Conceptual Organic!

Chemistry Level 3

What is the product when Toluene is treated with concentrated Nitric Acid?

Para Nitro Toluene None of these Trinitro Toluene Meta nitro Benzoic Acid Ortho nitro toluene No reaction Benzoic Acid

Prakhar Bindal by Prakhar Bindal , 22, India

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1 solution

Prakhar Bindal
Dec 11, 2016

Firstly No Electrophilic Substitution will take place as there is no H2SO4 For generation of electrophile .

But Nitric Acid is a very strong oxidising agent and hence can oxidise toluene to Benzoic Acid

4 Helpful 0 Interesting 0 Brilliant 0 Confused

Exactly! :p

Sumanth R Hegde - 4 years, 6 months ago

but due to very high oxidizing nature of conc nitric acid, toluene would be oxidized to CO2 + H2O , this same problem occurs in preparation of picric acid. also I want to add that benzene is not that much oxidizable so not much problem occurs in nitration of benzene. so answer should be none. please correct me if wrong

AYUSH JAIN - 4 years, 6 months ago

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see this

http://chemistry.stackexchange.com/questions/18467/oxidation-of-toluene-to-benzoic-acid-in-presence-of-kmno4

Prakhar Bindal - 4 years, 6 months ago

If potassium permangante cant oxidise benzoic acid further i dont think HNO3 Can

Prakhar Bindal - 4 years, 6 months ago

In My opinion unless mentioned we do not oxidise benzene. but still i will write under normal conditions. coz you know Benzene and ketones are not easily oxidisable. you need to warm them up to a sufficiently high temperature.

Prakhar Bindal - 4 years, 6 months ago

yes i agree. HNO3 with aniline in 75% conc results in charring. Our teacher had told charring of toluene but I am unable to find strong evidence of this fact. also i agree with your logic of kmn04. thanks for replying and keep posting.

AYUSH JAIN - 4 years, 6 months ago

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My pleasure keep solving!

Prakhar Bindal - 4 years, 6 months ago

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