F04 midterm3 key

F04 midterm3 key - Chemistry 30B Fall 2004 Third Hour Exam...

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Unformatted text preview: Chemistry 30B Fall 2004 Third Hour Exam December 3, 2004 M. E. Jung Name W Signature TA Name Hand in answers written only on this paper, using the reverse side if necessary. No exams will be graded that do not contain your signature! Read each question carefully before you answer it. Answer the easy questions first. Good luck! 2nd Hour Exam Chemistry 30B Page 2 M. E. Jung 1. (12 points, 3 points each) a) Name the following compounds by the IUPAC, Chem. Abstracts, or common nomenclature system, unambiguously specifying any stereochemistry. HOOCmCOOH ’3? flay «3’ flak—M e (~7Q/farmwwfl) b) Draw clear, unambiguous structural formulas (of the kind drawn above) for each of th two compounds. e following (Z)—3—Fluoropent—2-enamide P O WSW”; V1 Ethyl l-chlorocyclopropanecarboxylate CF Dbarowz aé 2nd Hour Exam Chemistry 30B Page 3 M. E. Jung 2. (12 points, 4 points each) Predict the major product(s) of each of the following reactions, showing stereochemistry whenever appropriate. If no reaction is expected, state N 0 Reaction. Assume a normal aqueous workup after each reaction. “9* Er 21) WI, 1)CHsCH2MgBr W W0 '4 “(a i :ég/Agf ___—_————> B” 2) mild H30+ '“> 0 o All. _.____..> b) a3» 0 1) MCPBA/A (\W n 2) aq. KOH/A “ 7% H ’CH3 1 : «1 W V’ W C) H O ‘7 a W 1)str2 1/ 2 C Ha , MW Q .. W5 2) mild H30+ 3. (8 points, 4 points each) Rank the following groups of compounds by acidity from 1 to 4, with 1 being the most acidic, 2 being the next most acidic, 3 the next, and 4 the least acidic compound of each group. a) ICH2CH2000H FCHZCOOH CH30HZCHQCOOH BrCHQCOOH s I 4 z b) CH30HZCH20H EtOOCCH2000Et CH3COOH CH3COCH3 ___3.__.E___J_.__‘I‘__ Chemistry 30B 2nd Hour Exam M. E. Jung Page 4 4. (16 points, 4 points each) Provide the reagents (or group of reagents) to carry out the following transformations. Note that more than one step may be required for each transformation. 0 CH3 0 CH3 HO CH3 A 6 5H CH 5 E 2 o/\OH O/\OH Chemistry 30B M. E. Jung 5. (10 points) Propose a detailed mechanism for this isomerization. 2nd Hour Exam Page 5 Chemistry 30B 2nd Hour Exam M. E. Jung Page 6 6. (12 points) Treatment of benzoic acid 1 with excess methanol and catalytic sulfuric acid (with removal of the water) affords a high yield of methyl benzoate 2. o 0 OH OH Ph/KOH ———3——>HZSO4 PhJKOCHS + H20 1 2 Write a detailed mechanism for the reaction, including all intermediates and resonances structures. You can use the shorthand notation that we have used in class (charges circled in one resonance structure and in parentheses to show where they would appear in other resonance structures). Also proton transfer between heteroatoms can be written as one step with the words ‘proton transfer’ over the arrow rather than showing the two steps, e. g., loss of a proton to solvent and then reprotonation of a different heteroatom in the subsequent step. .. 9 .. f) My»! H OS‘WM‘ I? aé Chemistry 30B M. E. Jung 7. IR: 2954, 2899, and 1724 cm]. 303014 1 2H J: 7.l Hz 2nd Hour Exam Page 7 (15 points) The molecule Best—TA gave the following spectroscopic data: infrared, mass spectrum and proton and carbon NMR. (/50 OO 0 intensity 73 105107 115 150152 3HJ=7.1 Hz 1H NMR 2HJ=6.8 Hz 2HJ=6.8 Hz 2HJ= 6.8 Hz Chemistry 30B 2nd Hour Exam M. E. Jung Page 8 7. (continued) (8) a) Show what structural information can be obtained from each piece of data. IR: C;Daj/?ZV gfs 04 ,t 4,71 4/ Md?) M+/m7‘-2/:?:l 7)% MW /§d/Is’2/;>&,Hufl;C€ mice MW MS: (7) b) Propose a reasonable structure for Best—TA. “QMZOflWé/Mfiééfl WB/maW Chemistry 30B 2nd Hour Exam Page 9 M. E. Jung 8. (15 points, as indicated) Transform each of the given starting materials into the desired products by a reasonable route, namely provide the reagents and conditions. (NOTE: More than one step may be necessary for each conversion.) You may use any other normal organic and inorganic reagents as needed. (4)21) 00 7O 3 l> NH; Méz/fim/ 3H30 Q. by agiéwz/ 2) W/a/g WW 3 a/D/IQ/LWSOLQW 8”? N” h/M 63 kiwi/54 H30 ...
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This test prep was uploaded on 04/05/2008 for the course CHEM 30B taught by Professor Rubin during the Fall '05 term at UCLA.

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F04 midterm3 key - Chemistry 30B Fall 2004 Third Hour Exam...

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