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Chapter 28: Q42P (page 1239)

Propose a mechanism for the following reaction:

Short Answer

Expert verified

A Claisen rearrangement is a [3,3] sigmatropic rearrangement of an allyl vinyl ether.

It takes place under thermal conditions, it contains the rearrangement of six electrons and makes a six-membered transition state

Step by step solution

01

Step 1:Claisen rearrangement 

A Claisen rearrangement is a [3,3] sigmatropic rearrangement of an allyl vinyl ether.

It takes place under thermal conditions, it contains the rearrangement of six electrons and makes a six-membered transition state

02

Step 2:Cope rearrangement

A Cope rearrangement is a [3,3] sigmatropic rearrangement of a 1,5-diene.

After tautomerization, we will get the final product.

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Most popular questions from this chapter

Explain why compound A will not undergo a ring-opening reaction under thermal conditions, but compound B will.

Two products are formed in the following [1,7] sigmatropic rearrangement, one due to hydrogen migration and the other to deuterium migration. Show the configuration of the products by replacing A and B with the appropriate atoms (H or D).

Problem:a. For conjugated systems with two, three, four, five, six, and seven conjugatedπ bonds, construct quick MOs (just draw the lobes at the ends of the conjugated system as they are drawn on pages 1220 and 1221) to show whether the HOMO is symmetric or antisymmetric.

b. Using these drawings, convince yourself that the Woodward–Hoffmann rules in Table 28.1 are valid.

cis-3,4-Dimethylcyclobutene undergoes thermal ring opening to form the two products shown. One of the products is formed in 99% yield, the other in 1% yield. Which is which?

Show how norbornane can be prepared from cyclopentadiene.
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