Chem 308C_Summer 2011_Exam II Key

Chem 308C_Summer 2011_Exam II Key - Chemistry 308 C1/C2...

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Unformatted text preview: Chemistry 308 C1/C2 Exam 2 June 27, 2011 _ \ Student Name (PRINT CLEARLY): C / Student Signature: Section Number (C1 before lecture, C2 after lecture): SEAT NUMBER: Instructions Please fill out @ of the information requested at the top of this sheet. USe a pen for this, not a pencil. This exam consists of 12 multiple-choice questions and 8 questions requiring written responses. To answer a multiple-choice question, circle the letter cormspgnding to your answer. Questions requiring a written response should be answered clearly and leginy and only in the space provided. Please answer all questions within this exam booklet only. At the end of the exam, you must hand in this complete exam booklet. Do not separate any of the sheets in this booklet or remove the stapl_e. Do not hand answers in on extra sheets. The length of the exam, including time allowed to fill in all responses. is 70 min. Exam Form Number. 1 Draw the structure of the compound with molecular formula C IOHIZOZ that gave the 1R, 13C-NMIR \ . and 1H—NMR spectra shown on the handout page for this exam (3 points)? 0 Hr or 28“” www- /§)\Q /\/ LQ‘T‘, v \“x b 3‘ 0 g Q 5 0 r a.” \\/\ “J ’2. Draw the structure of the major organic product expected from the sequence of reactlons below (3 points) 0 0 . . 1. SOC] , nch e,A 2. Benzene,AlCl3 3. dilute aqueous acid mechanism for the transformation shown below. Use curved arrows to 7; . Write a detailed reaction ements, and show all formal charges clearly (3 points). indicate all electron mov fl. 0 O .0 CI/CH3 NaOH, H20, A 09 Q ’ e {9.13 (4— Hum) 1 fl .. (-3 O :o: h 9 (é ('I—O'I/ 3 \---* [IR] \0 H "l Q‘s“? V w v (or on Total points this page (max 9) = 4’ . Which is the correct IUPAC name for the compound shown below? sir—cl: your answer (2 points)? 0 A/U\N J\ H A 3—amino-2-methyl-4—heptanone E B l N-(l—niethylethyl)-butanamide C dimethylaminobutanone D 1-(methylethyl)arninobutanoate E N—(isopropyl)butanoic amide S . Which is the correct sequence of reagents and conditions for the synthetic transformation below (2 points)- 0 ‘? __________——+ OH Ugh! I HNO3,H2804 II Br2,Fe III Mg0,THF IV (i) 00;; (ii) dilute HCl AI,H,IH,1'V B II,IH,IV,I (C)II,I,III,IV D II, 111,1,IV E I,H1,IV,II 6 . Which compound will react most rapidly with methylamine (CI-I3NH2) in pyridine to produce an amide in good yield? flfl‘ le your answer (2 points). 0 O O 0 OCH3 H H II OCH \\. / /c\ 0 s o c C 0 CH3 0/ \CH3 Gama OCHS , com 0/ \CH3 NO2 A B C D l E :1: .No2 Total points this page (max fl) = :} . Show how you would perform the synthetic nansforrnation below in good yield. More than one reaction is required. Number the reagents and conditions for each reaction separately (3 points). \, Lot—L ’91 (“$31 '3‘ Riga? (of gauge) 0 O 7,. Nam-wag A (3990 l _ Cg, . Draw the structure of the major organic product expected from the reaction below (3 points)- 0 H N )|\ , NaB(CH3C02)3H, Y i 7 9 CH3C02H _ ' /N\ Total points this page (max 9) = ‘0 . Which step in the reaction mechanism shown below is the rate determining step at pH greater than 8‘? circle your answer (2 points)? 0 A 09 B OH C OH i + (Iii-I3NH2 # + __——--_ —l—— :2- + H%\ H2N \ HN \ Ct) Y Y (Jam-12 \ F @\ E HN\ \\ . Rank the compounds shown below according to their reactivities with sodium methoxide in methanol (> means greater reactivity than). gale your answer (2 points). K Cl L M Cl N F\. : : Br E J O : : \ \ N 2 N02 CH3 AL>K>M>N BN>K>L>M CM>K>L>N DM>K>N>L EE)L>M>K>N F N>K>M>L ‘1 . Which compound(s) isfare 14mm in dilute aqueous acid? Qirgle your answer (2 points). OH \N/ 0 >< I x H m/u\ W O O o 0/ k) A IandIV 131,111de iC)I,II,DIand1'V D Elonly E. LII,de F II andIV Total points this page (max q) = .n \ 5 . Write the IUPAC name of the compound shown below (3 points)- M /\ 62%;} IZ‘OXO‘D‘iXWPQQ‘kQ 0 (on W (0 m ‘1? . Show how you would use a thioacctal for the synthetic transformatiOn shown below. More than one reaction is needed. Number the reagents and conditions for each reaction separately (3 points)? \' “3M” 0‘ H's/VS“ ). Cakafi-LSM (etc-31,03. O ? q, , a»: Ll. (/WLD \HLH 3' Mx (Xiwfi’c :13 4—. “Seczri¥iq’(3°+,H—LO 1® (“a 0Q 0d“”%fi1 HCI HO A 0 U! 2 /U\ n/ ~ 0“ T at w w \\ mm ’W (kW 6“ M“ 9%?“ g ,‘ n \ V" E" '\\‘. H on w 0% 0“ 5 K5 H +N/ “(73 T; HE r)" H ‘ ‘ r 0H ' g-o OH ‘ H Total points this page (max 9) = i6 . What isIaIe the major organic product(s) expected from the reaction shown below? Circle your answer (2 points). CH3 NaNHz, NH3, —33 °C _______————-h- ‘2 CI I CH3 H CH3 1]] CH3 IV CH 3 H2N H N 2 H2N Cl CI NH2 A I only B I and II C II only D Iflonly E [[1de F IVonly i?” . Which one set of reagents and conditions is expected to give the best yield in the synthetic transformation below? Qfl' In your answer (2 points). 0 OH '? CH3 CH3 A HZNNH2,KOH,H20,A EB)NaBH4,CI-I3OH c H2,Pd-C D KMnO4,KOH,H20,A E Zn(Hg),HCl,A Total points this page (max 4) = l 63 . Write the names of the functional group in each molecule below (2 points). / o N gOH . ll“ ‘ . , _ Q “KXW\ PDQ kWu‘u M ‘23» fl . Cyanohydrin formation by the reaction of carbonyl compounds with KCN and HCl is an equilibrium reaction giving a wide range of yields. Rank the compounds below according to the yields of the cyanohydrin product that you would expect to obtain from them in this reaction (1 = highest yield of cyanohydrin, 4 = lowest yield (2 points). NAME: N0 O 0 0 0 cm? \AH \JK “\Jx. W '1 Z l 4- 10. Write the reagents and conditions needed to perform the synthetic transformation below in good yield. w all ' term ' c ac ' Note that the use of a protecting group is required. Number the reagents and conditions for each reaction separately (3 points). five“ GAL “(Ref 3611804 RANK(1-4): O l; H0 ) 0 OH ‘ )k/Br 12. MBITHF M ' o‘A ' 9 mn/ L 3. /i\\ /\ AA“): sttq o. .. - - ear 8’ JH’LQ‘l __ fl 0/ A 0/ 0 GE) Total points this page (max 7) = ...
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This note was uploaded on 01/12/2012 for the course CHEM 2347621 taught by Professor Mr.boikes during the Summer '09 term at Rutgers.

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Chem 308C_Summer 2011_Exam II Key - Chemistry 308 C1/C2...

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