11 - Recitation 8 Notes E2

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The City College of New York, CUNY**We aren't endorsed by this school

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CHEM 26100

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Chemistry

Date

Dec 19, 2024

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SNI + E|] Rxns Fovmation of- C+ . — REARRANGEUE Elimination [sVbstitviion cak B/nve. = ---fi CH;CH>OH E , _— 30°C

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@‘ W e “Y @ H;),L_o’_ CHs),COH - D) izH;; THF _—> / Haa,;,Na .

AT KkENn Reactioh ¢ CH.8 Rxns| Rearrangement ? @ [EV T 4L ) fi / k e ine- H i1 X 1 Lo Hf L J o B 7 i \/// ) ) >, C wovesfo > evbst f_’i: h 4l kere >.’A/ ./7 >’< r~\ ler) SubsT )? KOR 1 //of/oxzm Vi 1 B gl a2 1 ol o gt ® e v i 50 \ ; i Al keeihi A o St Aol 1 @ s of Jo# /\ e /4/@0/,( : 0;“”” At Ao mevedrad7s 4 | St "y(Mc)g/ 1.0 \ N | 2z ) Nag H q i ,, 4 ; NE S ariole Wl gSt ey b Ot yraked oh 2 01TPs i o Al iohol L/ © Hyorosoratin gyl / R DB THE /\/0,»/- \/\A S NG i N gy Wavk N L ,,6;7:-; 2 o o dc Wi 1 @ ; 1end Lubst E /[ - /\\\/ il o NG 353 res . R~ Al | 0 ’ - ' | R (2 / /4, a ,/ A e wns confont. ) | /!ﬂ/{ymri//’w 2 AT [ K/_; o ) L8 CT Z i > gatints el S i3 q9 £y '!; A . | e d by Ly 5 ' Y ¥ 7 v E | CLlgT Py ® nt-a /",/f//;x///w//fw/ AN were | i X | . RLGH P Ty q /YJ % ,’ / > </ B i {7 ° N ' o otl \ o MR P 2 — Carty e Bl e ON YOUR EXAM ' - Addition Reaction of Alkenes AL DMCHA J o DA Reaction Name Reagent Product Notes r‘\ ﬂ p > : ’»' ONLY MCPBA = { , Hydrohalogenation HX (X=Br, Cl,I) Addition of H and X Markovnikov/Rearran s @ 30 A= /4 ox( - emel g 0H Hydrohalogenation ~HBr/ROOR Addition of H and Br Anti-Markovnikov @ C)’( NNdi b ud 1ox Jatse Acid-catalyzed H,0/H,S0, Addition of H and OH Markovnikov/Rearran iy A AL hydration gement possible % Oxymercuration- 1) Hg(OAc),, H,0 Addition of H and OH Markovnikov TR 0G0 y b oH Demercuration 2) NaBH, | / )b Hydroboration- 1) BH,.THF Addition of H and OH Anti- 7 2) NatS0s N Oxidation 2) H,0,, OH Markovnikov/Syn addition Catalytic H,/Pt the addition of H, acrossa Syn addition @ C 40 hydrogenation C=C double bond Xtaat, L G s Halogenation X, (X=Br,CLI)in addition of two halogen Anti addition ) / CCl, atoms across a C=C double - i % O > (9 bond ; g \% G e \/\ Anti Dihydroxylation 1) MCPBA addition of OH and OH Anti addition 2)H,0" across a C=C double bond / Syn Dihydroxylation 1) OsO, addition of OH and OH Syn addition 77 / ¥ 2) NaHSO, across a C=C double bond Gl P >// \ Oxidative Cleavage 1) O, Aldehydes/ketones e 2) DMS i« NaKe o AlCO [ (/‘3

15. (10 pts) Propose a detailed, stepwise mechanism for the following transformation: (Use curved arrows to show movement of electrons) H;0" — H20