Arrange the following in order of decreasing reactivity in the S_N2 reaction: l-

Question

Arrange the following in order of decreasing reactivity in the S_N2 reaction: l-bromo-3-methylbutane, 2-bromo-2-methylbutane, 1-bromopentane, l-bromo-2-methylbutane Arrange the following in order of decreasing reactivity in the S_N1 reaction: 2-bromopropane, bromomethane, 1-bromopropane, 2-bromo-2-methylpropane Arrange the following in order of decreasing reactivity in the S_N1 reaction: 2-chloropentane, 2-bromopentane, 1-chloropentane, 3-bromo-3-methylpentane No reaction of either type with vinylic (=CH-X) or aryl halides:

Explanation / Answer

For SN2 reactions, the nucleophile has to attack from the back of leaving group. Thus the more bulkier the alkyl group, less is the reactivity. (primary > secondary > tertiary)

1)SN2 order

1-bromopentane > 1-bromo-3-methylbutane > 1-bromo-2methylbutane > 2-bromo-2-methylbutane

Fro Sn1 reactions the carbocation is the intermediate. Thus the more stable carbocation formation increses the rate of reaction. [tertiary > secondary>primary > methyl]

2) SN1 order

2-bromo2-methylpropane > 2-bromopropane > 1-bromopropane > bromomethane

Among the leaving groups the order of reactivity is I > Br > Cl > F

3) SNN1 order

3- bromo-3-methylpentane > 2-bromopentane > 2-chloropentane > 1-chloropentane

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