What would be the directing effects of a –CH3 (a donating group) / of a carboxylic acid (an electron withdrawing group)?

Question

Different functional groups are said to “direct” nitration to different locations on a benzene ring. What would be the directing effects of a –CH3 (a donating group) / of a carboxylic acid (an electron withdrawing group)?

Answer 1

Hello Amber

 

Electron donating groups such as -CH₃ will direct substituents to the ortho (Carbon #2) and para (Carbon #4) positions on the benzene ring. 

 

A benzene ring with a -CH₃on it is called toluene. Nitration of toluene will form a mixture of 2 products, ortho-nitrotoluene (2-nitrotoluene) and para-nitrotoluene (4-nitrotoluene).

 

Electron withdrawing groups such as -COOH will direct substituents to the meta (Carbon #3) position on the benzene ring. 

 

A benzene ring with a -COOH on it is called benzoic acid. Nitration of benzoic acid will form only one product, meta-nitrobenzoic acid (3-nitrobenzoic acid).