EXAM 2 COLAPRET - LASTNAME: HRSTNAME: | AHMAD COVERPAGE...

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Unformatted text preview: LASTNAME: HRSTNAME: | AHMAD COVERPAGE Instructions This exam will be closed book. No notes, books, calculators, or molecular models will be allowed. The exam will be comprised of two distinct parts: ' H 3 O EXAM Part I will consist of a series of multiple choice q . questions. Your answers to these questions must be a t A. submitted on a Scantron “bubble” sheet. The answer sheet will be provided for you, but you will need your own #2 pencil(s). Only answers marked on the bubble sheet will be graded. Answers to Part I questions marked on the exam itself cannot not be graded. No re-grades will be possible on Part I of the exam. Part 11 consists of questions for which you will need to write out your answers, using structures and/or words. This part of the exam will be hand-graded. Answers for the Part 11 questions that are written in pencil will not be eligible for re-grades. Answers written in pencil with ink overlay will not be eligible for re-grades. If you use a pen to answer the Part 11 questions, only blue or black ink is acceptable. Answers written in red ink cannot be graded. 1. You must have your valid UT ID card (or other govemment—issued ID) with you. You will need to show it to the proctors when you turn in your exam. 2. Chapter 4 of the University’s “General Information” catalog outlines this university’s policies regarding exams, as well as other quizzes administered during the semester. Specifically, students are expected to remain in the exam room until a test is completed. These policies will be strictly enforced, with no exceptions. You may not leave the room for any reason until you are ready to turn in your exam. If you wish to leave the room, you will need to turn in your exam to the proctors, and you will not be allowed to return. Please, plan accordingly by using the rest room before the exam starts. UTID: 10/20/2008 CH310N-Exam II Ver. A Objective Test Section Identifil the choice that best completes the statement or answers the question. There is only one correct answer; please carefully bubble your choice on the scantron sheet. (3pts. ea; 75 pts this section) Ml“. What is the major organic product obtained from the following reaction? 1 OH O O 2 H2NNH2 KOH —> 4 & triethylene glycol A 3 NHNH2 {loo-‘20 43me 2. What is the best choice of reagent(s) to perform the following transformation? 0 ? _> OH OH OH ,/ V o O a. 1. LiAlH4; 2. H3O+ b. H2, Pt 1. NaBH4; 2. H20 (1. NaH V5. What is the correct assignment of the names of the following functional groups? C Hy H3 i m C H334 1 2 3 4 a. 1 = acetal; 2 = hydrate; 3 = acetal; 4 = hemiacetal by 1 = acetal; 2 = enol; 3 = hydrate; 4 = hemiacetal c 1 = hydrate; 2 = hemiacetal; 3 = acetal; 4 = enol d l = enol; 2 = hydrate; 3 = hemiacetal; 4 = enol V4. What is the major organic product obtained from the following reaction? 1. Ph Li 0 EtZO \JK 2. HSO+ I M, ’ a. 2-phenyl-2-butanol " b. 3-phenyl-2-butanol ,4 l c. 3—phenylbutanone g d. propiophenone,PhCOCH2CH3 - 5. What is the major organic product obtained from the following reaction? 0 O \ANHZ 1 2 1. NaOH, H20 ——‘> \i 3 OH NHCH3 2 H3O+ 9-79.69 hMNH 6. What is the major organic product obtained from the following reaction? \/ O 0 OH OH 1. 