The basic strength of 1,8-bis(dimethylamino)n | vedclass

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Question

(B) The correct answer is $(b)$.$1,8-$bis(dimethylamino)naphthalene,also known as a 'proton sponge',exhibits exceptionally high basicity.In $1-$dimeth

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steric inhibition of resonance

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(B) The correct answer is $(b)$.$1,8-$bis(dimethylamino)naphthalene,also known as a 'proton sponge',exhibits exceptionally high basicity.In $1-$dimethylaminonaphthalene,the lone pair on the nitrogen atom is involved in resonance with the naphthalene ring,which decreases its availability for protonation.In $1,8-$bis(dimethylamino)naphthalene,the two bulky $-N(CH_3)_2$ groups are forced into close proximity at the $1$ and $8$ positions. This causes steric crowding,which forces the lone pairs out of the plane of the naphthalene ring,thereby inhibiting resonance.Since the lone pairs cannot participate in resonance,they are more available for protonation,making the molecule a much stronger base.

The basic strength of $1,8-$bis(dimethylamino)naphthalene is $10^{10}$ times more than $1-$dimethylaminonaphthalene. The reason for this high basic strength is:

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