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Topic: Major Product formed in LiAlH4 Reaction  (Read 2512 times)

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Offline T33

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Major Product formed in LiAlH4 Reaction
« on: August 30, 2018, 11:44:02 AM »
I understand that Lithium aluminum hydride is a powerful reducing agent. So the carboxyl group would be reduced to OH, but answer B is incorrect. Would the H3O+ cause the Ester to reduce to OH? Answer choice E?

Offline wildfyr

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Re: Major Product formed in LiAlH4 Reaction
« Reply #1 on: August 30, 2018, 12:59:55 PM »
Why don't you look in your textbook how LAH reacts with esters? Or a quick google. I think the answer will pop out once you do.

Offline Babcock_Hall

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Re: Major Product formed in LiAlH4 Reaction
« Reply #2 on: August 30, 2018, 01:33:24 PM »
As a general practice when dealing in redox chemistry, I sometimes find it helpful to assign oxidation numbers to carbon atoms.

Offline 93R

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Re: Major Product formed in LiAlH4 Reaction
« Reply #3 on: September 04, 2018, 06:02:54 PM »
Once 1st reduction is done to get ketone to 2ndary alcohol, the ester C=O is reduced to an OH.

This is B, but this is a lactol, in equilibrium with the open chain aldehyde, which can further be reduced to tetra-ol (if that's even the correct term haha). I'd guess E too.

Offline Babcock_Hall

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Re: Major Product formed in LiAlH4 Reaction
« Reply #4 on: September 05, 2018, 08:28:34 AM »
93R,

As a general practice, we try to lead the OP to the right answer, but for a dormant thread, it probably does not matter.

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