directing groups

in the molecule 4-methylphenol, both methyl and OH are o/p directors, since both para positions are occupied does it depend which one is the most donating? So would it be most reactive at the ortho position relative to OH?

Original post by jacksonmeg

in the molecule 4-methylphenol, both methyl and OH are o/p directors, since both para positions are occupied does it depend which one is the most donating? So would it be most reactive at the ortho position relative to OH?

yes, in general the +M effect (-OH) tends to be more powerful than the +I effect (-CH3)

Reply 2

username986184

3

Original post by jacksonmeg

in the molecule 4-methylphenol, both methyl and OH are o/p directors, since both para positions are occupied does it depend which one is the most donating? So would it be most reactive at the ortho position relative to OH?

Yes. The phenol donates electrons to the ring mesomerically. This is more strongly activating than the solely inductive electron donating effect of the methyl group.

Reply 3

jacksonmeg

OP

11

thanks for answering

I have one more question if thats ok

I have benzene ring with a CN on position 1, NO2 on position 3, and an aldehyde group on position 5
all 3 are electron withdrawing and are so meta directing, but all meta positions are occupied, does this mean the molecule can't react? or could a group be displaced?

Reply 4

username986184

3

Original post by jacksonmeg

thanks for answering

I have one more question if thats ok

I have benzene ring with a CN on position 1, NO2 on position 3, and an aldehyde group on position 5
all 3 are electron withdrawing and are so meta directing, but all meta positions are occupied, does this mean the molecule can't react? or could a group be displaced?