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Of the two bromoderivatives C_(6)H_(5)CH(CH_(3))Br and C_(6)H_(5)CH(C_(6)H_(5))Br, which one is more reactive in S_(N)1 substitution reaction and why? |
Answer» SOLUTION :In `S_(N)1` reaction, reactivity depends upon the stability of the intermediate carbocation. Thus,  The carbocation (II) DERIVED from `C_(6)H_(5)CH(C_(6)H_(5))Br` is stabilized by +R-effect of the two `C_(6)H_(5)` groups the carbocation (I) derived from `C_(6)H_(5)CH(CH_(3))Br` is stabilized by +R-effect of one `C_(6)H_(5)` group and +I-effect of the `CH_(3)` group. since +R-effect is much STRONGER than +I-effect, therefore, carbocation (II) is more stable than carbocation (I). thus, `C_(6)H_(5)CH(C_(6)H_(5))Br` is more reactive than `C_(6)H_(5)CH(C_(6)H_(5))Br` is more reactive than `C_(6)H_(5)CH(CH_(3))Br` in `S_(N)1` substitution reaction. |
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