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Chapter 9: Q116P (page 391)

Two elimination products are obtained from the following E2 reaction

a. What are the elimination products?

b. Which is formed in greater yield? (Hint:See Problem 91.)

Short Answer

Expert verified

a. The elimination products are,

b. The 1st product forms with grater yield.

Step by step solution

01

Definition of E2 reaction

E2 reaction is an elimination reaction where H abstraction and C-Br bond breaking happens simultaneously having a trans periplanar arrangement between the C-H and C-Br bond.

02

Reaction mechanism of the given reactions

a. The elimination products are given below,

b. Energy taken in breaking the C-D bond is higher than breaking of C-H bond. Thus, formation of product following KH path has greater yield.

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Most popular questions from this chapter

a. Indicate how each of the following factors affects an E1 reaction:

1. The strength of the base

2. The concentration of the base

3. The solvent

b. Indicate how each of the same factors affects an E2 reaction.

cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.

Draw the structure of DDE.

a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol.

b. Are all the products optically active?

c. How would the products differ if the starting material were the trans isomer? Are these products optically active?

d. Will the cis enantiomers or the trans enantiomers form substitution products more rapidly?

e. Will the cis enantiomers or the trans enantiomers form elimination products more rapidly?

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

a. ethoxide ion or tert-butoxide ion

b. -OCN or -SCN

c. Cl- or Br-

d. CH3S- or CH3O-
See all solutions

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