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Key_Exam_1_SUM_08 - Name(Print<€ T.A PID Section(see...

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Unformatted text preview: Name (Print): /<€ T.A.: PID #: Section (see below): EX.A_M_1 CEM 252 — Summer 2008 July 21, 2008 - Dr. Ardeshir Azadnia (White Version) 133.6. P0'_mts m 1 8 2 8 3 10 4 9 5 9 6 10 7&8 24 9,10,l l 22 Total = 100 points Exam Score Recitation Instrucq Sc_lus: fa 7 7 -_ , _ .—— Da Tme i— —Room_ Aman Kuls estha M 8: W, 11:30 - 12:20 Dmytro Berbasov Tues 6: Thurs. 9:10 —- 10:00 206 : — : ' 1 Nilanlana Majumdar M 8: W 10 20 11 10 — 36 83 204 183 —_—- l. (8 Points, 2 points each box) Give the correct name for the following compounds. NO2 a) 5 1,. fl 1 , NO2 NH2 g 0 13) (da 2. ‘I' 5 o c) (a 1* SH 2/4—dinijtroanK \‘mt. «or l—avm‘no— 2,4— 0' 'In'rLfo benzene 4—- mercaP+ow 2—bu+-=Lnona 2,—aLalime-tfiylox i (an e Q-MQ‘Kyl—lw Pro/fine. oxu'oL—Q ,2— meTfial-bl- epoxyffa Pang ”4‘. “2" 2. (8 Points, 2 points each box) Draw the correct structures of the following compounds. 3) Isobutyl propy! ether >/\ O N c) 3—Cycloheptenone c) 4-Isopropyl-2-dodecanol d) Benzyl alcohol " WA" .5}. 3. (4 Points, 1 point each) Mark each of the following compounds as aromatic (A) or not aromatic (NA). HN I H at” a an 4. (6 Points, 2 points each) For the following pairs of ions, indicate whether one is more stable than the other or write the word “Equal” if you believe they are of equal stability. + c: C' I 11 SH SH 6 No2 @ mo2 I II CH26H3 CHZCH3 e : Br I II 5. (6 points) Show the mechanism for the formation of the following reaction and give the structure of the final product in the box. 6. (3 Points, 1 points each) Give an example of each of the following in the appropriate boxes provided: A hemiacetal Hydrate of actaldehyde An acetal 7. (9 Points) Propose the structure for Compound A (CHI-1140,) that has the following lHNMR spectrum. Hint: Upon reaction of Compound A with 2,4~dinitrophenylhydrazine, an orange solid was obtained. Compound A does not react with Tollens’ reagent. lHNMR 6 7.7, doublet, 2 H I" 6 2.2, singlet, 3 H 6 1.7, sextet, 2 H :\ x a 1.1, triplet, 3 H \:3 8. (10 Points, 2 point each box) Complete the following chemical transformations. 331/123 % % 9'3 a) 3) PhMgBr Ho P 1" 4) H30" i‘ \ c ”3 o 2) ph3p=CHCH2Ph b) 9. (6 Points, 2 points each) Complete the following Williamson ether synthesis. H0 @390 ”a NaH an alcohol an alkoxide ion OCHQCHa /\ E, f 10. (18 Points, 6 Points each) Outline an efficient synthesis for each of the following compounds starting with the given starting material and any suitable reagents. Br CHZOH \) cugscge“) —0H. .12) 5(2) [2&1513 Br 6r 6i” 5/ 11. (22 Points, 2 points each box) Complete the following chemical reactions by filling the boxes with. reagents, reactants, or products. For products, only give the major organic ones. OH 1) 1313.:3 2) NaNHz E a) 3) PhCO3H 4) (CH3)2CHCH2CH2MgBr OH {40,6 0 1+ 2) AgZO. NH¢OH 1) (CH3)2CHC1 @L ——-—-———h— ‘9 AICI3 o H . I 2) KMnO4, H20, heat 3) 1mm4 4) 1130* In O 00H3 g) l) DIBAH 2) H20 1+0 CA} N ...
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