Practice Midterm 1 2010

Practice Midterm 1 2010 - Total Points 100 Please put your...

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Unformatted text preview: Total Points: 100 Please put your name on all 7 pages of the examination. Be certain that you have all 6 questions. Total number of pages including cover page: 7 Please Read All Questions Carefully Before Answering Them Question Points Score 1 18 2 18 3 16 4 10 5 18 6 20 Total NAM (1) (18 points) Provide the missing products for the following reactiofis.’ Br 31' °/\/ 6" a) (j + /\/OH NaH ? C or 0 NoH N V mm (61‘ 5‘" W W 31 9‘6 / NaOH b) st‘?’ ? O Oxph excess H! 9 C) /\ heat I CHsT- CH 5 (H‘ 1 O — [MM 0" 0H [i _ “NV? 1 ° ‘7»\ 3’3"" H \ disk“ 0 n I , Row \0 L \0 V d) E: excess Br2 ? 5' Wl/Kr L / Kr O N—Br a M“ i e) . m‘“ N 0 9 Br I)\/ 7/ {7' \M‘p I 3! 00:4, light sis-"L 2° Mb 44% (2) (18 points) NAME Using the arrow formalism, draw detailed, stepwise mechanisms for the following transformations. Show the major and minor missing compounds where required: (,1 HBr low temperature (MM “Km 1" mqu MWMAK mum“ ? v w \l M owwa 1 \ ‘V ‘ ' N l ' l H 51’ Sr” l.‘-l’ HBr ——> high temperature \ ‘mfih (,qu l’D MW wqw EA Fur 7&4me “whoa/mm llAWélAK —» mm ? SvlvshMcé aW-MM [Moth/ot— 141V H 9V? H J r \ ri E" l l JV L g] \ 3/ s “\w‘v“, “\Sk) WWW H US 3 ’ W” W3 M or V. a mu Moi or < ‘5 NW meq r $0 at) Ll wile \ NAME (3) (16 points) Show the structures and the stereochemistry of the Diels-Alder products: a) Q * Tozcmm ? m m 0,014, COICHS % O o \ I 4— “ 0 VA .‘xs 9‘ \/A 3‘ o Et02C c) + I ~———> ? 00, G \' a” H C02Et ' u °V / Mom 4 12:02}? H 3*“ co,» NAME__ (4) (10 points) Assume that all compounds shown are glanar. Use Hflckel’s rules to predict which one is aromatic, antiaromatic or nonaromatic. “\‘S W ‘- 4/ H“ Hail. Lt" no whnous wad-km f wmhu (s ) Csz k 5V3 \ ‘ I N/ (a l ‘9 l r l It t’ R u a MA «W‘Mflx‘c (a fit Z \ K N Mmech, mmh ( 0th mmn c NAME_ (5) (18 points) Draw all the resonance forms of the si ma com lexes for the sulfonation of chlorobenzene. Compare the reactlvi of chlorobenzene with that of benzene in this reaction and ex lain the regiochemistry of the electro hilic o w aWediated by halogen substituents. 0, Z slay/Mk cuwyums \ /—\' was“ Sulfunmhm :'c'\= a if}: "Cl" cl a “5% / l cl II + H \1 s - SU ’ “90“ 50 ‘ \'\o‘)\\° + SO? “3' / /5°s / 5 a (W .a, \ A,» 4——> 1 "‘ ’ W OY‘Ww \ / V V w L M“€€ECL C\ 'C\ cl \ C\ IT ‘ / WW mm fig _) \ \ H \ M 1 + a Wmstf V 503 \\/\ 30; “)H .. “\ cl 5‘ 3°)“ (N “sow q r Wm \ \ J‘ / / pgqb+allgfifl \ \/> 1' / \{k V \KK‘ Slow achwm \ 2 Avg; \M’Mflu (M h 6 Wad) kw use/mm; éwh Hannah/ms m M V‘Wj ’“j “'3‘ M by m mm lel‘m \‘W\ W. Tlm‘s Nam/lama domh‘m B an M MW 0‘“ Pam swsh‘hhw _ Compavwl t6 mum, or’ma wé yum SWsh’thw‘ [14 MW how M um moan 5%, if ‘\L\7W’“WVN slrmw MKUlen ML Hams/w, as My m dwellme . cmowuuwu rs sh“ VLSS th, Mm Wm WMLMWSS, M h? "Wr’ Mlewn um. swsh‘wnwx 4‘qu OHM» MW W 1 PosWflMS, ' (HMOWS’ almanwhmj ‘ oleo-patm :3me) Wed}. 4/ $0 NAMEJéfigR¥ (6) (20 points) Draw the molecular orbitals of butadiene and conclude if you can obtain a thermally allowed [4+2] cyc oadduct from two molecules of butadiene. Show the structure of the product. fl N ‘l n c, b ‘ v A i x: gnarl”) = 11' «meg ,_——— LUMD Air wit” LT MAW? ‘MIMUWLL Kl “ll 2 9 fi l we: lo HWW MA WMO AN symmlm’ AUW‘LA J ...
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Practice Midterm 1 2010 - Total Points 100 Please put your...

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