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Chapter 27: Q 14. (page 1090)

Question:Draw the product (including stereochemistry) formed from each pair ofreactants in a thermal [4 + 2] cycloaddition reaction.

Short Answer

Expert verified

For a [4+2] cycloaddition, the bond formation can occur superficially under thermal conditions.

The [4+2] cycloaddition considering HOMO of diene and LUMO of alkene is shown below:

Bond formation between HOMO of diene and LUMO of alkene

Step by step solution

01

[4+2] Cycloaddition reactions

For a [4+2] cycloaddition, the bond formation can occur superficially under thermal conditions.

The [4+2] cycloaddition considering HOMO of diene and LUMO of alkene is shown below:

Bond formation between HOMO of diene and LUMO of alkene

02

Determination of products

a. Both the reactants are redrawn, and the [4+2] cycloaddition is carried out. The product is shown below:

b. Both the reactants are redrawn, and the [4+2] cycloaddition is carried out. The product is shown below:

[4+2] cycloaddition of compound b

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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: The endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rain forests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resulting conjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.

Question:Draw a stepwise mechanism for the Carroll rearrangement, a reaction that prepares aγ,δ-unsaturated carbonyl compound from aβ-keto ester and allylic alcohol in the presence ofbase.

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

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?
See all solutions

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