Sciencemadness Discussion Board

Nitromethane, Nitro methanol and Methyl nitrate !!

HGOPOO - 24-8-2011 at 07:48

Hi
I want to know what is the difference between
Nitromethane, Nitromethanol and Methyl nitrate

many names for one thing ? or what ??
I want a detailed explanation please
Thanx

redox - 24-8-2011 at 07:54

The first picture is nitromethane. It is a nitroalkane.

The second picture is nitromethanol. It is a nitroalcohol. I have never heard of nitromethanol before.

The third picture is methyl nitrate. It is an ester of methanol and nitric acid.

They are all different compounds.

Nitromethane.jpg - 2kB Nitromethanol.jpg - 10kB Methyl Nitrate.jpg - 3kB



[Edited on 24-8-2011 by redox]

hissingnoise - 24-8-2011 at 08:05

The name nitromethanol is incorrect as a nitro group (NO<sub>2</sub>;) cannot be attached to an alcohol . . .
Methyl nitrate (CH<sub>3</sub>NO<sub>3</sub>;) is prepared by nitrating methanol - in nitromethane (CH<sub>3</sub>NO<sub>2</sub>;), a hydrogen of methane is replaced by a nitro group!



redox - 24-8-2011 at 08:09

How come a nitro group cannot be on an alcohol?

hissingnoise - 24-8-2011 at 08:15

Because alcohols contain an hydroxyl group . . .
When hydrogen is replaced by nitro, the oxygen remains and a nitrate is formed!


redox - 24-8-2011 at 08:20

Well, yeah, but does nitromethanol exist? Can a nitro group be on the same carbon as a hydroxyl? I have never heard of such a compound.

hissingnoise - 24-8-2011 at 08:24

Nitromethanol is simply a beginner's name for methyl nitrate . . .


redox - 24-8-2011 at 08:47

No, No, that's not what I mean. I know that a nitro group on an oxygen is then nitrate. I'm asking if such a compound exists where a hydroxyl group (OH) is on the same CARBON as a nitro group (NO2). I have never seen or heard of such a compound, but I don't see why it couldn't exist.



This picture illustrates what I am asking about.

[Edited on 24-8-2011 by redox]

Nitroalcohol.jpg - 6kB

HellstormOP - 24-8-2011 at 10:09

Well, if you can find a way to attach a hydroxy group to a carbon atom with a nitro group on it, of course without decomposing the nitro group, then you will have a such compound. But I know no way how that could be accomplished.

[Edited on 24-8-2011 by HellstormOP]

AndersHoveland - 24-8-2011 at 12:59

It is essentially not possible for both a nitro group and a hydroxyl group to be on the same carbon atom.
Basically what would happen is the hydrogen atom in the hydroxyl group would ionize off. Then the electron in the oxygen atom would migrate into the nitro group.
The nitro group would break off as a nitrite ion, leaving an aldehyde behind. This is assuming the pH is basic. Otherwise, the nitrous acid will oxidize the aldehyde to a carboxylic acid.

CH3-CH(NO2)OH --> CH3-CH(NO2)-O[-] H[+] --> CH3-CH=O NO2[-] H[+]

For a similar reason, chlorine atoms cannot exist on the same carbon atom as an amine group.

Although methyl nitrate is structurally similar to nitromethane, the chemical reactivity of the two compounds is quite different.
Nitromethane can undergo complex reactions in acidic or alkaline solutions. The reactions are really quite complicated, and depend on whether water is present, or require strong heating. The reactions of nitromethane are really quite useful, but also rather obscure. Such useful products as hydroxylamine or 2-nitroethanaloxime HON=CHCH2NO2, can result from such reactions.

In terms of chemical reactivity, methyl nitrate generally behaves like any other ester. It will hydrolse back to methanol in the presence of a strong base or acid.

Dinitromethane exists, but methyl dinitrate is extremely unstable and does not exist at room temperature.

[Edited on 24-8-2011 by AndersHoveland]

Satan - 24-8-2011 at 13:11

Quote: Originally posted by HellstormOP  
Well, if you can find a way to attach a hydroxy group to a carbon atom with a nitro group on it, of course without decomposing the nitro group, then you will have a such compound. But I know no way how that could be accomplished.

[Edited on 24-8-2011 by HellstormOP]

Hello Captain obvious :D

Some info on "nitrometanol":
CA Index Name: Methanol, nitro-, radical ion(1-) (9CI)
Class Identifier: Radical Ion

also:
Pulse radiolytic studies of MeNO2 in alk. aq. solns. satd. with N2O show that hydroxyl radicals react rapidly with nitromethane anions. The reaction proceeds by addn. to the C:N bond producing the transient hydroxynitromethane anion radical, i.e., OH.bul. + CH2:NO2- > CH2OHN.bul.O2-.
Source: Journal of Physical Chemistry (1968), 72(10), 3382-7


MeSynth - 25-8-2011 at 12:00

It's called wikipedia . . . chemicalbook . . . google . . .