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Compounds Containing Nitrogen question

2014 · Shift 0 · Q13
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Compounds Containing Nitrogen question

2014 · Shift 0 · Q13

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
On heating an aliphatic primary amine with chloroform and ethanolic potassium hydroxide, the organic compound formed is:
  1. A
    an alkyl cyanide
  2. B
    an alkyl isocyanide
  3. C
    an alkanol
  4. D
    an alkanediol
View written solutionFree

Correct answer: B

  1. Identify the reaction

Heating an aliphatic primary amine with chloroform (CHCl3)(\mathrm{CHCl_3})(CHCl3​) and ethanolic KOH is the carbylamine reaction.

The general reaction is:

RNH2+CHCl3+3KOH→RNC+3KCl+3H2O\mathrm{RNH_2 + CHCl_3 + 3KOH \rightarrow RNC + 3KCl + 3H_2O}RNH2​+CHCl3​+3KOH→RNC+3KCl+3H2​O

where RNH2\mathrm{RNH_2}RNH2​ is a primary amine and RNC\mathrm{RNC}RNC is an isocyanide (also called carbylamine).

  1. What product is formed?

The product RNC\mathrm{RNC}RNC is an alkyl isocyanide when the amine is aliphatic.

So, an aliphatic primary amine gives:

RNH2→alc. KOHCHCl3, heatRNC\mathrm{RNH_2 \xrightarrow[alc.\ KOH]{CHCl_3,\ heat} RNC}RNH2​CHCl3​, heatalc. KOH​RNC
  1. Check the options
  • A: an alkyl cyanide   (RCN)\; (\mathrm{RCN})(RCN) → Incorrect
  • B: an alkyl isocyanide   (RNC)\; (\mathrm{RNC})(RNC) → Correct
  • C: an alkanol → Incorrect
  • D: an alkanediol → Incorrect
  1. Final answer

The organic compound formed is an alkyl isocyanide.

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