[citron2k1]

Please help me answer these questions. I'm not even sure why this question was assigned because I don't recall ever discussing this in class. I don't even know where to begin. I have done some extensive searches on google.com but to no avail. What do I even search? Synthesis of organic compound when heated and cooled? I am desperate now. Any kind of input would be most helpful

Kind Regards,
Michael

[Dan]

This question is about kinetic vs. thermodynamic control. Have a read about it, and have another shot at the question. Post your ideas and we'll help you out from there.

[citron2k1]

Thank you, finally I have somewhere to start. I will get back to you after I read up on this.

[citron2k1]

Ok so for a) I would say that product C would be thermodynamically favored since it is the most stable (lowest energy). And for b) I would say that product A is the most kinetically favored since it is least stable and has the highest energy product. Also being that when the H2O is protonated, it has a lower activation energy to reach the methyl group on the carbocation.

Thoughts?

[Honclbrif]

Don't just think about the product, think about intermediates, or even better, transition state.

[Honclbrif]

I guess what I'm trying to say is consider the entire energy diagram of the reaction. Look up the Curtin-Hammett principle.

[citron2k1]

Do I at least have the correct results for question A & B? Just need to know so that I can come up with the correct explanation for why that is.

Thanks.

[orgopete]

This reminds me of the movie, "My Cousin Vinnie".

Mona Lisa Vito: No, it's a trick question. (IMDB)

This looks like a textbook question. If I were to attempt to do this reaction, I would be surprised if I got anything besides toluene as the product.

For the answer to the problem, I suggest explaining why C is the most stable and why A is the kinetic product. Least or most stable does not seem a good rationale.

[citron2k1]

For the answer to the problem, I suggest explaining why C is the most stable and why A is the kinetic product. Least or most stable does not seem a good rationale.

I do realize I will need to elaborate more on the why, but do I at least have the correct answers for each question A & B?