What Are the Major Products of Benzoic Acid and Hydroquinone Nitration?

[jkh4]

Homework Statement

1) What other nitration products in a electrophilic nitration of benzoic acid would be formed if each reaction were carried out at a higher temperature?

2) The nitration of hydroquinone leads to a low yield of nitrohydroquinone. Propose the structure of the major product: HINT: nitric acid can also function as an oxidizing agent.

Homework Equations

The Attempt at a Solution

Please correct me if I am wrong.
For #1: I think since it is at higher temperature, and benzoic acid is a meta director, the both meta position of the benzene ring will have NO2 attached to it so it will be a 3,5 - dinitro product.

For #2: I was thinking the structure of hydroquinone is [PLAIN]http://en.wikipedia.org/wiki/Image:Hydroquinone.svg.[/URL] Since it has two hydroxide attached and they are all ortho/para director, i think the NO2 will be attached to all four remaining positions.

Can someone please help me out? Thanks.

 

[chemisttree]

For #2: I was thinking the structure of hydroquinone is [PLAIN]http://en.wikipedia.org/wiki/Image:Hydroquinone.svg.[/URL] Since it has two hydroxide attached and they are all ortho/para director, i think the NO2 will be attached to all four remaining positions.

Can someone please help me out? Thanks.

The hint said that nitric acid can also act as an oxidant. How might you use this hint?

 

[Blueshift5]

Your explanation for #1 is correct. At higher temperatures, the meta positions will become more reactive due to increased delocalization of the negative charge on the ring.

For #2, you are correct that hydroquinone is a strong reducing agent and can be oxidized by nitric acid to form nitrohydroquinone. The major product would be 2,5-dinitrohydroquinone, as both ortho positions are more reactive due to the presence of the hydroxyl groups. This product is also stabilized by resonance effects.