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

Question: Draw the product formed when diene M undergoes disrotatory cyclization. Indicate the stereochemistry at new hybridized carbons. Will the reaction occur under thermal or photochemical conditions?

Question: Classify each pericyclic reaction as an electrocyclic reaction, cycloaddition, or sigmatropic rearrangement. Indicate whether the stereochemistry is conrotatory, disrotatory, suprafacial, or antarafacial.
See all solutions

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