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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: researcher on November 20, 2009, 10:14:40 AM

Title: reduction of nitrobenzene
Post by: researcher on November 20, 2009, 10:14:40 AM

Can you reduce nitrobenzene to aniline using LiAlH₄ ?

I learned this reaction only happened with Sn or Zn, but most of the reductions use LiAlH₄ or NaBH₄.

Title: Re: reduction of nitrobenzene
Post by: stewie griffin on November 20, 2009, 10:22:10 AM

Yes. Nitro groups are kind of weird. There's various metals that will reduce an NO2 to an NH2 group including the one's you mention and also iron and i think a few others. LiAlH4 will also do the same. Just keep in mind that on a test you may have other functional groups that LiAlH4 would reduce as well even though you want to keep them intact. In that case it's helpful to know these other metals to go from nitro to amine.

Title: Re: reduction of nitrobenzene
Post by: Med90 on November 21, 2009, 10:14:57 AM

Reduction of nitro group to NH2 using LAH is little messy.
how about using catalytic hydrogenation as in following reference
http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0030

Title: Re: reduction of nitrobenzene
Post by: jdmfob on November 22, 2009, 10:29:55 PM

Reduction of nitrobenzene to aniline using LiAlH4 is possible.  However, it is not normally used due to formation of other intermediates. 

Source: http://www.scribd.com/doc/22672674/8303119-039-Reacts-Benzene