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Q.Among the following isomeric amines select the one which shows the highest boiling point : (CH3)3N ; CH3CH2CH2NH2 ; CH3-CH2-NH-CH3. Name a reagent which can be used to distinguish between the following pair of compounds : (CH3)2NH and (CH3)3N.

Goa GbshseGBSHSE Class 12 Board Exam 2024Subjective· 2mImportance★★★★★
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Among isomeric amines, the primary amine has the highest boiling point because it has two N–H bonds available for intermolecular hydrogen bonding; Hinsberg's test distinguishes secondary from tertiary amines.

Boiling point of amines depends on the extent of intermolecular hydrogen bonding, which in turn depends on the number of N–H bonds:

  • CH3CH2CH2NH2CH_3CH_2CH_2NH_2 (propan-1-amine, a 1° amine) has 2 N–H bonds, so its molecules can hydrogen-bond extensively with each other (like a network), giving it the strongest association and hence the highest boiling point among the three isomers.
  • CH3−CH2−NH−CH3CH_3-CH_2-NH-CH_3 (N-methylethanamine, a 2° amine) has only 1 N–H bond, so it can still hydrogen-bond but less extensively — intermediate boiling point.
  • (CH3)3N(CH_3)_3N (trimethylamine, a 3° amine) has no N–H bond at all, so its molecules cannot hydrogen-bond with each other (only weaker dipole–dipole forces act), giving it the lowest boiling point.

So the primary amine, CH3CH2CH2NH2CH_3CH_2CH_2NH_2, shows the highest boiling point of the three.

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