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Notes - xx Competition i—PrBr NaOEt 9 CH30H=CH2(87...

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Unformatted text preview: xx Competition i—PrBr + NaOEt 9 CH30H=CH2 (87%) l—PrOEt (13%) PrBr + NaOEt 9 CH30H=CH2 (9%) PrOEt (91%) 8.11, F8.7, T8.9 Summary of reactivity: $31, 852, E1, 132* 1. Good Leaving Group OTf> OTs > I > Br> H20> Cl 2. Substrate: a) Aryl b) Me, Good Nucleophile (8.5, T8.4) 3. Strong Base (5.12-5.17, 8.11) No: NR ‘ (8.2, 8.12, T83) (8.4, 8.7) NR 8N2 E2 a. 2°, 3° R3C- > R2N— > R0- b. 1° R30- > LDA > t-BuO‘ (strong bulky base) 4. No Strong Base (eg. RS—, l-, CN-, NH3,, Br—) a. 1° 8N2 b. 3° (8.7) 8N1 0. 2° (8.10) i. polar aprotic solvent 3N2 ii. polar protic solvent 8N1 Will substitution or elimination occur? RCing {primary RfiiiX (secondary) RC)”; (_ tertiary) llalide type Highly favored Does not occur Can occur with Occurs in Can occur with benzylic and allylic halides Favored in hydroxylic competition with E2 benzylic and aliylic halides reaction Does not occur Occurs in solvents competition with SNl reaction *McMurry Organic chemistry 4th edition Occurs when strong bases are used Favored when strong bases are used Favored when bases are used ...
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