Question

1. What product (or products) may form if the reaction is not kept on ice during the addition of the acid mixture to the acetanilide?

2. If compound A is more polar than compound B, which compound will have the highest Rf value on a TLC plate that is eluted with ethyl acetate? Which compound will have the highest Rf value if the plate is eluted with dichloromethane?

3. What compound (or compounds) would form if aniline was used instead of acetanilide?

Please help on these questions.

Answer 1

1)the acetanilide has a moderately strong activating anilide functional group,if not kept at a cool temperature,di-nitro substituted product is possible

2) compound B will have the highest Rf , value when eluted with ethyl acetate because it is less polar so move further on the polar silica gel surface.compound B still have highest Rf valve when the plate is eluated with dichloromethane.Dichlorometane is slightly less polar than ethyl acetate,but still polar enough to be widely used solvent for TLC analysis

3) Aniline is avery strong ortho-para director and is strong,in fact that is tends to continue reaction untill all orthopaedic and para positionos are full. this means that is a chance that could be 4 different isomers formed in the reaction.