Chem 350 final exam reactions 1

Chem 350 final exam reactions 1 - Generic React ions LG R...

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R LG Nuc R Nuc R OH TsCl R OTs R NaNH 2 R 1 -X H 2 Pt R R NaNH 2 X R R NaNH 2 X H 2 R Na NH 3 H 2 SO 4 R O HgSO 4, H 2 O R Br 2 , hv Na Na 2 Cr 2 O 7 G e n e r i c R e a c t i o n s M e c h a n i s m D e t a i l s (S = stereo R = regio) S N 2 (required) S N 2 like Acid/Base (required) E2 (required) E2 (required) Concerted Radical Carbocation (required) Concerted(required) Concerted S N 2 Me > 1 o > 2 o LG = leaving group S = S N 2 inversion Nuc = nucleophile Turns alcohols into leaving groups S = retention Deprotonates terminal alkynes Strong Base required S N 2: Me > 1 o E2: 3 o > 2 o S = S N 2inversion Reduces alkenes, alkynes, aromatics to alkanes S = Syn addition (cis products) S = Anti addition (trans products) R = Mark's rule enol to keto tautomerization R = Mark's rule R = Mark's rule Allyic bromination S = random R = dependant on substitution
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Unformatted text preview: S = retention S = Zaitsev's rule Benzylic oxidation Requires 1 benzylic hydrogen pyridine H R Na R R R 1 X R R X R R R R RCH 2 CH 2 R R Lindlar's cat. R R R R R R R R 1 eq. HX R X 2 eq. HX R X X R 1 eq. X 2 R X 2 eq. X 2 R X X X X X R Br (or NBS, ROOR) NH 3 R R H 2 SO 4 R H R O OH S N 2 (required) Concerted Carbocation (required) Carbocation (required) Radical Radical Terminal alkynes required 3 eq. NaNH 2 Strong Base required Terminal alkynes required 3 eq. NaNH 2 Strong Base required Br 2 , hv (or NBS, ROOR) Br Radical Benzylic bromination S = random...
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