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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: science123 on October 15, 2010, 02:33:53 AM

Title: Does clemmensen reduction affect nitro groups on benzene?
Post by: science123 on October 15, 2010, 02:33:53 AM

Can we selectively reduce aldehydes/ketones on a benzene ring which also has a nitro group without converting it to an amino group using Zn (Hg) / HCl ?

Title: Re: Does clemmensen reduction affect nitro groups on benzene?
Post by: SVXX on October 15, 2010, 02:53:30 AM

Yes they do affect nitro groups on the benzene ring, forcing them to undergo a dissolving metal reduction into an amino groups. The mechanism is similar to that of DMR using tin and HCl.

Title: Re: Does clemmensen reduction affect nitro groups on benzene?
Post by: science123 on October 15, 2010, 01:45:57 PM

I was told that Zn/HCl reduces nitro groups very slowly in comparison with Sn/HCl. Thus, Zn/HCl can be used to reduce aldehydes/ketones that are on benzene ring along with nitro groups since nitro reduction is very slow in comparison to carbonyl reduction. I don't know how correct is that.