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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: Classify each pericyclic reaction as an electrocyclic reaction, cycloaddition, or sigmatropic rearrangement. Indicate whether the stereochemistry is conrotatory, disrotatory, suprafacial, or antarafacial.

Question: Heating A results in two successive [3,3] sigmatropic rearrangements鈥擟laisen reaction followed by Cope reaction鈥攖o afford 尾-Sinensal, a component of mandarin orange oil. What is the structure of 尾-sinensal?

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: (a) Using Figure 27.2 as a guide, draw the molecular orbitals for hexa-2,4-diene. (b) Label the HOMO and the LUMO in the ground state. (c) Label the HOMO and the LUMO in the excited state.

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