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Chapter 9: Q32P (page 422)

What percentage of the reaction described in Problem 31 takes place by the E2 pathway when [HO-] = 0.0025 M?

Short Answer

Expert verified

1. It is a two step reaction.

2. In this carbocation is formed.

3. In this negative ion will attack from the side where there is less number of bulkier groups.

4. As the carbocation intermediate is formed so the stability order 3° carbocation>2° carbocation>1° carbocation.

Step by step solution

01

How SN1 reaction proceed

1. It is a two step reaction.

2. In this carbocation is formed.

3. In this negative ion will attack from the side where there is less number of bulkier groups.

4. As the carbocation intermediate is formed so the stability order 3° carbocation>2° carbocation>1° carbocation.

02

How SN2 reaction proceed

1. It is one step reaction.

2. In this nucleophile attacks the back side of the carbon.

3. In this one intermediate stage is formed.

4. In intermediate stage one group is leaving group and one group is attacking group.

5. In this inversion of reaction takes place.

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Most popular questions from this chapter

Rank the following alkyl bromides from most reactive to least reactive in an SN2 reaction:

1-bromo-2-methylbutane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, and 1-bromopentane.

a. Explain why the reaction of an alkyl halide with ammonia gives a low yield of primary amine.

b. Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide with an azide ion (-N3), followed by catalytic hydrogenation. (Hint: An alkyl azide is not nucleophilic.)

The pKa of acetic acid in water is 4.76. What effect will a decrease in the polarity of the solvent have on the pKa? Why?

Which isomer reacts more rapidly in an E2 reaction: cis-1-bromo-4-tert-butylcyclohexane or trans-1-bromo-4-tert-butylcyclohexane? Explain your answer.

Propose a mechanism for the following reaction:
See all solutions

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