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CHEM 2331H
T.Andrew Taton

Honors OChem Exam 4 Study Guide More substituted alcohols = less acidic…except phenols, which = pretty acidic carbanion stabilities Forming alkoxide ions (strong nucleophiles and bases) Alcohol + Metal (Na or K) alkoxide ion + H 2 Use Na for primary and more acidic alcohols (methanol and ethanol = more reactive), use K (more reactive) for secondary/tertiary *For phenol: Phenol + NaOH or KOH  phenoxide + water (b/c phenol = acidic enough to neutralize base) NucleophilicAdditions to Carbonyls (all done in ethers) (p. 450) Generating Organometallic Reagents (equivalent to carbanions) 1* Deprotonation (not common, doesn’t work for sp (b/c alkanes aren’t acidic enough), works for alkynyl and some sp ) 2 2* Metalation of an alkyl halide: common for Grignard reagents, sp alkylithiums and all others too (p. 443) I = most reactive, F = least, terrible Make Grignard reagent in dry (anhydrous) ether solvent For Li addition, use hexane for Br, pentane for Cl, ether for bromobenzene 2 3 3* Lithium-halogen exchange: common for sp alkyllithiums, not useful for sp alkylithiums (see practice exam for mechanism) Rxn of alkylmetals w/ C=O bonds (p. 444) DoubleAddition ofAlkylmetals to Esters andAcyl Halides (p. 447) Adds twice b/c ketones and aldehydes = more electrophilic than esters and acyl halides (see exam for mechanism for first one) Oxidation: Losing H , adding O or O 2 2 - Reduction: Losing O o2 O, adding H or2H; Neither:Add/lose H , H O2 or HX  Reduce alkyl halide alkane by (alkyl halide organometallic reagent react w/ water  alkane) (can protonate w/ O-H, N-H, S-H, and –C=C-H….basically with any acid…organometallic thing attacks the H) (organometallic can also attack C, S, or N in C=O, C=N, C=N, S=O, N=O) Sodium borohydride or lithium aluminum hydride = better nucleophiles than bases Normal hydride attacks happen in ether…?? Do we need to know Collins/Jones reagent (p. 472) and other crap from that section besides swern oxidation? *Generally for oxidation, primary aldehyde, secondary ketone ←←←←←←←Oxidation←←←←←←←← DMP under mild conditions (room T, neutral pH) PrimaryAlcohols: KMnO or H4O 3 Secondary alcohols: KMnO or 4NO 3 Does nothing w/ tertiary Swern Oxidation (PCC = toxic reagent that does same thing along w/ CH Cl ) 2 2 Carboxylic acid or aldeh yde
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