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Chapter 27: Q 23. (page 1096)

Question: What compound forms geranial (Figure 21.6) by a Cope rearrangement ?

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01

Geranial

Geranial comes under the category of compounds termed terpenoids. It is an isomer of citral comprising the molecular formula and is termed as citral-A.

02

Cope rearrangement

There are several [3,3] sigmatropic rearrangements, and one among them is the Cope rearrangement. A molecule of 1,5-diene gets subjected to cope rearrangement to give rise to isomeric 1,5-diene.

03

Identifying the compound that forms geranial by Cope rearrangement

Geranial undergoes [3,3] sigmatropic rearrangement to form 3, 3-dimethyl-2-(prop-1-en-2-yl)pent-4-enal. The chemical reaction can be given as:

Compound that forms geranial by Cope rearrangement

Hence, the compound formed by the Cope rearrangement of geranial is 3, 3-dimethyl-2-(prop-1-en-2-yl)pent-4-enal.

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Most popular questions from this chapter

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: Classify each reaction as an electrocyclic reaction, a cycloaddition, or a sigmatropic rearrangement. Label the 蟽 bonds that are broken or formed in each reaction.

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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.

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