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Question

Consider the following transformations.
HCCCH2CH2CH3H3CCH=CHCH2CH3
Which reaction sequence will bring about the above transformation?

A
(i)H2/PdC (ii)Cl2/hv (iii)KOH/EtOH
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B
(i)H2/Pd CaCO3 (ii)HBr (iii)KOH/EtOH
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C
(i)NaNH2/H2 (ii)Br2/CCl4 (iii)KOH/EtOH
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D
(i)Pd/CaCO3 (ii)Cl2CCl4 (iii)KOH/EtOH
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Solution

The correct option is B (i)H2/Pd CaCO3 (ii)HBr (iii)KOH/EtOH
First reaction is Partial hydrogenation of alkyne in presence of Lindlar's catalyst then electrophilic addition of HBr and then dehydrohalogenation. HCCCH2CH2CH3H2,Pd−−−CaCO3
H2C=CHCH2CH2CH3HBr
H3CBr|CHCH2CH2CH3alc.KOHH3CCH=CHCH2CH3

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