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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: (a) How many π molecular orbitals are present in deca-1,3,5,7,9-pentaene (CH2=CH-CH=CH-CH=CH-CH=CH-CH=CH2)? (b) How many are bonding MOs and how many are antibonding MOs ? (c) How many nodes are present in ψ1*? (d) How many nodes are present in ψ10*?

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: What product is formed by [3,3] sigmatropic rearrangement of the following compound? Clearly indicate the stereochemistry around all tetrahedral stereogenic centers.

Question: Draw structures for A, B, and C in the following reaction sequence and identify the process that converts B to C.

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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