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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

Three isomeric pentanols with unbranched carbon chains exist. Which of these isomers, upon dehydration at 180°C, yields only 1-pentene as a product?

Interpretation Introduction

Interpretation:

The isomer of pentanols with unbranched carbon chain that yield 1-pentene as product upon dehydration has to be identified.

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

The isomer of pentanols is said to be unbranched in the problem statement.  Considering this, three isomers are possible and they can be drawn as,

Dehydration at high temperature gives alkene as the product.

When 2-pentanol undergoes dehydration, the products formed are 1-pentene and 2-pentene.  The complete reaction can be given as shown below,

When 3-pentanol undergoes dehydration, the product formed is 2-pentene...

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