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Chapter 27: Q 12. (page 1088)

Question:Consider cycloheptatrienone and ethylene, and draw a possible product formed from each type of cycloaddition:

(a) [2 + 2]

(b) [4 + 2]

(c) [6 + 2]

Short Answer

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Answer

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01

Cycloaddition reaction

Cycloaddition reaction is a C-C bond-forming addition reaction between two compounds having pi-bonds. It is similar to an electrocyclic reaction and can occur under thermal or photochemical conditions.

A cycloaddition reaction can be [2+2], [4+2], or [6+2], depending on the types of bonds present in the reacting systems.

02

[2+2] Cycloaddition reaction

Cycloheptatrienone can undergo [2+2] addition with ethylene.The reaction is shown below:

03

[4+2] Cycloaddition reaction

The two pi-bonds of cycloheptatrienone can undergo [4+2] addition with ethylene.The reaction is shown below:

04

[6+2] Cycloaddition reaction

All the pi-bonds of cycloheptatrienone can undergo [6+2] addition with ethylene.The reaction is shown below:

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Most popular questions from this chapter

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 the products of each reaction.

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: Show how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.

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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