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Chapter 27: Q 23. (page 1096)

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

Short Answer

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Answer

Step by step solution

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: The bicyclic alkene P can be prepared by thermal electrocyclic ring closure from cyclodecadiene Q or by photochemical electrocyclic ring closure from cyclodecadiene R.Draw the structures of Q and R, and indicate the stereochemistry of the process by which each reaction occurs.

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: Use curved arrows and draw the product of each electrocyclic reaction.

Question:What type of sigmatropic rearrangement is illustrated in each equation?

Question: Draw a stepwise, detailed mechanism for the following reaction.
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