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Which of the following compounds are chiral and resolvable ? $(i) \;[C_6 H_5 N^+(CH_2CH_2CH_3)(C_2H_5)(CH_3)]Br^ - ; \; (ii) C_6H_5N(CH_3)(C_2H_5) ; \\ (iii)\; CH_3CH_2CH (CH_3) (C_2H_5);\; (iv)\; HO_2C- CO_2H$

$ (a)\;(i)\; and\;(iii) \\ (b) \; (ii)\;and \;(iii) \\ (c) \;(i)\;and \;(iv) \\ (d)\;(ii)\;and (iv) $

1 Answer

(i) is chiral and resolvable since it has a non- super imposable mirror image.
(ii) is chiral but not resolvable because of rapid amine or N - inversion $(2.3 \times 10^{10}\sec)$
(iii) being a tertiary amine it should not be chiral but due top the presence of a chiral carbon, it is chiral as well as resolvable.
(iv) $CO_2H$ groups do not provide sufficient steric hindrance to prevent rotation about carbon- carbon single bond and hence diphenic acid is easily racemised and hence cannot be resolved.
So (i) and (iii) resolvable.
Hence a is the correct answer.
answered Feb 28, 2014 by meena.p

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