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Topic: Glucose derivative and HBr question  (Read 3788 times)

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Offline omegatomato

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Glucose derivative and HBr question
« on: April 03, 2007, 09:52:07 AM »
Hello all

I'm trying to figure out what happens when you have a molecule that is just alpha (D)-glucose (in the chair conformer) except instead of the alcohol groups, they're all OC=OPh (so the carbon is single bonded to a phenyl group, double bonded to an oxygen and single bonded to an oxygen that is then bonded to the rest of the ring).

Then, there are three different reactions I'm trying to figure out.

What happens when HBr is added?
What happens when NaBH4 is added?
What happens when NaCH3OH is add?

Note- I mean those as three seperate reactions.  One where HBr is added to the [original] sugar.  One where NaBH4 is added to the [original] sugar.  One where NaCH3OH is added to the [original] sugar.

I've drawn it all out below.

Thank you very much for your help.
« Last Edit: April 03, 2007, 10:16:59 AM by omegatomato »

Offline omegatomato

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Re: Glucose derivative and HBr question
« Reply #1 on: April 03, 2007, 01:04:15 PM »
Anybody have any idea on this one?

Offline Yggdrasil

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Re: Glucose derivative and HBr question
« Reply #2 on: April 03, 2007, 11:34:28 PM »
Our Forum Rules state that you must show that you've attempted to answer the question before we can help.  However, I will give you some questions to guide you to the answers:

What type of functional groups are present in the molecule?
HBr is an acid.  What will an acid do to the functional group?
NaBH4 is a reducing agent.  It can reduce certain functional groups, but not others.  Will it reduce the functional groups in your molecule?

Also, NaCH3OH makes no sense.  Do you mean sodium methoxide (CH3ONa)?

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