[thetada]

Hi,

I'm wondering if you could tailor your book recommendations for a specific need of mine. I'm a chemistry teacher, of 16 to 18 year old students, and I'm looking for a text that gives an overview of organic synthesis. To give you an example, some students just argued with me over the sequence of modifications to a starting material in a particular problem (shown below). I had to fluster up the least lame paraphrase that came to mind for: "Well that's what the book says so do it that way." So now I need to brush up on my organic synthesis, and, if you or any other members are aware of such a text, it would be good if it had some rules of thumb about the sensible order in which to do each step, so as not to promote undesirable side reactions.

The problem: They had to get from 3-chloropropanal to 3-aminopropan-1-ol. The book said to first reduce the aldehyde and then substitute the chlorine for the amine group. One student argued that the steps should be in reverse, as he felt that ammonia would react with both the chlorine and the alcohol group. (Interestingly, he was convinced that the ammonia and the alcohol would create an ammonium alkoxide, which I found very unlikely.)

Any takers on either a good text book or some useful wisdom to share with the student would be gratefully received.

Thanks!
 

[kriggy]

Well amine will not form an alkoxide but it will react rapidly with carbonyl group to form an imide. Why you didnt let him do the reaction and see the result? Maybe it could be done that way (I dont think so but hey, its science)

I know several books but Im not sure if they are fit for you: I liked McMurry but lot of ppl actualy prefer Claiden or Kleiden but I have no experience with later. I think those are good for explaining some "basic" reactions and concepts. Then there are Carey or March advanced organic chemistry or the one I realy like: Disconection approach by Warren, however disconection approach is more about general way of designing synthesis - order of events or how to disconect the molecule into smaller pieces - than about it being a list of reactions and their mechanism

[thetada]

I have to say that the disconnection approach looks like exactly what I'm after, thanks! Also, your advice on the specific problem was good (because it supports my opinion :-). Seriously, I wish I could have let the student just go ahead and try it out. Mind you, we're only at high school level so I don't know if the point could be proven either way without a spectroscope.

[kriggy]

That is good point. Maybe different color of product? Or you could try paper chromatography / TLC if you have the needed stuff

[thetada]

This is rapidly turning into the plan for next lesson! TLC is very relevant to their syllabus. If I do it, I'll let you know how it went. Cheers for the input.

[clarkstill]

... it will react rapidly with carbonyl group to form an imide. Why you didnt let him do the reaction and see the result? Maybe it could be done that way (I dont think so but hey, its science)

Just to avoid confusion I think Kriggy mis-typed - he means an imine!