CHEM 140A Study Guide - Final Guide: Methanol, Reaction Rate, Acetonitrile
31 May 2016
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2n + 2 - m - x + y. Nh3 35 h2n increasing acidity increasing leaving ability increasing basicity/nucleophilicity increasing nucleophilicity (protic) Sn2: inversion of con guration, 1>2 (steric hindrance), need good leaving group & nucleophile, aprotic solvent. Sn1: 3>2 (carbocation is stabilized w/ hyperconjugation), carbocation is planar (achiral) so product is racemic, need excellent leaving group & all nucleophiles work, protic solvent. Protic solvents (h-bond): weaken the ability of nu to attack. as the solvated ion becomes larger, the salvation is diminished. E1: excellent leaving group & all nucleophiles work, protic solvent that is non- nucleophilic (tertiary butanol), only 3>2. E2: a good leaving group and a strong base are needed. Bulky bases do not act as nucleophiles so prevent sn2, aprotic solvent. Rmgbr. he presence of x increases acidity as inductive efect stabilizes the alkoxide. Alcohols are produced from aldehydes (anal) and ketones (anone) by hyride reduction (na+-bh4/ch3oh, li+-alh4/ether) and organometallic reduction.
