fivecommandments - special cases like opening of epoxides,...

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CHEMISTRY 236: Fundamental Organic Chemistry I Prof. Scott K. Silverman Spring 2006 University of Illinois at Urbana–Champaign The Five Commandments of Organic Chemistry (as received by Prof. Silverman) 1. Primary carbocations are too unstable to form in solution under normal circumstances. Therefore: Thou shalt not draw a primary carbocation as a discrete intermediate in any of thine reaction mechanisms . 2. Two-electron arrows always originate FROM where the electrons are starting TO where they are going. Therefore: Thou shalt not draw a two-electron arrow starting from H + (proton), which hath but zero electrons; the arrow can proceedeth only towards H + . 3. In order to proceed, substitution or elimination reactions need a good leaving group (or in
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Unformatted text preview: special cases like opening of epoxides, relief of strain). Therefore: Thou shalt not draw a substitution or elimination reaction without a leaving group. 4. Carbon is able to form only four bonds at any given time. Therefore: Thou shalt not draw any organic structure that hath five bonds to carbon at the same time (or even worse, hath more than five). 5. In basic solution, the concentration of H + is necessarily very low, and in acidic solution, the concentration of HO – is necessarily low. Therefore: Thou shalt not invoke the participation of H + in a mechanism operating in basic conditions, and likewise thou shalt not invoke the participation of HO – in a mechanism operating in acidic conditions. 1...
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This note was uploaded on 12/30/2011 for the course CHEM 236 taught by Professor Baranger during the Spring '08 term at University of Illinois at Urbana–Champaign.

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