HE1Key - Initials k E-Y CHEMISTRY 152.002 Spring 2005...

Info icon This preview shows pages 1–7. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
Image of page 7
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Initials k E-Y CHEMISTRY 152.002 Spring, 2005 February 8, 2005 HQDR EXAMINATI! 2N I i n in r I 35 II 45 III 35 IV 15 V 20 TOTAL 150 Exam Begins Here I. (35 points). In the answer area below, darken the space of the most appropriate response to each of the following multiple choice questions. ANSWERS TO QUESTION I a ‘ b V c d e a b c d e 1. f/ l l/ // H 5 l/ I // l/ l/ 2. If I l/ U fl 6. l/ f/ I l/ l/ 3. If fl I [I H 7. If If U I H 4. If H I H [I Initials kE X 1. Assuming that each of the following structures is planar, which would most likely NOT be aromatic? EN» “32”“ (ET/Q D A B C 2. Which of the following dienes would be least likely to undergo a DielswAlder reaction with maleic anhydride? C) ’W C: CH3 A B c D E Br Br Br GA A B C a. A<B<C b. B<C<A @ A<C<B d. C<A<B e. B<A<C 4. Given that the trifluoromethyl group is more electronegative than chlorine, one would expect trifluromethylbenzene (C6H5CF3) to react with BrszeBr3: a. less rapidly than benzene and at the 0/1) positions. b. more rapidly than benzene and at the o/p positions. less rapidly than benzene and at the In position. (1. more rapidly than benzene and at the 11) position. e. one first needs to know whether or not there are electron pairs on the CF3 carbon. Initials K E— I 5. The following acid—base equilibrium would: OH O' 0‘ OH + CL —~— + CL CH3 CH3 N02 N02 a. lie to the left. (:9 lie to the right. c. neither (KBq = 1). d. not be determinable without knowing the equilibrium constants. c. depend on the particular individual doing the experiment. 6. What pair of starting materials could have been used to prepare the following Diels-Alder adduct? CH3 /CH3H CH3 CH3 m + if” 353301 Cm“ 1002 (GEE: H30 / CO2H 002H 3 3 %r—J \ _. .______J K _/ p___ ,__J A B c D a. A b. B @C d. D e. That compound 13 not a Diels— Alder adduct. 7. Which of the hydrogen atoms in the following molecule would have the smallest bond dissociation energy? (3) CH3 A ( )HchfJ—l-ll (D) CH3 (0) and D would have essentially the same values. Initials E E E II. (45 points). 1. Using concepts developed in this course, propose a mechanism, using curved arrows, for the reaction of l—chloroanthroquinone A with methoxide anion to give 1-methoxyanthroquinone B. What mechanistic type is this reaction? Acléfi'km - Eliwm ' 0 CW 0_ 00H3 9mm BCH ’ GD 3 +04 O O A B ‘l ‘1’ 0 at 0043 Ocj) Coopers \ :1 H ©69\ 0 O (C6363; moon—Vorm) 2. Would you expect the compound shown below to be aromatic? Explain, making specific reference to the criteria required for aromaticity. . '2. ' ' . 9H3 B is S? W 5“. eA) _ B has 0—. ”P orb L - \. Cydtt ‘ / \ ' \m ”e a? -— . a.“ m 2 on“ . 81PM” 0‘5“ A. b“ 8‘5 (An-Fl) “2%- 1/35,) t+U~> Magnum. 3. One of the two allylic chlorides shown below undergoes solvolysis significantly faster than the other? Which one and why? M $13 or 6-: ® «CZ/k M g 3 HacBCHs doubly octlylic /;,1° Coxloo g . smgmmjs: /\ \ e; mas-a a. gags M Q9 -' Qfii‘m— $“k610\e' CG) £WA (e. more S'l'mlo‘e. W e. \‘R “1'5“ 4A4. Cg) m i- .'. LS?— ‘5 @Mx ’Ab§_>1\\ 5 SO\U0\\/%°‘ were. twp—Ely. ®_ Initials kE—T III. (35 points). Draw the structure of the major organic product of each of the following reactions. Indicate stereochemistry if it is an issue. H30 Q02 “ 1. Na20r207/H2804IH20fheat Q3 CH3 CA or NBS/CClfl/hv \ 2. me (3: / c| MeS'(1 equivalent)lMeOH Ck MS _ U53 3- \/\I/\/ _ . cw \/ Br 1 2J,cant Pd(PPh3)4 (cat) ET 3 | + __.___., H MeCN/EtaN ' H30 . 1250011 8 h U43 4 OCH3 note: During the reaction Pd is O bonded to carbon 2. W (3% \M‘K‘AWM. Iniaalsme IV. (15 points). A bottle labeled “nitrobenzylbromide” did not specify which isomer was present. The 1H NMR spectrum of the sample is summarized as follows. 6 4.55 (singlet, 2 H’s), 6 7.52 (triplet, J = 8 Hz, 1 H), 6 7.75 (doublet, J = 8 Hz, 1 H), 6 8.17 (doublet, J = 8 Hz, 1 H), 6 8.28 (singlet, 1H). The proton decoupled 13C spectrum had peaks at 6 31.1, 123.3 1238,1298 135.0, 139.7, and 148.3. From this data which isomer of nitrobenzylbromide was present in the bottle? CHaBr CHZBr CHeBr C“ E: No2 gaze am an 5 '1-52 0.0 “a“ was . t . w +6142. H H MR 0‘ Note: 1H NMR chemical shift values for ArH are generally in the 6 ~7 —- 8 range; ArCH protons, 6 ~25 — 3.0; CHBr, 6 ~28 — 3.1. 13C chemical shift values for aryl Cs, 6 ~110—160; C—Br, 6 ~10 — 25, Ar-C, 6 ~ 15—30. Initials t E I V. (20 points). Show how you would prepare the trisubstituted benzene compound shown below from benzene and any other reagent you might need. Show the structures of all isolated intermediate substances. Reaction mechanisms are not necessary. COZH © " B' W No2 «v Q63 &\ 3 M: ”01 0&le \ 3 fight 01 / lxcH- @an QM3. HNO3/“25Qk C\\:3 (+8 \Me ergo/met; i _____,> \ -; cart :3} —————3> NO; but} Q02“ Bf fiat Cr Cb"! (Blake 3 : 9n- Hle ’11 l \ ‘~ Br N01 ‘52.. _...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern