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Haloalkanes and Haloarenes
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Reactions of alkyl halides with nucleophiles
JEE Main level
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Difficulty 2 of 3
hx060
Arrange the following in decreasing order of rate of SN1 solvolysis in aqueous ethanol.
A
(
CH
X
3
)
X
3
CBr
>
CH
X
3
Br
>
CH
X
3
CH
X
2
Br
>
(
CH
X
3
)
X
2
CHBr
B
(
CH
X
3
)
X
2
CHBr
>
(
CH
X
3
)
X
3
CBr
>
CH
X
3
CH
X
2
Br
>
CH
X
3
Br
C
(
CH
X
3
)
X
3
CBr
>
(
CH
X
3
)
X
2
CHBr
>
CH
X
3
CH
X
2
Br
>
CH
X
3
Br
D
CH
X
3
Br
>
CH
X
3
CH
X
2
Br
>
(
CH
X
3
)
X
2
CHBr
>
(
CH
X
3
)
X
3
CBr
Answer: C
SN1 rate follows carbocation stability:
3
∘
>
2
∘
>
1
∘
>
methyl
. Hyperconjugation and the +I effect of alkyl groups stabilise the cation. The order is tert-butyl > isopropyl > ethyl > methyl bromide.
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