Q.

In the compound below, which nitrogen is protonated first when treated with HCl?

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a

1 is protonated because it is sp2 hybridised

b

2 is protonated because it is sp3 hybridized

c

1 is protonated because its lone pair is not involved in aromaticity

d

2 is protonated because its lone pair is not involved in aromaticity

answer is C.

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Detailed Solution

Lone pair of electron on nitrogen labelled 2 is part of aromatic delocalization, not available for donation to H+ while lone pair on nitrogen labelled 1 is not the part of aromatic system, protonated more easily as:
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