I posted the following question, and I got two downvotes without reason.

Resource for general organic chemistry

I did my research (looked at the whole resource page and browsed books like Solomons and Sykes). I am also pretty clear, I need a book with a thorough explanation of effects and their stabilities.

Can someone explain what might be wrong in the way I posted my question.


1 Answer 1


Firstly I'll give you my answer to your original question.

There isn't going to be a book that gives you firm rules on how to compare different effects and when they dominate. The reason is because there are no such firm rules. Even if you created such a rule, you would have to tabulate all the exceptions, and there are lots of them. And you would need to have exceptions to your exceptions, too.

Why is it so complicated? Well, it's because these things are not exact sciences. It's impossible to compare resonance with inductive effects unless you have one unified scale on which you can compare the two. Such a scale exists in some cases: for example you can indirectly measure their importance in acid-base chemistry using pKa values. However, in general, you can't quantify how much resonance stabilisation there is, or how much inductive withdrawal there is. It's not like having two opposing forces in physics which you can both measure in newtons to see which one is bigger.

Unfortunately, there isn't a shortcut where you can learn 5 golden rules (or 10, or whatever) and have it apply to all of organic chemistry. So, there isn't going to be a book, or a book chapter, which describes such rules. Most sensible books introduce the concepts as and when they are needed, when talking about mechanisms or functional groups or other contexts.

Hence the answer to your question is to read a good organic chemistry book, one which presents material in an organised manner, and not one which throws hundreds of examples and expects you to memorise them for every different compound. My suggestion is Clayden. That is already listed in the resources post. Some of the others are probably too advanced and some of the others too simple.

Now we can have a guess at why your original question is being downvoted, although I didn't downvote it.

There isn't much of a proper answer to give, because the book that you're looking for doesn't really exist. At best we could tell you to look for a proper organic chemistry text, as I did, but those books have already been collected in the resources post.

If you want to ask about "why are there so many exceptions to the rules", then by all means; that's a separate question which is answerable (using e.g. the first part of what I've written). But I'd say to just limit it to one "rule" at a time, e.g. resonance vs inductive effects. Or else that would probably be too broad.

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    $\begingroup$ My guess for one reason why this was downvoted is that it invites opinion-based answers. $\endgroup$ May 6, 2020 at 8:39

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