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SCAN0005 - Practice 15 — Substitution and Elimination 4...

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Unformatted text preview: Practice 15 — Substitution and Elimination 4 Provide the products of the following reactions. Be sure to show all appropriate stereochemislry. Show the correct curved arrow mechanism for all 1 — 12. NaCN 1- WBr acetone DMF KOt-Bu t-BUOH 3. wBr NaNHz acetone NaCN ———> acetone 6. VY Nal acetone 0... Z ~é For the following pairs of reactions predict which will be faster and explain why, 13. a) Y0 £33 YNS b) \[AI YNS NaN; EtOH faster - betler leaving group b) B,- H 0 OH faster — ‘ heat V carbocauon Ph ph more stable Br SH 15 a) W\ NaSH Vl\/\ B b) V\/\/ r NaSH MSH faster- primary 7. KOH W 8. W NaNHZ W TsO ’H DMSO H .Br NaOH G 9. __> H20 “gr 7 10 6 Mel (j -—-—-—————-—> H20 H gr A NaOMe 11. —. MeOH H gr NHZ NH3 12. ———_» 8N2 (achlral) BM: 16. a) \/\ NaCN Br We Fl”. \ACN b) V\B NaCN V\ faster— r CN polar. aprotic solvent faster- both are in a poor SN2 17. a) NaOH \/\ \/\ solvent, but Br H20 0” hydroxide is better nucleophile b) N O CCH 0 a 2 3 m3.- ——~——> V\o/U\ H20 "- 3) \AB NaCN \* T CN b) V\ NaCN faster— Br V\CN primary ...
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