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Question:

(a) Write the structure of main products when aniline reacts with the following reagents: (i) Br2 water (ii) HCl (iii) (CH3CO)2O/pyridine (b) Arrange the following in the increasing order of their boiling points: C2H5NH2, C2H5OH, (CH3)3N (c) Give a simple chemical test to distinguish between the following pair of compounds: (CH3)2NH and (CH3)3N

Solution:

(b) Increasing order of boiling point (CH3)3N < C2H5NH2 < C2H5OH
Alcohols have higher boiling points compared to that of amines because oxygen, being more electronegative, forms stronger hydrogen bonds compared to that of nitrogen. In tertiary amines, there is no hydrogen to form hydrogen bonds and hence, has the lowest boiling point.