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Chapter 30: Q.30-9 (page 1030)

When a 2,6-disubstituted allyl phenyl ether is heated in an attempted Claisen rearrangement, migration occurs to give the p-allyl product as the result oftwo sequential pericyclic reactions. Explain.

Short Answer

Expert verified

The product is formed by Claisen rearrangement which is followed by Cope rearrangement. This involves [3,3] sigmatropic reaction, it also follows enolization

Step by step solution

01

It involoves two pericyclic reactions.

The overall reaction given below follows 2 pericyclic reactions

02

The overall mechanism involve[3,3] sigmatropic reaction.

The product is formed by Claisen rearrangement which is followed byCope rearrangement. This involves [3,3] sigmatropic reaction, it also follows enolization. (As shown in the figure below).

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Most popular questions from this chapter

What stereochemistry—antarafacial or suprafacial—would you expect to observe in the following reactions?

(a) A photochemical [1,5] sigmatropic rearrangement

(b) A thermal [4 + 6] cycloaddition

(c) A thermal [1,7] sigmatropic rearrangement

(d) A photochemical [2 + 6] cycloaddition

1,3-Cyclopentadiene reacts with cycloheptatrienone to give the productshown. Tell what kind of reaction is involved, and explain the observed result.Is the reaction suprafacial or antarafacial?

What stereochemistry would you expect for the product of the Diels–Alder reaction between (2E,4E)-2,4-hexadiene and ethylene? What stereochemistry would you expect if (2E,4Z)-2,4-hexadiene were used instead?

(2E,4Z,6Z,8E)-2,4,6,8-Decatetraene has been cyclized to give 7,8-dimethyl-1,3,5-cyclooctatriene. Predict the manner of ring-closure- conrotatory or disrotatory for both thermal and photochemical reactions, and predict the stereochemistry of the product in each case.

trans-3,4-Dimethylcyclobutene can open by two conrotatory paths to give either (2E,4E)-2,4-hexadiene or (2Z,4Z)-2,4-hexadiene. Explain why both products are symmetry-allowed, and then account for the fact that only the 2E,4Eisomer is obtained in practice.
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