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Chapter 27: Q 52. (page 1103)

Question: Draw the products of each reaction.

Short Answer

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Answer

Step by step solution

01

Pericyclic reactions  

These reactions are stereospecific. In these reactions, the -bond is formed by the combination of atomic orbitals when they are in the same phase.

02

Oxy-cope rearrangement

In the presence of heat, this reaction forms an enolate that can tautomerize to form a carbonyl group.

03

Products of the given reaction

a. The product of the given reaction is shown here under

b. The product of the given reaction is shown here under.

Product of b.

c. The product of the given reaction is shown here under.

Product of c.

d. The product of the given reaction is shown here under.

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Most popular questions from this chapter

Question: A solution of 5-methylcyclopenta-1,3-diene rearranges at room temperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products are formed from the starting material by a sigmatropic rearrangement involving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene is not formed directly from 5-methylcyclopenta-1,3-diene by a [1,3] rearrangement.

Question: Draw the product formed when each triene undergoes electrocyclic reaction under [1] thermal conditions, [2] photochemical conditions

Question: One step in the synthesis of periplanone B, the chapter-opening molecule, involved anionic oxy-Cope rearrangement of the following unsaturated alcohol. Draw the product that results after protonation of the intermediate enolate.

Question:(a) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene?

(b) Does this reaction proceed in a suprafacial or antarafacial manner under

thermal conditions?

(c) Does this reaction proceed in a suprafacial or antarafacial manner under

photochemical conditions?

Question: Vitamin D3, the most abundant of the D vitamins, is synthesized from 7-dehydrocholesterol, a compound found in milk and fatty fish, such as salmon and mackerel. When the skin is exposed to sunlight, a photochemical electrocyclic ring-opening forms provitamin D3, which is then converted to vitamin D3 by a sigmatropic rearrangement (Section 27.5). Draw the structure of provitamin D3.
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