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Chapter 9: Q57. (page 378)

Question: Draw a stepwise, detailed mechanism for the following reaction.

Short Answer

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Answer

The mechanism of the reaction is as shown below.

Step by step solution

01

Step-by-Step SolutionStep 1: Stability of carbocation

During the (unimolecular) reaction, the most stable carbocation intermediate will be formed if the rearrangement of alkyl shift or hydride shift does not lead to the formation of the most stable carbocation

02

The mechanism of the given reaction

This reaction takes place in the presence of a sulfuric acid catalyst.

The secondary carbocation becomes the most stable 3°carbocationdue to the alkyl shift. Then, will be eliminated, and it leads to the formation of the respective alkene

Mechanism of the reaction

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Most popular questions from this chapter

Question: What alkyl halides are formed when each ether is treated with HBr?

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Question: Although alcohol V gives a single alkene W when treated with POCl3 and pyridine, three isomeric alkenes (X–Z) are formed on dehydration with H2SO4. Draw a stepwise mechanism for each reaction and explain why the difference occurs.

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Question: When each halohydrin is treated with NaH a product of molecular formulaC4H8Ois formed. Draw the structure of the product and indicate its stereochemistry.

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Question: If the reaction of an alcohol with PBr3follows anSN2 mechanism, what is the stereochemistry of the alkyl bromide formed from (R)-butan-2-ol?
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