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SCAN0002 - Practice 15 Substitution and Elimination 2 1...

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Unformatted text preview: Practice 15 - Substitution and Elimination 2 1. Provide the products, reagents or starting materials needed for the following reactions, show all stereochemistg. 2. Identify whether the reaction goes by an $42 or an SNl mechanism. N 1 Mai 1W 8 W\ S 2 a) War Tefine I N I) \i/ FizU W 6N1 (resonance) 9i OH : H 0 b) \/\Br NaSH \ASH 3N2 j) ©/\ _2_.. 3N1 Br CN H 1 CN NaBr NaBr d) O—ors T_"ttom .le O—Br 5.2 I) Q W2 5N1 Cl Br NaBr 5N1 o< Nai O< e) _Fl'U"" m ————-> 3N1 OTs 2 Br ) CI H20 1 0T]c Nai - NaBr f) O‘Br m 0'1 5"? (achiral) ”) \A/Y aoeionltril BM 3N2 OTf H O MeOH Bi' 0H Br OCH-3‘ NaBr ) /\/\/\ NaH H20 9 HO Br _..__. OTf 3. Give the indicated rankings for the following. Provide ex lainations for ur rankin s a) Fastest 5N2 reaction with Nal in acetone e) Fastest 8N1 reaction Br \Jx—rafi N31 eI\/L \/LN W \t 04, a, We W I 1 2 3 1 Least Hindered Polar Protic Solvent b) Fastest 8N1 reaction with Nai in water fl fastest SN1 reaction Br Br N 1 Br \/\ C7< 3‘ Nal Br \/K Br W W 3 2 1 1 2 Most Stable Carbocation Resonance c) fastest 8N2 reaction 9) fastest reaction with NaSH V\ Nal \/L \A Br me V\l \/‘BrN "rem V\1 Cl Br I 1 2 3 2 1 Polar Solvent Best Leaving Group d) best solvent for a 8N2 reaction 9) best Nucleophile NaCN NaOH NaBr 0 V\OH O 1 3 2 )k/ Least Hindered More Polarizable 2 h best nucleo hile Polar Polar Non-polar ) :1 Nat NaBr NaF Protic Aprotic 1 2 3 More Polarizable ...
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