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Chapter 9 Suggested solutions for Chapter 9 Purpose of the problem Product prediction in a more complicated case and logical extension to a new situation. agested solution reagent must be formed from the alkyl bromide and this must add to the ketone. acidic work-up (not mentioned in the question as is often the case) now gives a tertiary that must be biperidine. Br 1. Mg, MgBr 0 N N stable biperidin To get procyclidine we need to change both the alkyl halide and the ketone, but the reaction is similar. 0 Br MgBr 1. Mg, + N N procyclidine Problem 11 Though heterocyclic compounds, such as the nitrogen ring system in this question, are troduced rather later in this book, use your knowledge of Grignard chemistry to draw a for what happens here. It is important that you prove to yourself that you can mechanisms for reactions on compounds that you have never met before. CI Me 1. Mg, N 2. Me MeO + MeO N Purpose of the problem to prove that the reactions that didn't happen in Problem 9 can actually take place if there's no competition. Suggested solution Though this is chemistry you've not seen, the mere structure of the product tells you what happens - the alkyl (benzylic actually) chloride forms a Grignard reagent and this adds to Note that + charge - it makes all the difference as to how electrophilic a C=N group might be. CI Me Me N N 1. Mg, MeO MeO MeO