Chapter 8.13, Problem 20P

Interpretation Introduction

Interpretation:

The products formed from acid-catalyzed hydration of racemic (±)-4-methyl-1-pentene are to be given. The relative amounts of products formed and whether the product mixture is optically active or not is to be stated.

Concept introduction:

Hydration of chiral alkenes lead to the formation of a chiral alcohol. The reaction occurs through the formation of a carbocation. If during the reaction the configuration on the chiral carbon in the alkene remains unchanged in the product and a new chiral centre is also created, then two diastreomeric isomers differing in the configuration on the newly created chiral carbon result. The diasteremeric isomers are usually obtained in different ratios (not 50:50) as the approach of the reagent towards the carbocation from either the top or bottom, for steric reasons, is hindered.

To give:

The products formed from acid-catalyzed hydration of racemic (±)-4-methyl-1-pentene.

To state:

The relative amounts of products formed.

To state:

Whether the product mixture is optically active or not.