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Choose the best synthetic route to (CH_(3))_(3)COCH_(3) amongst the following: (a) React (CH_(3))_(3)COH with KOH, then add CH_(3)I . (b) React (CH_(3))_(3)COH with NaOH, then add CH_(3)I. (c) React CH_(3)OH with KOH, then add (CH_(3))_(3)CI. |
| Answer» Solution :The best synthetic route to `(CH_(3))_(3)COCH_(3)` is route (a). In route (b), there is difference in the basicity of hydroxide and t-butoxide, and the CONJUGATE base of `(CH_(3))_(3)COH` is not sufficiently LARGE to affect complete deprotonation of the alcohol. When `CH_(3)I` is added to the reaction mixture, there will be two alkoxides (hydroxide and t-butoxide) competing for the reaction. In route (c), reaction of `CH_(3)O`-- (a strong base) with a tertiary alkyl HALIDE will give `E_(2)`, not `S_(N)2`, products. | |