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Chapter 27: Q 47. (page 1102)

Question: What product is formed from the [5,5] sigmatropic rearrangement of the following unsaturated ether?

Short Answer

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Answer

Step by step solution

01

Step 1: [5,5]  sigmatropic shift

The 5,5sigmatropic shift is associated with the intramolecular rearrangement of the group at the fifth position and the fifth position of the other group.

The new sigma bond is formed between the fifth positions of the groups.

02

Explanation

In the given conversion, the group at the fifth position rearranges itself. Therefore, it is a 5,5 sigmatropic shift.

5,5sigmatropic shift.

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Most popular questions from this chapter

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.

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 type of sigmatropic rearrangement is illustrated in each equation?

Question: a) What product is formed when triene N undergoes thermal electrocyclic ring closure? (b) What product is formed when triene N undergoes photochemical ring closure? (c) Label each process as conrotatory or disrotatory.

Question: Using the Woodward–Hoffmann rules in Table 27.4, predict the stereochemistry of each reaction.

a. a [6 + 4] thermal cycloaddition

b. photochemical electrocyclic ring closure of deca-1,3,5,7,9-pentaene

c. a [4 + 4] photochemical cycloaddition

d. a thermal [5,5] sigmatropic rearrangement
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