benzyl or tertiary???

Till today i thought that benzyl cation was more stable than tertiary...
But today I saw in a Engineering book that actually they both have almost equal stability but given a chioce tertiary is favoured...

can anybody confirm it.....

6 Answers

1
Vicky Chijwani ·

i think tertiary is more stable as it has a whopping 9 hyperconjugants and 3 +I groups... while benzyl has 0 hyperconjugants + resonance (as far as i know phenyl group withdraws by negligible -I effect also)...

11
Mani Pal Singh ·

order of stability of carbocations r

3°>2°>1°

1
greatvishal swami ·

tertiary is more stable

1
Akand ·

ya its all about HYPERCONJUGATION over here.................nothing else i think

1
kamalendu ghosh ·

Yeah tertiary's more stable.... but in RK GUPTA it is givenbenzyl is more stable

1
greatvishal swami ·

reason tert has 9 hyperconjugation and +I

benzyl has resonace 5 and -I

-I plays villain

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