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Chapter 10: PROBLEM 10.55 (page 422)

Question: Using cis- and trans-hex-3-ene, demonstrate that the addition of HCl is not a stereospecific reaction. Draw the structure of the stereoisomers formed from each alkene.

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01

Stereospecific reaction  

A stereospecific reaction gives either R or S isomer in a greater yield. The racemic mixture does not contain a stereospecific product as it has R and S isomers in equal amounts.

02

Addition of HCl to an alkene

The alkene forms an intermediate when it reacts with HCl. It is due to the protonation of the double bond. Protonation gives a positive charge on the carbon present on the other side of the double bond.

This positive charge is highly stable, and therefore, chloride ion attacks it.

03

Explanation

Cis and trans-hex-3-ene react with HCl to give the same racemic mixture. Therefore, the products are not stereospecific.

Reaction of cis-hex-3-ene and trans-hex-3-ene with HCl

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