322B_2ND_PRAC_ANSWERS

322B_2ND_PRAC_ANSWERS - 322b Practice Second Progress Test...

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Unformatted text preview: 322b Practice Second Progress Test Spring 2008, Chapters 15—17 1. Rank in order of decreasing stability : + + GHQ+ CH300H=CH2 CH2 CH3 H s r? e a C m,» ykzfi Q> éJJW . . 5%?acw 2. Circle and name the functional groups. OH O o , CH30HO ,’ C)< 3 ' 0 j I C??? 'W #fiEw/aé 9amcz NOH , Q—cI—ICN , OH axiom o , O=NCH3 a: em" 6,2 mam 3. Write acceptable structures of: A a) 2—methyl—3upentanone a, Wig”, o b) 3-butenal 0) 3-methyl-2,4—pentane dione - LR d) acetone {3.3 {5 Ms E , e} 4-penten—2—one - . Write the resonance structures of + a , .,_ . $+HBT H 1* fil’c‘r" QC“; g Q4“? H5 it Hos w C>= + e a. b. c. d. [CH CO] 4.. Elfin; 3‘ ” 0/ “2 it '3 CrrgC I?” OH , _ . _ “ gm 5. (10) Give the structure of the dominant tautomer in each case: 0 o o OH 4 OH «- O “0* 0r :3 0 it 11 or 11 it it / 0 x. \ 0 Li 0‘1] I» “ é ‘/ / 1 / C7 / a 6. Write the mechanisms including all intermediates, formal charges, curved arrows: H_ a. 0mm is. Q— HCN c. U 4— CN U H511—1m0~__acm“w 0%”...0”: / OH Ofli—LHCM b CH U - / 3 /CH3 Demo? Ph3P=C -———+ ©—crr=c + (Ph)3PO ‘1 \CH \CH (Ciro/3325'” PM; \ <73 .539 —/ 3 -‘-= , ihPro CCU; H+ C Occrw CHQiJ —+ QCH=CH—CO—© 0 fl * ,9 , / {QH’H CF + H20 ,4. {‘4 “NC, '1 ,___._, PEN _/ ‘2 FA fig- CHZ—CIL, P1,, (3 69;,“ It: k5; 5:3” + 0L4 “V’me ~+ thcfi, EC, 0; H+ 0 0 “+044 d. \3 CH3OH4~ T OCH3 . - 'x" x “it <5”, w“ «a ---+ C53 “fl”? 7. Write the structures of the predominant product. "if 3 H+ OCH} a QCH-o + 20H OH ___» O CH", - - 3 \OCfifi OH'Ih t -— b_ CHO ea \ cu... 0 CH=O + 6 00 + HZNNHCONHZ —-——> '3’: “I!” M“ C0 “’99 RL' ' / (£3 d‘ PhsP + CH3CHBrCH3———>- ——-—'> Plus R": C sac-H3 o Heb“ _ H 0 e- O —"'—"""‘",’ 5 0 + 0 > aqueous (d. > HOW- . IBAL- H 9. gm L: 0 “cud o 2. H20 ~— OH_ \ \ * 1 heat / h. Br AtCI anH . . i. CH3COCI + Q __3» fig...» c313 glam J; + HNOH ' C‘.:N(‘)i¥ j. Qflfj _fi...2 H 0 H30" “30+ :2” u CCgJ— 5. k- O—MgBr +(CH3)ZCHCN—-> > “9 5-2. HO ._. _ Cg; I. CHscficNa +CHSCOCH3w——>—-—2—> Olga-SC 2% ‘5’)?» m. a ‘ Ii _ O—CH=PPh3 +CF|3—-G~CH3 “eat _, @CH: C(Cflsjz II 0 n. _ ‘ <;>-CH=CH2 + Cone. HBr —-———> H CH5 ‘" m 2 + 02 m, __-———-——> ‘3. heat D' V _ .. H3 + Conc. HBr Ego—FL)- O qH C- H2 37’ || C“ #3 CH2 8a. Synthesize CH3CH20H =(130H20H starting with alcohols of 3 carbons CH3 or iess as the only carbon source and any other needed reagent. OH FCC . /\/ _———-‘pr/\CH:O . “:0 fig 23 a 3—2 A My” 0 u I ‘9‘“?— Cf MCHZO ._____'»F- meK/“CTL .dgtaw’r b" I CH O Synthesize z i3 8 using any acyclic starting product I 3 + 0 iii if ‘5 CH3 ' K ‘3’ . "" 5 A g... and any other needed reagent. 1 M .L on" O“ c. Synthesize OKCHa from any suitable reagents using the Wittig reaction. Q .1 0:0 4 Fig I, g C? ...
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This note was uploaded on 04/25/2008 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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322B_2ND_PRAC_ANSWERS - 322b Practice Second Progress Test...

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