Originally posted by rogue chemist
I am not going to do them for you but I will give you the necessary info to solve them.
First: Benzoic acid has an acidic proton, what compound in that list would react with an acidic proton to make an obvious result?
Second: Iodine is a pretty good leaving group, so there will be a sort of equilibrium between the iodooctane and the positive carbocation of
octane(carbocation in the spot iodine was removed from) Furthermore, iodines ability as a leaving group is enhanced by the fact that the iodine is on
a secondary carbon. Think SN1. So if another iodide ion were to come in at the carbocation, what would be the result?
Third: Again SN1 type mech this time leaving a tertiary carbocation, much more stable than primary or secondary. Now any lone pair on a molecule will
get sucked over to that carbocation. Which two things in that list are a result of a lone pair going at the carbocation? Product will likely be a mix
of two things there, but you must consider the groups attached to the atom with the lone pair on it, the one which is electron donating will increase
the negative charge on the atom with lone pair and preferentially react with the carbocation. |