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Topic: Chemoselectivity in reduction  (Read 5043 times)

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Offline cupsoftea

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Chemoselectivity in reduction
« on: December 11, 2014, 02:54:16 PM »
I did an experiment, reducing the following selectivity to target either functional group

{MOD Edit: snip out monster link to Google image search}

1) using Sn/HCl to reduce the NO2 group to NH2
2) using NaBH4 to reduce the carbonyl to an alcohol

In both cases the choice of reducing agent is selective

My understanding is that the NaBH4 is too mild to reduce the NO2 group

But I am not sure why the Sn/HCL doesn't reduce carbonyls?

Any suggestions much appreciated
« Last Edit: December 19, 2014, 09:55:20 AM by Arkcon »

Offline kriggy

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Re: Chemoselectivity in reduction
« Reply #1 on: December 19, 2014, 01:57:01 PM »
I think that Sn/HCl can reduce carbonyl group, it depends on conditions

Offline Altered State

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Re: Chemoselectivity in reduction
« Reply #2 on: December 19, 2014, 06:13:21 PM »
Following "Modern Projects and Experiments" (http://www.amazon.com/Modern-Projects-Experiments-Organic-Chemistry/dp/0716739216), you can indeed selectively reduce the nitro group of that compound using 1) Sn/HCl 2) NaOH/H2O



Source:
http://www.foothill.edu/psme/armstrong/selectivereduction.shtml



Further reading: https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/chapt15.htm


Note that even a benzaldehyde group is not reduced by Sn/HCl

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