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Chapter 27: Q 45. (page 1102)

Question: Draw the product of the [3,3] sigmatropic rearrangement of each compound.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

[3,3] sigmatropic rearrangement

The rearrangement of a 1,5 diene to its 1,5-diene isomer by the cleavage of an existing sigma bond and the formation of a new sigma bond is termed as the [3,3] sigmatropic rearrangement

02

[3,3] sigmatropic rearrangements of the given compounds

The [3,3] sigmatropic rearrangement of compound a is shown below.

[3,3] sigmatropic rearrangement of compound a

The [3,3] sigmatropic rearrangement of compound b is shown below.

[3,3] sigmatropic rearrangement of compound b

The [3,3] sigmatropic rearrangement of compound c is shown below.

[3,3] sigmatropic rearrangement of compound c

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Most popular questions from this chapter

Question: What type of cycloaddition occurs in Reaction [1]? Draw the product of a similar process in Reaction [2]. Would you predict that these reactions occur under thermal or photochemical conditions?

Question: Draw the product of each electrocyclic reaction.

a. the thermal electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-triene

b. the photochemical electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-triene

c. the thermal electrocyclic ring-opening of cis-5-ethyl-6-methylcyclohexa-1,3-diene

d. the photochemical electrocyclic ring-opening of trans-5-ethyl-6-methylcyclohexa-1,3- diene

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

Question: Using the Woodward鈥揌offmann 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

Question: What product is formed from the Cope or oxy-Cope rearrangement of each starting material?
See all solutions

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