Seeking orgo 2 hw assistance

[Brawwp]

I'm new to the forum, and believe it or not, I love organic chemistry. I'm not the best at it, but I really enjoy the subject. That said, we were given a homework assignment with 5 questions (due later tomorrow), and we are allowed to use any resources we want. Well, there are about 2 of the 5 that I just have no clue for, and for the other 3 I was hoping to have my work checked. 3 synthesis, 1 predict the acidity from values in a table, 1 predict the acidity between 3 cyclic compounds.

 

Can anyone on here help me? I'd be willing to even possibly paypal money for the help. I am not just asking for answers, but assistance for me to get the correct answer. This counts as a big portion of my overall, and will help for our upcoming exam to have the correct answers. If you are willing, maybe we can text each other or Facebook message for faster communication? I'd really appreciate it. I'll be sure to hang around on this site and spread the help whenever I can.

[hypervalent_iodine]

You're more than welcome to post the questions. Members won't answer them directly, but we can help point you in the right direction and check your working.

[Brawwp]

Ok, I have attached 2 synthesis problems I tried. Are these correct?

 

For the the ones with nbs, would #1 only form the thermo product since it is easiest to form, and the most stable product, or would it still produce both products?

[hypervalent_iodine]

You need to have another look at the first one. I assume you were attempting to show a [4+2] pericyclic reaction, but your reagents aren't quite right for what you've shown and if you follow your arrows, you'll see you're missing some things. Try doing some retrosynthetic analysis and then work forwards. If you have Clayden, it has a very nice chapter on how to go about doing retrosynthetic analyses.

 

At a quick glance, the first radical sequence you have going from cyclopentane to cyclopentene looks fine. I would possibly question whether or not you would get the second addition/elimination happening to give you cyclopentadiene, but I am inexperienced in these types of radical reactions so this may not be an issue. It's not really clear what the question is here also; do you need to start from cyclopentane? The DA reaction in this one looks fine, except I would make your arrows flow in the other direction to represent the electron rich/deficient ends of the molecule.

 

It is possible that you get the other product in (1), but you probably wouldn't get very much of it since, as you noted, it is both less stable and the slower of the two to form. I would still note it in your answer, but maybe add a small paragraph explaining why you don't think you would get it in appreciable quantities.