CHEM 2331H Study Guide - Midterm Guide: Bromobenzene, Stereochemistry, Aldehyde
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More substituted alcohols = less acidic except phenols, which = pretty acidic carbanion stabilities. Alcohol + metal (na or k) alkoxide ion + h2. 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) Nucleophilic additions to carbonyls (all done in ethers) (p. 450) 1* deprotonation (not common, doesn"t work for sp3 (b/c alkanes aren"t acidic enough), works for alkynyl and some sp2) 2* metalation of an alkyl halide: common for grignard reagents, sp3 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. 3* lithium-halogen exchange: common for sp2 alkyllithiums, not useful for sp3 alkylithiums.
