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Topic: Product formed after reduction of 3-ethoxy-4-hydroxybenzaldehyde?  (Read 7504 times)

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Offline Kobsessed

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Ok I don't know if there's an error in my paper or not.  We will be doing a lab this week where the objective is to "use sodium borohydride to reduce 3-ethoxy-4-benzaldehyde".

The first q asks me to draw the structure of 3-ethoxy-4-hydroxybenzaldehyde. Is this different from the above or did they forget to add a "hydroxy"? But anyways I know the structure.

The second questions asks to draw the structure of the product obtained after the reduction of 3-ethoxy-4-hydrobenzaldehyde. We have no background information and just the objectve and proceadures for the lab so I had to check online. I think the product is Methyl Diantilis? The structure is the same except the C double bond O is replaced with another ether group. Am I correct?

The third question asks to identify the elctrophile and nucleophile in the reduction reaction. I have no idea how to do that.
« Last Edit: May 28, 2009, 12:31:34 AM by Kobsessed »

Offline gfunk

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Re: Product formed after reduction of 3-ethoxy-4-hydroxybenzaldehyde?
« Reply #1 on: May 28, 2009, 01:55:43 AM »
1) The molecule "3-ethoxy-4-benzaldehyde" doesn't really make sense.  The aldehydic functionality is assumed to be in the "1" position, and with the "3" position occupied with the ethoxy group, the "4" doesn't describe anything.  So I'd say it's the 4-hydroxy.

2) So, you're reducing something in this experiment.  Think about what functionalities you have in your molecule.  Will you reduce the hydroxyl?  Ethoxy group?  Aromatic ring?  Aldehyde?  What can be feasibly reduced?  Check out http://en.wikipedia.org/wiki/Sodium_borohydride#Organic_synthetic_applications and that'll show you sodium borohydride's application.

3) What is sodium borohydride?  The most important part, the borohydride is a source of hydride ions (H-).  Are nucleophiles electron-rich or electron poor?  Go from there.

Good luck! :)
Grad Student - Organic Chemistry
University of Alberta

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