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← IIT-JEE 2009 · Paper 1
ChemistryMatrix match+8Question 20 of 60

IIT-JEE 2009 · Paper 1, Chemistry question 20

Match each of the compounds in Column I with its characteristic reaction(s) in Column II.

Column I

  • A
    CHX3CHX2CHX2CN\ce{CH3CH2CH2CN}
  • B
    CHX3CHX2OCOCHX3\ce{CH3CH2OCOCH3}
  • C
    CHX3−CH=CH−CHX2OH\ce{CH3-CH=CH-CH2OH}
  • D
    CHX3CHX2CHX2CHX2NHX2\ce{CH3CH2CH2CH2NH2}

Column II

  • P
    Reduction with Pd−C/HX2\ce{Pd-C/H2}
  • Q
    Reduction with SnClX2/HCl\ce{SnCl2/HCl}
  • R
    Development of foul smell on treatment with chloroform and alcoholic KOH
  • S
    Reduction with diisobutylaluminium hydride (DIBAL-H)
  • T
    Alkaline hydrolysis
Mark every match for each entry
PQRST
A
B
C
D
Answer and worked solution

Official answer: A → P, Q, S, T; B → S, T; C → P; D → R

  • A, butanenitrile: HX2\ce{H2}/Pd-C reduces it to the amine; SnClX2/HCl\ce{SnCl2/HCl} (Stephen reduction) and DIBAL-H give the aldehyde; alkaline hydrolysis gives the carboxylate. → P, Q, S, T.
  • B, ethyl acetate: DIBAL-H reduces the ester (to the aldehyde at low temperature); alkaline hydrolysis (saponification). → S, T.
  • C, but-2-en-1-ol: the C=C is hydrogenated by HX2\ce{H2}/Pd-C. → P.
  • D, butan-1-amine: a primary amine gives the foul-smelling isocyanide with CHClX3\ce{CHCl3}/alc. KOH (carbylamine test). → R.

Answer: A → P, Q, S, T; B → S, T; C → P; D → R

Topics:Cyanides and isocyanidesAcid derivativesAminesAlcohols
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