The structure of the two isomeric tertiary alcohols formed by the addition of phenylmagnesium bromide to 4 − t e r t − b u t y l c y c l o h e x a n o n e are to be drawn. Concept introduction: Grignard reagnts react with ketones , producing tertiary alcohols. In a chair conformation of substituted cyclohexane, the largest group should be oriented in the equatorial position in the most stable conformation. Acid catalyzed dehydration of alcohols produces alkenes. The hydroxyl group attached to the alpha carbon atom is protonated by the acid. The hydrogen atom from the beta carbon atom and the protonated hydroxyl group are eliminated and new carbon-carbon double bond is formed.

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Chapter 15, Problem 23P

Interpretation Introduction

Interpretation:

The structure of the two isomeric tertiary alcohols formed by the addition of phenylmagnesium bromide to 4−tert−butylcyclohexanone are to be drawn.

Concept introduction:

Grignard reagnts react with ketones, producing tertiary alcohols.

In a chair conformation of substituted cyclohexane, the largest group should be oriented in the equatorial position in the most stable conformation.

Acid catalyzed dehydration of alcohols produces alkenes. The hydroxyl group attached to the alpha carbon atom is protonated by the acid. The hydrogen atom from the beta carbon atom and the protonated hydroxyl group are eliminated and new carbon-carbon double bond is formed.

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