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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: aRomatik Benzenoid on January 11, 2012, 01:18:33 PM

Title: CARBOCATIONS
Post by: aRomatik Benzenoid on January 11, 2012, 01:18:33 PM

is 3 degree carbocation always more stable than 2 degree and is 2 degree always more stable than 1 degree??

Title: Re: CARBOCATIONS
Post by: discodermolide on January 11, 2012, 03:04:27 PM

Quote from: aRomatik Benzenoid on January 11, 2012, 01:18:33 PM

is 3 degree carbocation always more stable than 2 degree and is 2 degree always more stable than 1 degree??

In general, yes, that is so.

Title: Re: CARBOCATIONS
Post by: Mitch on January 11, 2012, 03:28:36 PM

Not if the tertiary carbocations were themselves attached to carbocations. Mwhahahahaha....

Otherwise, discodermolide is correct.

Title: Re: CARBOCATIONS
Post by: aRomatik Benzenoid on January 12, 2012, 01:36:55 PM

i was thinking dat tertiary carbocation means that C+ attached to 3 carbon atoms and its stability is explained by hyperconjugation but if C+ is attached to 3 neo butyl groups dere is no alpha hydrogen therefore it is not stable!!!! den  C+-Ch3 is more stable than it

Title: Re: CARBOCATIONS
Post by: Mitch on January 12, 2012, 04:08:54 PM

Quote from: aRomatik Benzenoid on January 12, 2012, 01:36:55 PM

i was thinking dat tertiary carbocation means that C+ attached to 3 carbon atoms and its stability is explained by hyperconjugation but if C+ is attached to 3 neo butyl groups dere is no alpha hydrogen therefore it is not stable!!!! den  C+-Ch3 is more stable than it

I'm sure it also has to do with inductive effects. Hyperconjugation is the rationalization of last resort.

Title: Re: CARBOCATIONS
Post by: Telamond on January 13, 2012, 03:11:12 AM

Why can't the C-C sigma-bond donate into the empty p-orbital?