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Chapter 27: Q 40. (page 1101)

Question: What cycloaddition products are formed in each reaction? Indicate the stereochemistry of each product.

Short Answer

Expert verified

Answer

Cycloaddition products

(a)

(b)

Step by step solution

01

Cycloaddition reaction

In a cycloaddition reaction, two unsaturated molecules undergo an addition reaction to form a cyclic product.

02

Cycloaddition products

  • When substituted ethylene is irradiated with UV-light, an electron is promoted from a (ground state) to(excited state) orbital.

  • Photochemical cycloaddition takes place between the excited HOMO of one molecule and the ground state LUMO of another molecule.
  • The result is a mixture of the ground state and excited state of the ethylene molecule.

HOMO and LUMO interaction

  • If there is stereochemistry in the dienophile, then it is reproduced in the product.

Thus, cis and trans dienophiles give different diastereomers of the product.

a. Cis dienophile

cis substituted cyclobutene

b. Trans dienophile

trans substituted cyclobutene

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Most popular questions from this chapter

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]

Question: a) What is the structure of C, which is formed by oxy-Cope rearrangement of B with NaOEt?

(b) Draw a stepwise mechanism for the conversion of C to the bicyclic alcohol D.

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: 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.

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?
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