[schowder94]

Hello everyone. This is my first time posting on this website. I am extremly terrible at organic chemistry. I have an exam coming up in a day and I need some help on completeing these last review questions before the exam. I am not sure about any of the products or if I am doing the problem correctly. I would like some help in checking if my solution is correct and perhaps helping me in finding the others if possible. The problems are:

[Borek]

Benzonitrile is just

[Meter]

Why not halogenation followed by NAS with cyanide?

[Babcock_Hall]

Regarding the hydration of an alkyne, you have conjured up an R group from somewhere, and it has confused the regiochemical issue.  I agree that tautomerization is part of the correct mechanism.

[Babcock_Hall]

I am also unsure why you chose diethyl phosphite in preference to a different phosphite.

[rolnor]

I am also unsure why you chose diethyl phosphite in preference to a different phosphite.

Before the Arbuzove reaction wich use triethylphosphite or similar, people use diethylphosphite and base as I recall. The Arbuzov is better I believe.
This is the other one:
https://en.m.wikipedia.org/wiki/Michaelis%E2%80%93Becker_reaction

[Babcock_Hall]

I have done both Michaelis-Arbuzov and Michaelis-Becker reactions, and there are some advantages to the Michaelis-Becker way, in terms of side products.  However, one does need a very strong base.

[rolnor]

The by-product from Arbuzov is most often a gas at the reaction-temp. ?

[Babcock_Hall]

Yes, the volatility works in one's favor, but I have seen small amounts of the impurity associated with alkylation of the by-product in the past.