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Amines

Question
CBSEENCH12011052

In the reaction,

straight H minus straight C identical to CH space rightwards arrow from left parenthesis ii right parenthesis space CH subscript 3 CH subscript 2 Br to left parenthesis straight i right parenthesis space NaNH subscript 2 divided by liq. NH subscript 3 of space straight X
space space space space space space space space space space space space space space space space space space straight X space rightwards arrow from left parenthesis ii right parenthesis space CH subscript 3 CH subscript 2 Br to left parenthesis straight i right parenthesis NaNH subscript 2 divided by liq. NH subscript 3 of space straight Y
X and Y are

  • X=2-butyne; Y= 3-hexyne

  • X=2-butyne;Y=2-hexyne

  • X=1-butyne ;Y = 2-hexyne

  • X=1-butyne; Y =3-hexyne

Solution

D.

X=1-butyne; Y =3-hexyne

NaNH2/liq.NH3 behaves as a base, so it abstracts a proton from acetylene to form acetylide anion followed by alkylation to give compound (X) i.e 1-butyne (X) further reacts with NaNH2/Liq NH3 followed by alkylation with ethyl bromide yields 3-hexyne (Y).
straight H minus straight C identical to straight C minus straight H left parenthesis 1 right parenthesis space rightwards arrow with NaNH subscript 2 divided by liq. space NH subscript 3 on top space straight H minus straight C identical to straight C to the power of minus

straight H minus straight C identical to straight C to the power of minus rightwards arrow with stack CH subscript 3 minus CH subscript 2 minus Br with alkylation below on top space stack straight H minus straight C identical to straight C minus CH subscript 2 CH subscript 3 with bold X with bold 1 bold minus bold butyne below space below

stack straight H minus straight C identical to straight C minus CH subscript 2 CH subscript 3 with bold X with bold 1 bold minus bold butyne below space below space rightwards arrow with left parenthesis straight i right parenthesis space NaNH subscript 2 divided by liq. NH subscript 3 on top space CH subscript 3 CH subscript 2 minus straight C identical to straight C to the power of minus
stack CH subscript 3 CH subscript 2 minus straight C identical to straight C to the power of minus rightwards arrow with CH subscript 3 CH subscript 2 minus Br on top space straight H subscript 3 CCH subscript 2 minus straight C identical to straight C minus CH subscript 2 CH subscript 3 space with stack bold left parenthesis bold Y bold right parenthesis with bold 3 bold minus bold hexyne below below plus HBr