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Compounds Containing Nitrogen question

2021 · 27 Aug · Shift 1 · Q6
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  5. /2021 · 27 Aug · Shift 1 · Q6

Compounds Containing Nitrogen question

2021 · 27 Aug · Shift 1 · Q6

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Which of the following is not a correct statement for primary aliphatic amines?
  1. A
    The intermolecular association in primary amines is less than the intermolecular association in secondary amines.
  2. B
    Primary amines on treating with nitrous acid solution from corresponding alcohols except mythyl amine.
  3. C
    Primary amines are less basic than the secondary amines.
  4. D
    Primary amines can be prepared by the Gabriel phthalimide synthesis.
View written solutionFree

Correct answer: A

  1. Check option A: Compare intermolecular association in primary vs secondary amines.

Primary amines have the group RNH2RNH_2RNH2​ and secondary amines have R2NHR_2NHR2​NH.

  • In primary amines, there are two N–H bonds, so hydrogen bonding is more extensive.
  • In secondary amines, there is only one N–H bond, so hydrogen bonding is less extensive.

Therefore, intermolecular association is greater in primary amines than in secondary amines.

So the statement “The intermolecular association in primary amines is less than that in secondary amines”\text{“The intermolecular association in primary amines is less than that in secondary amines”}“The intermolecular association in primary amines is less than that in secondary amines” is incorrect.

  1. Check option B: Reaction with nitrous acid.

Primary aliphatic amines react with nitrous acid to form unstable diazonium salts, which decompose to give alcohols: RNH2+HNO2→ROH+N2+H2ORNH_2 + HNO_2 \rightarrow ROH + N_2 + H_2ORNH2​+HNO2​→ROH+N2​+H2​O

Example: C2H5NH2→C2H5OHC_2H_5NH_2 \rightarrow C_2H_5OHC2​H5​NH2​→C2​H5​OH

For methyl amine: CH3NH2+HNO2→CH3OH+N2+H2OCH_3NH_2 + HNO_2 \rightarrow CH_3OH + N_2 + H_2OCH3​NH2​+HNO2​→CH3​OH+N2​+H2​O

So methyl amine also gives the corresponding alcohol, methanol. Hence the phrase "except methyl amine" makes the statement incorrect.

So option B is also incorrect as written.

  1. Check option C: Basic strength.

For aliphatic amines in aqueous solution, the general order is: 2∘>1∘>3∘>NH32^\circ > 1^\circ > 3^\circ > NH_32∘>1∘>3∘>NH3​

Thus primary amines are less basic than secondary amines. So C is correct.

  1. Check option D: Gabriel phthalimide synthesis.

Gabriel synthesis is used to prepare primary aliphatic amines: Phthalimide→alkyl halideN-alkyl phthalimide→hydrolysisRNH2\text{Phthalimide} \xrightarrow[\text{alkyl halide}]{} \text{N-alkyl phthalimide} \xrightarrow[\text{hydrolysis}]{} RNH_2Phthalimidealkyl halide​N-alkyl phthalimidehydrolysis​RNH2​

So D is correct.

  1. Conclusion
  • A is incorrect.
  • B is also incorrect because methylamine does form methanol with nitrous acid.
  • C and D are correct.

Since this is marked as an MCQ (single correct), the intended textbook answer is likely A, based on the standard comparison of hydrogen bonding in primary and secondary amines. However, strictly speaking, B is also not correct as written.

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