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Reduction, Oxidation and Hydrolysis in Organic Chemistry
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Dissolving metal reductions (Birch, Na/NH3)
JEE Advanced level
Single correct option
Difficulty 3 of 3
ro036
Hex-3-yne is reduced with Na in liquid
NH
X
3
and the product is treated with
Br
X
2
in
CCl
X
4
(anti addition). The final product is
A
racemic (3R,4R)- and (3S,4S)-3,4-dibromohexane
B
meso-3,4-dibromohexane
C
3,3,4,4-tetrabromohexane
D
(Z)-3,4-dibromohex-3-ene
Answer: B
Na/
NH
X
3
gives (E)-hex-3-ene. Anti addition of
Br
X
2
to an E-alkene gives the meso dibromide.
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