Chapter 6 Week 7 Answers

Chapter 6 Week 7 Answers - Week 6 — Chapter 6 Chem 30A -...

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Unformatted text preview: Week 6 — Chapter 6 Chem 30A - Alkene Reactions Objectives: 1. 2. 3. Learn the basic driving forces of reactions Understand regio/stereoselectivity in reactions Draw and describe reaction mechanisms Driving forces of reactions: There are three main ways to describe the steps of every reaction. 1. Electrostatic effects 2. Sterics 3. Stability Understanding these three ideas can help to understand reactions and why they occur as specified. General Guidelines for studying reactions: 1. Make flashcards! This allows you to carry reactions with you wherever you go so you are constantly exposed to the material. Plus the process of making them will help solidify these ideas Learn the reaction not just in the forward direction, but the backward (retrosynthesis) Try and make your own problems and solve them! Predicting products and outcomes are a great way to learn the reactions inside and out Be able to describe reactions in words: Arrows and structures are arbitrary and difficult to memorize. Plus you probably won’t see the same structure on a test so you need to have a flexible working knowledge. Being able to describe what is happening (proton adds to alkene, followed by... etc etc.) will allow you to apply a reaction to any situation Stereochemistry and regioselectivity are as important as the mechanism itself. These can be inherently determined from the mechanism Don’t wait till last minute to learn these reactions. Try and start a week before the test date to start making study guides. Practice Practice Practice Practice: FIN m “02 LOWS UMJ’V‘ ‘n‘x‘. deemew W \n l‘ _. \ 3' m +LUSOL1 _——7 Q” l U + l7 \l/j‘m V lMaHQDSiHfi) l \ fl 0 P13 Addition of H2: (HZ/Metal + Alkene) Mechanism: \(q; H H H _..—-=7 G) Steps (inwards): Stereochemistry: 3 n motif; (6') “1 41:5 53):; slag?“ Regioselectivity: a H 3 W2 (A V Other considerations: Oxidation by OsO4: ' (OsO4/NaHSO4’,H20 + Alkene) H I m. - 0 am a 9 '9‘ “'3 rgo / \ (5 \hSQ Na? 0”” veg “ CD Steps (in words): _ Stereochemistry: 53%|) CD has max? _ Regioselectivity: (29 (WW LU ’OH - Other considerations: a5 Example Problems: W Jr L0501.‘ / 4+0 so“ -.—-——'> v eukarlwq‘qu "‘0‘" ‘ . ‘ D b Oxidation by Ozone: ' (03I(CH3)ZS+ Alkene) Mechanism: ‘ (9 ® ® @ é.— .-._ _ ' ._ ‘ 8 / /:/ 0 ® G/KO (3:0 {ch—oi $4003? G _ T __ w ., —# + we ~v o a» w iv A“ 7 ~ r. W21 ' W W (h 3;... Q (Q (Moiomulfl) - - Q i I Steps (in words): Stereochemistry: ® oxth M018 wfim n {DJ—1L1 ® MoiDuMCM iwmgfi ‘ @ 3 “QC/Ruhr” 0-K: “MK “A meomlfci |"TMLhOtl'leI considerations: ® Oman {iamw «who 3 ‘3st @ 3(9— car «fit-a xample Problems: (.05 __ .