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Topic: arrange according to stability  (Read 4361 times)

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Offline tortoise

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arrange according to stability
« on: March 07, 2007, 12:06:58 AM »
Please arrage these ions in desceding order of stability:
a) CH3+  b) CH2R+  c) CHR2+  d) CR3+

Offline Yggdrasil

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Re: arrange according to stability
« Reply #1 on: March 07, 2007, 12:49:43 AM »
Please read the Forum Rules[/url] before posting.  We will not help you answer question that you have not shown any attempts to answer on your own.  However, I will offer one bit of help.  A very helpful tutorial on carbocations can be found at the following site:

http://web.chem.ucla.edu/%7Eharding/tutorials/cc.pdf

Offline tortoise

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Re: arrange according to stability
« Reply #2 on: March 07, 2007, 01:04:33 AM »
sorry, but I really don't know the answer... a solution given by my friend is a - d - b - c. I don't know why it is.

oh thank you for your link. it helps a lot. yeah the order is (page 5)

CH3+ (least stable) < RCH2+ < R2CH+ < R3C+ (most stable)

Offline Yggdrasil

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Re: arrange according to stability
« Reply #3 on: March 07, 2007, 01:10:44 AM »
Yup, that is the correct order.  Now, the real question is do you understand why?  (if you don't I can try to explain it)

Offline tortoise

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Re: arrange according to stability
« Reply #4 on: March 07, 2007, 01:13:11 AM »
actually.... I don't know   :(  Help me explain it pls.

Offline Yggdrasil

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Re: arrange according to stability
« Reply #5 on: March 07, 2007, 01:22:46 AM »
In one word the answer is hyperconjugation.  Basically, since carbocations have empty p-orbitals, they gain stability by filling their empty p-orbital with electrons from neighboring sources.  One way that this can happen is through overlap with neighboring sigma bonds.  For example, lets say you have a methyl group bonded to a carbocation.  When the C-H bond of the methyl group is aligned with the empty p-orbital of the carbocation, some of the electron density in the C-H sigma bond can delocalize to help fill and stabilize the empty p-orbital.  This phenomenon is known as hyperconjugation.  Hydrogens which are directly bonded to the carbocation cannot stabilize the empty p-orbital because the hydrogen's electrons lie in the C+-H bond which is orthogonal to the empty p-orbital and therefore cannot donate electron density.

Does this make sense?

Offline tortoise

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Re: arrange according to stability
« Reply #6 on: March 07, 2007, 01:32:01 AM »
sure! it's surely simplier than the lecture you've given. thanks a lot!

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