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Chapter 9: Q86P (page 452)

Which species in each pair is more stable?

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掳 carbocation>2掳 carbocation>1掳 carbocation

5. As the carboanion intermediate is formed so the stability order 1掳 carboanion>2掳 carboanion>3掳 carboanion


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掳 carbocation>2掳 carbocation>1掳 carbocation

5. As the carboanion intermediate is formed so the stability order 1掳 carboanion>2掳 carboanion>3掳 carboanion

02

Final answer

Less substituted carboanion is more stable.

More substituted carbocation is more stable.

Stabilized by electron delocalization.

More substituted carbocation is more stable.

Stabilized by electron delocalization.

Less substituted carboanion is more stable.

More substituted carbocation is more stable.

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Most popular questions from this chapter

Four alkenes are formed from the E1 reaction of 3-bromo-2,3-dimethylpentane and methoxide ion. Draw the structures of the alkenes and rank them according to the amount that would be formed.

Question:Draw the elimination products for each of the following E2 reactions; if the products can exist as stereoisomers, indicate which stereoisomers are obtained.

a. (2S,3S)-2-chloro-3-methylpentane + high concentration of CH3O-

b.(2S,3R)-2-chloro-3-methylpentane + high concentration of CH3O-

c.(2R,3S)-2-chloro-3-methylpentane + high concentration of CH3O-

d.(2R,3R)-2-chloro-3-methylpentane + high concentration of CH3O-

e.3-chloro-3-ethyl-2,2-dimethylpentane + high concentration of CH3CH2O-

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

a. ( R )-2-bromopentane + CH3O-

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

c. benzyl chloride + CH3CH2OH

d. allyl chloride + CH3OH

e. 1-bromo-2-butene + CH3O-

f. 1-bromo-2-butene + CH3OH

Amines are good nucleophiles, even though they are neutral. How would the rate of an SN2 reaction between an amine and an alkyl halide be affected if the polarity of the solvent is increased?

What products are formed when the following stereoisomer of 2-chloro-1,3-dimethylcyclohexane reacts with methoxide ion?
See all solutions

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