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Haloalkanes and Haloarenes
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Stereochemical outcomes of substitution
JEE Advanced level
Single correct option
Difficulty 3 of 3
hx214
(R)-Butan-2-ol is treated with
SOCl
X
2
and pyridine to give X. X is then treated with excess hydroxide under conditions of pure SN2 to give Y. Y is
A
(R)-butan-2-ol
B
(S)-butan-2-ol
C
butan-1-ol
D
racemic butan-2-ol
Answer: A
Step 1 (SOCl2/pyridine) inverts: (R)-alcohol gives (S)-2-chlorobutane. Step 2 (SN2 with OH-) inverts again: (S)-chloride gives (R)-alcohol. Two inversions return the original configuration.
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