Consider the following transformations. H−C≡C−CH2−CH2−CH3→H3C−CH=CH−CH2−CH3 Which reaction sequence will bring about the above transformation?
A
(i)H2/Pd−C(ii)Cl2/hv(iii)KOH/EtOH
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B
(i)H2/PdCaCO3(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)Cl2−CCl4(iii)KOH/EtOH
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Solution
The correct option is B(i)H2/PdCaCO3(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. H−C≡C−CH2−CH2−CH3H2,Pd−−−−→CaCO3 H2C=CH−CH2−CH2−CH3HBr⟶ H3C−Br|CH−CH2−CH2−CH3alc.KOH⟶H3C−CH=CH−CH2−CH3