[Help]nitration of methyl benzoate

[phagocytes]

How do the conditions for nitration of methyl benzoate differ from those for the nitration of benzene?

 

 

what is the mechanism nitration of methyl benzoate to form methyl 3-nitrobenzoate?

 

Thanks.

[Invader_Gir]

I'm fairly sure that only a few reaction conditions need to be modified. Methyl Benzoate consists of a benzene ring with an electron withdrawing carbonyl group attached. This being the case, an elevated temperature and a higher concentration of the electrophile should work. Substitution would also occur primarily meta to the carbonyl group.

 

If multiple nitrations are required, an even higher temperature and concentration would be needed, since there is an electron withdrawing nitro group present on the ring aswell. Again that substitution would occur meta to both the carboxyl group and the existing nitro group. Hope this helps.

[phagocytes]

Thanks a lot!

[ecoli]

I'm fairly sure that only a few reaction conditions need to be modified. Methyl Benzoate consists of a benzene ring with an electron withdrawing carbonyl group attached.

NO NO NO!

 

Methyl Benzoate is a benzene ring with a carboxylic acid group attached. http://en.wikipedia.org/wiki/Methyl_benzoate

 

And thus, you have to consider the withdrawing affects when nitrating.

 

http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/carey04oc/ref/ch12substituenteffects.html

 

Since the COOH group is meta directing, there is only one carbon in which the NO2 group will be added.

 

the mechanism will look like this:

 

[Invader_Gir]

No need to get snippy.

 

It isn't a carboxylic acid group either. It's an ester, that is why I said carbonyl, similar but not the same. I did take into account the electron withdrawing effects. Also, there are two equivalent meta positions, and once the first nitro group is attached, nitration may happen again at the second meta position, ie, carbon 5.

[ecoli]

No need to get snippy.

I didn't mean to sound snippy. lol.

 

It isn't a carboxylic acid group either. It's an ester, that is why I said carbonyl, similar but not the same.

stupid me... that's what I meant to say.

 

I did take into account the electron withdrawing effects. Also, there are two equivalent meta positions, and once the first nitro group is attached, nitration may happen again at the second meta position, ie, carbon 5.

hm... that's true, but since the ester group is also deactivating, couldn't you stop the reaction before this took place?

[Invader_Gir]

No harm no foul.

 

hm... that's true, but since the ester group is also deactivating, couldn't you stop the reaction before this took place?

 

Oh yes. In order to get the second nitration, higher temps, longer reaction times, would be required.

[ecoli]

OK... we're on the same page now.

[phagocytes]

NO NO NO!

 

Methyl Benzoate is a benzene ring with a carboxylic acid group attached. http://en.wikipedia.org/wiki/Methyl_benzoate

 

And thus, you have to consider the withdrawing affects when nitrating.

 

http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/carey04oc/ref/ch12substituenteffects.html

 

Since the COOH group is meta directing, there is only one carbon in which the NO2 group will be added.

 

the mechanism will look like this:

 

 

i see

Thanks!