In substitution reactions, (CH3)3C-I reacts at the same rate with Br and CI even though Br is a more reactive nucleophile than Cl-. Why?

EBK A SMALL SCALE APPROACH TO ORGANIC L
4th Edition
ISBN:9781305446021
Author:Lampman
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Chapter20: Nucleophilic Substitution Reactions: Competing Nucleophiles
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In substitution reactions, (CH3)3C-I reacts at
the same rate with Br and Cl even though
Br is a more reactive nucleophile than Cl-.
Why?
Select one:
A. (CH3)3C-Br reacts by SN1 mechanism
whose rate is independent of
nucleophile reactivity.
B. The t-butyl group sterically hinders
nucleophiles, making different
nucleophiles appear to react at the
same rate.
C. (CH3)3C-Br reacts by SN2 mechanism
and therefore all nucleophiles react at
the same rate regardless of their
reactivity.
D. The t-butyl carbocation is so reactive,
the measurable rate of it's reaction
with different nucleophiles is
imperceptible.
Transcribed Image Text:In substitution reactions, (CH3)3C-I reacts at the same rate with Br and Cl even though Br is a more reactive nucleophile than Cl-. Why? Select one: A. (CH3)3C-Br reacts by SN1 mechanism whose rate is independent of nucleophile reactivity. B. The t-butyl group sterically hinders nucleophiles, making different nucleophiles appear to react at the same rate. C. (CH3)3C-Br reacts by SN2 mechanism and therefore all nucleophiles react at the same rate regardless of their reactivity. D. The t-butyl carbocation is so reactive, the measurable rate of it's reaction with different nucleophiles is imperceptible.
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