6 truths of organic chemistry
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1) Approach unknown reactions just like you should approach all reactions
– Identify nucleophile(s) – Identify electrophile(s) – Nucleophiles attack electrophiles – Repeat
2) Weaker Acid Wins
– In and acid/base equilibrium, the equilibrium favors the side of the arrow with the weaker acid (the compound with the higher pKa)
3) Mind your charges
– Make sure the net charge of all compounds is consistent throughout a mechanism
4) The 2nd Best Rule
– The 2nd best resonance structure usually defines a functional group’s reactivity
5) When in doubt: Number Your Carbons & draw out hidden hydrogens!
– When coupling 2 molecules, if it not readily obvious where the various atoms go in the product, number the carbon atoms in the starting material and map those numbers on to the product. -Also, draw out hidden hydrogens at the reaction site
6) Carbonyls: THE CODE
– There are only 3 elementary steps in a carbonyl addition mechanism. 1) Proton Transfer (always reversible) 2) Nucleophilic Addition to a Carbonyl (electrons go up onto oxygen) 3) Electrons Collapse Down from Oxygen (and kick out a good leaving group) The steps can be in any order and repeated, but those are the only 3 steps needed for addition to acid chlorides, acid anhydrides, aldehydes, ketones, amides, esters, and carboxylic acids (including aldol and Claisen reaction