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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Chapter
Section
BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

Draw the structures of all possible organic products that can form when the alcohol 3-methyl-3-hexanol is dehydrated.

Interpretation Introduction

Interpretation:

The structures of all possible organic products that can form when the alcohol 3-methyl-3-hexanol undergoes dehydration has to be drawn.

Concept Introduction:

Dehydration reaction is the loss of water from a single reactant.  Alcohol undergoes dehydration reaction to form alkene.  Sulfuric acid acts as a catalyst for hydration of alkene at room temperature.  The same sulfuric acid acts as a dehydrating agent when treated with alcohol at high temperature.  If the reaction is carried out at a lower temperature, the loss of water molecule takes place from two molecule of reactant.  This results in the formation of ether.  Primary alcohol when treated with sulfuric acid at lower temperature (140°C) gives ether as the product while secondary and primary alcohol gives alkene as the main product in good yield.

Explanation

Given alcohol is 3-methyl-3-hexanol.  The structure of this alcohol can be drawn as shown below,

The above drawn alcohol is a tertiary alcohol.  Therefore, the dehydration reaction only takes place even at lower temperature.  A hydroxyl group and a hydrogen atom has to be removed for dehydration to take place...

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