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Chapter 27: Q 61. (page 1104)

Question:Draw a stepwise mechanism for the Carroll rearrangement, a reaction that prepares a纬,未-unsaturated carbonyl compound from a尾-keto ester and allylic alcohol in the presence ofbase.

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01

Carroll rearrangement

The Carroll rearrangement involves the conversion of 尾-keto allyl ester into 伪-allyl-尾 -carboxylic acid. It is accompanied by decarboxylation, which gives the final product, i.e., a 纬,未-unsaturated carbonyl system.

02

Mechanism for Carroll rearrangement

The starting materials are given below:

In the presence of a base, the hydroxyl group gets deprotonated. The oxide anion then attacks at the electrophilic carbonyl carbon center, one that is a part of the ester group.

Deprotonation of hydroxyl group and formation of new ester

The ester that is formed tautomerizes and then participates in a [3,3]-sigmatropic rearrangement. The mechanism is shown below:

Tautomerization and Carroll rearrangement

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Most popular questions from this chapter

Question: Using the Woodward鈥揌offmann rules in Table 27.4, predict the stereochemistry of each reaction.

a. a [6 + 4] thermal cycloaddition

b. photochemical electrocyclic ring closure of deca-1,3,5,7,9-pentaene

c. a [4 + 4] photochemical cycloaddition

d. a thermal [5,5] sigmatropic rearrangement

Question:What product would be formed by the disrotatory cyclization of the given triene? Would this reaction occur under photochemical or thermal conditions?

Question: Consider the following electrocyclic ring closure. Does the product form by a conrotatory or disrotatory process? Would this reaction occur under photochemical or thermal conditions?

Question: What product is formed from the Cope or oxy-Cope rearrangement of each starting material?

Question:Using the Woodward鈥揌offmann rules, predict the stereochemical pathway for each cycloaddition:

(a) a [6 + 4] photochemical reaction;

(b) an [8 + 2] thermal reaction.
See all solutions

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