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Which one of the following two methods is appropriate for the preparation of neopentyl chloride (Me_(3)C CH_(2)Cl) and why? (1) (CH_3)_(3)C CH_(2)Ohoverset(HCl)rarr (CH_3)_(3)C CH_(2)Cl+H_(2)O (ii) (CH_3)_(4)Coverset(Cl_(2)//hv)(rarr)(CH_3)_(3)C CH_(2)Cl+HCl |
Answer» Solution :All the H-atoms of neopentane `(Me_(4)C)` are equivalent and the intermediate radical does not undergo rearrangement. So, the second method leads to the formation of neopentyl chloride as the only product. This method is, therefore, appropriate for the preparation of neopentyl chloride.  On the other hand in the first reaction, the interediate `1^(@)` carbocation is highly unstabel and READILY rearranges to a more STABLE `3^(@)` carbocation. So, 2-chloro-2-methylbutane is OBTAINED ALMOST exclusively instead of neopentyl chloride. Therefore, the first method is not appropriate for the preparation of neopentyl chloride. .
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