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Chapter 10: PROBLEM 10.57 (page 423)

Question: Draw a stepwise mechanism for the following reaction, which results in ring expansion of a six-membered ring to a seven-membered ring.

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01

Generation of carbocation  

The carbocations generated by the addition of acids to alkenes may undergo shifting (1,2-hydrogen or 1,2-methyl), depending upon their stability.

The stability order of the carbocations is3掳>2掳>1掳 .

02

1,2-hydrogen and methyl shift

The stability of carbocations enables 1,2-hydrogen and methyl shift. After the shifting of methyl and hydrogen to adjacent positions, which is the most stable carbocation.

03

Explanation

The reaction of the given compound with water and sulfuric acid proceeds via 1,2-bond shift to generate a carbocation. The carbocation gives a tertiary alcohol product.

The mechanism is shown below:

Reaction mechanism

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Most popular questions from this chapter

Question: Draw a stepwise mechanism that shows how all three alcohols are formed from the bicyclic alkene.

Question: What three alkenes (excluding stereoisomers) can be used to prepare 3-chloro-3-methylhexane by addition of HCl?

Question: Using cis- and trans-hex-3-ene, demonstrate that the addition of HCl is not a stereospecific reaction. Draw the structure of the stereoisomers formed from each alkene.

Question: How many rings and 蟺 bonds does a compound with molecular formula C10H14 possess? List all possibilities.

Question: How many degrees of unsaturation are present in each compound?

  1. C6H6
  2. role="math" localid="1648637368534" C8H18
  3. C7H8O
  4. C7H11Br
  5. C5H9N
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