

Step-by-Step Solution

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Answer

Answer

Structures of the reaction products are:

1Step 1: Simmons- Smith reaction

Simmons- Smith’s reaction was given by Howard Ensign Simmons, Jr. and Ronald D. Smith. Reagent Diiodomethane in the presence of zinc-copper complex will form methylene free radical, and it will react with double bonds of alkene and form a cyclopropane ring.

2Step 2: Explanation

In Simmons- smith reaction, alkene will act as a nucleophile and form a cyclopropane ring, and a cyclopropane ring will form on the less hindered side of the compound.

3Step 3: Geometry of product

The cis isomer of 2- butene will form cis product, and trans-2- butane will form trans-1,2-dimethylcyclopropane. Therefore, we can say that the Simmons- smith reaction will do syn- addition. Hence, the product of reactions are:

Q46E

Q48E

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