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Chapter 9: Q50P (page 436)

Why is a cumulated diene not formed in the reaction shown below?

Short Answer

Expert verified

Cumulative diene is not formed due to the instability in its transition state.

Step by step solution

01

Reason for not forming cumulative diene

The above reaction proceeds through E2 elimination reaction which has an alkyl like transition state.

Alkyl like transition state get stabilized through the no of alpha Hydrogens attached to the unsaturated bond. For the 1st one, the compound has 6 饾湺 hydrogens around the triple bond whereas for the 2nd compound, there is no such 饾湺 Hydrogens generated around the newly formed double bond. Thus, cumulative diene is not formed.

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Most popular questions from this chapter

Draw the substitution and elimination products for the following reactions, showing the configuration of each product:

a. trans-1-chloro-2-methylcyclohexane + CH3O-

b. cis-1-chloro-2-methylcyclohexane + CH3O鈭�

c. 1-chloro-1-methylcyclohexane + CH3O-

d. 1-chloro-1-methylcyclohexane + CH3OH

If 2-fluoropentane were to undergo an E1 reaction, would you expect the major product to be the more stable alkene or the less stable alkene? Explain your answer.

Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

a. (R)-2-bromohexane + high concentration of CH3O-

b. (R)-3-bromo-3-methylhexane + CH3OH

c. trans-1-chloro-2-methylcyclohexane + high concentration of CH3O-

d. trans-1-chloro-3-methylcyclohexane + high concentration of CH3O-

e. 3-bromo-3-methylpentane + high concentration of CH3CH2O-

f. 3-bromo-3-methylpentane + CH3CH2OH

For each of the following reactions, (1) decide whether an E2 or an E1 occurs, and (2) draw the major elimination product:
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