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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

Step by step solution

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: 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: (a) How many 蟺 molecular orbitals are present in deca-1,3,5,7,9-pentaene (CH2=CH-CH=CH-CH=CH-CH=CH-CH=CH2)? (b) How many are bonding MOs and how many are antibonding MOs ? (c) How many nodes are present in 蠄1*? (d) How many nodes are present in 蠄10*?

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

Question: What type of pericyclic reaction is illustrated in each reaction?

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