FraenkelMT1Key

FraenkelMT1Key - 00206 1. Steps in mechanisms. Complete the...

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Unformatted text preview: 00206 1. Steps in mechanisms. Complete the steps only. BALANCE. (3 pt. ea.) d)”, .. CH d ‘ H’gr'i 3 (a) 11.3;- + ©< 3 fastest \ + u H \/ I M H 3 (d) £9 + {ojHe—————_> O S tereochemistry.’ :9- H H H U © 3 (e) + H®___+ 7/ L“ a H H H/X H H H H H 9 CT); 0 3 (f) NH3oe + (CH3)3C—-CEC—C(CH3)3—_»@H3\3C-Czc—-C(Ci“3\3 W3 CH3 HSC H " \I 3 (g) NH3 + __c\@ ———————» >_—_—< + : HZ H CH3 H CH3 (—3 O N\ .. " \ .. 9‘ 3) (h) NBr + 1193.339 _______, —(' Bra 0 M Page 1 total a; 3 (i)(CH_~,)3C-H + {C2}. / \ H ' ‘0: 9 OH 20: ”\ ll . n l ., .. " Czé' :Cr —”H 3 0) H302 + H—$—.Q—fir—_QH_, H30® \\ H ?x C113 OH :0: “$3 - =0” ‘ I .. n .. we) ’\ , n 9 3 (k) H30. + H—C—O—Cr—QH H30 6:0' _ n I " n “ ’0‘?“ OO. mm :0: \ 2. Complete the following reacitons. (2 pt. ea.) M— fOo REACTcoM Z (3) Br: + Q C¢E5c~ \\ 2m + 0W 0%, o( O’lQ 0‘ ’Hl-o‘ Z (c) 2K + (29:05:an Sl‘fiJC/‘l‘Ul‘Ql \MW M N“ H Na® ,aHe “03 H 2 w) H Q Hzo: H O ZHH (a Page 2 total l ? 00206 H2 1 t ethaaggal N Z 05 + Na®+ 804'2 (f) : z, : : , + \$ / 4+ 001303 HOCHZCHZOH S \ _. / 3o= H20 a —\ u ' — H H CL 8 (g) g + 5535 ’ A 813006 H H H/ H N» f CH3 Ramaaa 9th!ch (h . ,_ Z ) CH3 H L149 /® +K9+H2 D Z (i) excess l‘lz, PIOZ, 10 atm -———————-———> 60 OC. ethanoic acid CHgCHQ CHZCH3 Z (i) H “2 >=< C HC ‘rrzz— CH C Lindlar's catalyst 3 1 Z H 3 / /M/CC“‘“*\\\ H I I /' “(ll/ \ C] C] Z002 Cl C] CL C] (Diels Alder) CL I d C L Page 3 total L CH3 CH3 H 2 (I) + —*____> :0: :0 “\0/520 //oo 3.0. CH3 ‘—‘_” CH3 cu} @ng g — c: C c HQZ CH3 1), 2N§DSO§2 ‘ 2 (m) O\O/ quz HQ: ‘(3H 39. ( 504,1‘> (Don’t balance) 3. Naming. (1 pt. 6a,) CH3 q vb {— gene (6) “) N "as U (A ‘ Ambew K” \Jfl Cl C I fimflw fl ‘ (b) (0 O3 0204 Q \x Cl ‘ m. w. WW“ . \ / 9"qu " +fch0ro+O(UQ/\'Q / CH (312/ 3 ~—~—\ MM M , (I), :3) ost n O ‘ . \ I (c) [>9 on FM Q (s) . //‘?§§p.: 931% r (generic) (generic) i) , OSMK UM r0569? (d) RCOOH PU 0K3 K) (h) 0504 (generic) Page 4 total J]; 00206 4. Electronic Structure. é (21) Draw out the electronic structure ofbenzcne, 3D. (6 pt.) Ti —» G A" b“ “3‘0 '9‘)" H H 6’ > “fktl HOT 31): w M W Cor-ll— taut )<::: lph gr 0— label 4(' (b) Show how alkyl groups stabilize free radicals by completing the diagram below. (4 pt.) 'TA MOTE 2 X . W l QLM T omlap‘) 002409 balm efin P 00,,” C . Orlzn‘l'ul b3: §P3 Orh‘h' OA\3 MPPMS OVA boflx orLi’rols m m m Tr saw; Marat , Q (C) Draw three resonance structures of the pentadienyl cation (C5H7+) by completing these diagrams. (2 pt. ea) ‘l ’l l l" H H H C C / H C C \C¢ \C¢ \CGD \C¢ \68/ \\C/ l I \ / I \ H. H H H H H l H \C/ \C/ \\C / I \ H H H Page 5 total (d) Cyclobutadiene dianion Structure A Delocalized (?) Localized H H H /H \l T/ \Tthle CQC Ghee / \ / \ H H H H n Energles TE Energies 0‘ T257 “ a 4‘7 4L— each 0 oz o+ZB ‘1{* each C=C 2a+2B (1) How many I: electrons? Try 6. 6 Z (2) Populate the It elctrons into the It energy levels for the delocalized structure (A) above. (2 pt.) 2 (3) Add up n: for structure A. (2 pt.) [fixatx ’5 4K _ + Zx (M255 2 +2u +93 — 60H 4F 2 (4) Add up 2B“: for structure B. (2 pt.) 4X (1)0 Jr ZN +15 Ii €9<+Zfi Z (5) Circle which is lower: \. Page 6 total 8 00206 (d) What is aromatic. anti-aromatic, and just n0n~ar0matic? Fill in the table. (1 pt. ea.) Page 7 total 6 5. Road map. Given the clues, determine the structures ofcompounds A through E. (3 pt. ea.) WRITE YOUR ANWERS ON THE NEXT PAGE “ Page 9 total _ < @— Page 9 total ...
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This note was uploaded on 05/18/2008 for the course CHEM 252 taught by Professor Fraenkel during the Winter '08 term at Ohio State.

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FraenkelMT1Key - 00206 1. Steps in mechanisms. Complete the...

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