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Chapter 27: Q 60. (page 1104)

Question: a) What is the structure of C, which is formed by oxy-Cope rearrangement of B with NaOEt?

(b) Draw a stepwise mechanism for the conversion of C to the bicyclic alcohol D.

Short Answer

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Answer

Step by step solution

01

Oxy-cope rearrangement

The oxy-cope rearrangement involves the rearrangement of the unsaturated alcoholic structure of the compound to form an enal or enone by undergoing tautomerization.

02

Attack of nucleophile

The nucleophile attacks the most acidic hydrogen, i.e., -hydrogen, to the carbonyl group and abstracts it, thus creating a carbocationic center.

03

Products of the given reaction

(a). The structure of C consists of an “enal” center. The structure of C is given hereunder

(b). The mechanism of conversion of C into D is given hereunder

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Most popular questions from this chapter

Question: What product is formed when each compound undergoes thermal electrocyclic ring opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.

Question: What type of cycloaddition occurs in Reaction [1]? Draw the product of a similar process in Reaction [2]. Would you predict that these reactions occur under thermal or photochemical 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:Using the Woodward–Hoffmann rules, predict the stereochemical pathway for each cycloaddition:

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

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

Question: What product is formed by the [3,3] sigmatropic rearrangement of each compound?
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