Why is the carbocation form of 3-bromo-3-methylhexane (when its LG leaves) achiral?
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- Anonymous1 decade agoFavorite Answer
3-Bromo-3-methylhexane is chiral because the carbon bearing bromo group, methyl group, ethyl group and propyl group (four different substitutent) is tetrahedral (sp3 hybridisation). ( In a tetrahedral carbon if the four substituent are different then there is no axis or plane of symmetry present, that makes the compound Chiral)
But when a carbocation forms by leaving bromo substitent from 3-bromo-3-methylhexane, it becomes planar in shape (sp2 hybridisation for carbocation). And for planar molecules there is a plane of symmetry present which makes this species Achiral.
I hope it makes you understood this.