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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]

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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: 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: 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: Use curved arrows and draw the product of each electrocyclic reaction.

Question: (a) Using Figure 27.2 as a guide, draw the molecular orbitals for hexa-2,4-diene. (b) Label the HOMO and the LUMO in the ground state. (c) Label the HOMO and the LUMO in the excited state.

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.
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