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Topic: Stabilities of isoborneol vs borneol [HELP NEEDED]  (Read 12280 times)

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Offline DDuckPuppy

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Stabilities of isoborneol vs borneol [HELP NEEDED]
« on: March 06, 2008, 09:04:03 PM »
Hey everyone,

This question is killing me. In the laboratory camphor was reduced by methanol/sodium borohydride to create isoborneol and borneol. The question is which one is more stable and explain with a mechanism. I want to say that isoborneol is more stable because of the steric hinderance from the OH group, which would prevent further reactions from occuring. But I can't seem to find any information that would cofirm whether I'm right or wrong.

AND I have no idea how to explain with a mechanism. Would I just show how the borohydride could continue to attack the borneol?

Thanks so much for the help.

Offline azmanam

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Re: Stabilities of isoborneol vs borneol [HELP NEEDED]
« Reply #1 on: March 06, 2008, 09:22:13 PM »
do you know what the difference is between the structures of borneol and isoborneol?

Do you know what the mechanism is of the borohydride reduction of camphor?

note: After camphor is attacked by borohydride, no further reaction with borohydride will occur.
Knowing why you got a question wrong is better than knowing that you got a question right.

Offline DDuckPuppy

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Re: Stabilities of isoborneol vs borneol [HELP NEEDED]
« Reply #2 on: March 06, 2008, 09:40:00 PM »
I do know that the hydroxyl group in borneol is in the endo position, while in the isoborneol it is in the exo position. I'm pretty sure that the isoborneol is the more stericlly hindered one.

Would the mechanism be similar to the hydroboration of the C=C bonds?

Offline azmanam

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Re: Stabilities of isoborneol vs borneol [HELP NEEDED]
« Reply #3 on: March 07, 2008, 06:04:46 AM »
Quote
I do know that the hydroxyl group in borneol is in the endo position, while in the isoborneol it is in the exo position. I'm pretty sure that the isoborneol is the more stericlly hindered one.

good so far.  do you know what endo and exo means? and why that makes the exo one more hindered

Quote
Would the mechanism be similar to the hydroboration of the C=C bonds?

no.  much simpler than that.  check your notes or Google it.
Knowing why you got a question wrong is better than knowing that you got a question right.

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