[io m to J, 7 i 3 U 9- (“3&3 I “ 121m}; +113ng - i H. /\/\/ ‘ f/o ”\ ‘2) ~ 0:) Elm“ ozom' ' 1 Regioselectiirity: Oxymercuration-Reduction: (Hg(OAc)2,H20/NaBH4 + Alkene) Mechanism: \svck ML 0k H / A: fl {1 + -—‘7 ' U # 09R F, \J . ,: a 63 (9 "1°" a“; (:9 © Steps (in words): : Stereochemistry: ‘ (Darbmlikdflbfidjf 03417 QM : Q) “)0 7” “A Ad 4%“ WM 5.4,, Mm, Regioselectivity: movkww law (3) [[113 degrfiud“ Other considerations: no ANMAG emu f3 (Eb wen (u’ Fwd (191m mam. Example Problems: 94 HO O/* I:HB(OAL},’I')0 \ * “49%); 0% M ilkiahkrw - d H 7 ’1- MB‘“! 7L’Lfi H J L N"‘"fi ‘ ’ 1.103% K /\( Hydroboration-Oxidation: (BH3/H202,NaOH+ Alkene) cm Mechanism: ‘ "8"2 '1 an @ 0M \é 1 Af/ .4) s \ (D \f“ - (M; a Q) Etepi’fimrdiz: Ad to” L0“! Stereochemistry: 5T6: “’31:” _. 5 0‘ ‘ ‘3 «ML-3 \‘o ‘25s hmdm’l Lu/(‘Dfln Regioselectivity: 0H M {KS "‘1‘- bbwwl gym}; (ch WWWEWJ ) th ‘d t' : v ‘1 mat 0“ Wk mo} (SEQ IPDHVDJ“ O erconSI eramns a With ® 9» * 93 M“ n W Example Problems: LB“; __ s \ Lem, __ / W; ~> g+l.b°w““°“ 7 @ +k‘3finwfl 7 Q‘Wflw““"' /\/ fl 0” cit OHM W M Addition of Bromine and Chlorine: (ClZ/BrZ + Alkene) Mechanism: (9 @ 3 Cl AW J i a). an O we —-—-7 Nil: Steps (in words): Stereochemistry: 0) at& am Jo AWN . m M b Cka meran a?“ Regioselectivity: M CI (141.31» Ml: “L5, Cw .n.'\ @090“; 411 NA su‘a, Guiana Other considerations: MD M F I Example Problems: UJ‘ ch “I‘m/Y + C11 ._.>/%\ In 4 911+) Cb Addition of HOCl and HOBr: (X2/I-120+ Alkene) Ci Mechanism: «9 02:9 a i m 0 —~: -~ -— 3"” ace”? DA + L W- ° “(gm 0: (2) @ “29‘ Steps (in words): ' Stereochemistry: “WI; 0) a?“ W.) {a “have 4’ LEM Regioselectivity: MM 14141-3 *5 fi 3 "M‘l’buuL r‘flb Calla-M. ® “9" “M5 *9 WS" $ulo. CWV‘ (an-k) Other considerations: k @ mfmfimfih No dwoww Example Problems: ./ x / C] k Chiba F7 m l" Ci} i “2.0 “7 T ell irks—7 0*! it (on I 1 MI] W Addition of HX to Alkenes: - (I-IX + Alkene) Mechanism: G) (g) H M {l r» J $.79) m -—» 2» ——v —-7 VI Steps (in words):( 3 Stereochemistry: 9.0 “mic (HQ ‘. Hannah; Ail/4m t H NAE‘ % W‘D’Ti % C-C- {090194 Regioselectivity: Wdcouw'upd C) g vi? fugpemfi Other considerations: Mats possiyh Example Problems: {L fir L! (Em—am eh baa—fie Acid-Catalyzed Hydration of Alkenes: (H2504 + Alkene) Mechanism: ® ‘ \/\,C9 Q [m '1 H NH 4— RLS‘LH -———7 M —’2 % —7(:§\%/—7 0°“ ' @ “3'5: Steps (in words): Stereochemistry: {lam/ML}. CD 25mm 4 AKWC H ans to ieanrsutL) A @ Q‘s/7,70 (EHWASWH Regioselectivity: W‘Puwkod 6) HQ: Mu.) Cl. Other considerations: L355 W‘sewnt Example Problems: \ Who/(:11 0t Molmmsm /“<H \ 4.; is New 0/ 1’ H1304 m) V O<\ + “L904 7 \ 0H - z X “also;t —» CC C M (Kw 7 ...
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This note was uploaded on 10/26/2011 for the course CHEM 30A taught by Professor Chatterjee during the Spring '08 term at UCLA.

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Chapter 6 Week 7 Answers - Week 6 — Chapter 6 Chem 30A -...

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