I was wondering if someone could help me find references available that will help me solve the following problems. These are not homework problems, but are suggested problems that were given to me by my instructor.

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I'm specifically interested in learning how to solve question A. (b). How can I know whether a reaction will occur between the two products and further, how can I predict what the product will be if a reaction does occur (what atoms bond together, and how can I know which atoms bond together in any organic reaction)?


Concerning your first question: I found that the book "Organic Chemistry" by Clayden, Warren, Wothers and Greeves and here especially the 8th chapter contains a very good and readable introduction to acidity and basicity. After you have worked through this chapter you should be able to explain why certain molecules are as basic/acidic as they are and you see a lot of typical $\mathrm{p}K_{\mathrm{a}}$ values for a lot of substance classes so that you get some knowledge about what $\mathrm{p}K_{\mathrm{a}}$ values you can expect for other substances. As for your second question: If you want to know why reactions occur in the way they do you'll have to take courses in Organic Chemistry. Apart from that, I wholeheartedly recommend the aforementioned book again. If you work through this book (this will take you a while: it has 1200 pages... but then again, that is 1200 very readable pages :)) you'll have a very solid basis in organic reaction mechanisms and organic chemistry in general. If you want to dig a little deeper this book by Bruckner is very thorough but a little dry.

One particular perspective that I found very helpful in explaining why reactions happen in the way they do was the frontier orbital theory. A very good and readable book about its use in organic chemistry is this one by Fleming. The book by Clayden et al. also uses this theory a lot in explaining reaction mechanisms.

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    $\begingroup$ +1, I echo your sentiments re: the Clayden, et al. and (especially) Fleming books. The latter is really excellent in dealing with an intrinsically abstruse subject. On the introductory level, I think Klein's Organic Chemistry is also fairly good, though a bit handwavy w/r/t certain complexities, and with disappointingly meager coverage of MO theory. At a higher level, I thought Carey & Sundberg's two-volume Advanced Organic Chemistry was highly instructive and lucid. $\endgroup$ – Greg E. Dec 25 '13 at 19:58

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