2 eq. CH3MQCI OCH3 ——> 2. H30+ OCH3 1 2 3 4 a. 1 b. 2 3 d. 4 7. What is the major organic product obtained from the following reaction? 0 O &H \JKOH 1 2 O HOAACI V\OH 3 4 .920 AbaNr—t 8. What is the major organic product obtained from the following reaction? HO O 0 H20 OH —-—> 1 2 CI 0 O H OH 3 4 goers» AMNH 9. What is the major organic product obtained from the following sequence of reactions? 0 O O O i H CH CH / 3 3 3 /"’ 11. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound? OH /V+\/ :> CH3Br CH3CH2CHzBr CHacHzBr (CH3)2CHBr AJOK/ \/(fi\ \(i\ 0 xi 3 4 c L, La. only 1 and 2 b. only 3 and 4 c. only 2 and 3 d. only 1, 2 and 3 12. What is the major organic product obtained from the following reaction? 0 OH \/\N/ W \ANX \/\N/i\ H H 2 NH2 3 4 1 a 1 ML’W “4qu b 2 I 6’ 3 :02 d 4 \° C/ l H 13. What is the major organic product obtained from the following reaction? 0 H2. Ni \ high pressure 0H a. 2-pentanone NR b. (E)-3—penten-2-ol e; 2-pentanol d. 4-hydroxy-2-pentanone /l4. What is the major organic product obtained from the following reaction? 0 o O O A A A i Ph NH2 Ph NHCHZCH3 Ph 0 Ph 1 2 CH3CH2NH2 ———> O i i Ph)i\ocH2<:H3 P“ T 3 4 (:Hch3 a. 1 2 c. 3 d. 4 15. What is the IUPAC name of the following compound? & a. 4-phenyl-3-hexanone b. 3-phenyl-4-hexanone c. 1 ,2—diethyl-2—phenylethanal d. 1 -methyl- 1 -phenyl-2-butanone 16. What is the major organic product obtained from the following reaction? 1 2 OCH3 1. LiA|H4 —> O 2. H3O+ 3 H 4 O/\OH a. 1 / \\. /\ .. r r y! £5 3 U /l d. 4 “x w“ )/7. What is the major organic product obtained from the following reaction? 1. PPh3 A 2. BuLi "n./ ‘v\ 3. CH3COCH3 “75’ 9 '5 4. H20 \/ \/\ ——————> Br ’ , H a. (E)-3-methyl-2-pentene C H37 \ p/ M i b. (Z)-3-methy1—2-pentene C 2-methy1-2-pentene H l d. 4-methyl-1-pentene (I. )8. What is the approximate pKa value of acetic acid a. —2 Lb. 5 c. 15 i d. 35 19. What is the major organic product obtained from the following reaction? 0 CI OH Cl 0 $0012 1 2 ——> OH O 0 3 4 20. What is the major organic product obtained from the following reaction? / o o o 1. (CH3)2CuLi Cl OH H 3 4 2. H20 1 9.0835» £DJNh—l /21. What is the correct assignment of the names of the following ketones? o O O 1 2 3 a 1 = acetone; 2 = phenol; 3 = benzaldehyde (9. 1 = acetone; 2 = acetophenone; 3 = benzophenone c 1 = formaldehyde; 2 = benzaldehyde; 3 = acetophenone d 1 = acetaldehyde; 2 = acetophenone; 3 = benzaldehyde 22. /Which of the following compounds is a 3° amide? / 1 o 2 o 3 o 4 o 13th N(CH2CH3)2 PhiNH-tBu PhiNH-Pr Ph)J\NH2 (a; 1 b. 2 c. 3 d, 4 23. What is the major organic product obtained from the following reaction? HO OH _. /Q\ Phi O 1.HC=CLI Ph 1 k 2 k / Mk 2. H30“ Ph 0 —> Ph H M Ph/\/\ H 3 k % 4 1 b. 2 c. 3 d. 4 / 24. What is the major organic product obtained from the following reaction? COOH CH20H Br OH CH0 1. Mg 2. 002 3. H30+ ——> 1 2 3 4 9.03.335» AuNi—K 25. What is the major organic product obtained from the following reaction? 1. CH30H2CH(CH3)MgBr O 590 M 2. H30+ H 2,3-dimethy1-3-heptanol 2,4—dimethy1-4-heptanol 2,5-dimethyl-4—heptanol 2,5-dimethyl-3-heptanol ©®¢P 10 CH 310 N EXAM #2 UTEID PART 2: Free Style Answer Format (75 pts in this section) 1) Provide the products for the following sequence (9 pts): 0 ° NaOH ‘9 W ‘t 1 H20 \ ,l\(/»3M ,; f” Heat ’7 / fl, —> 00H3 * \———- 0* W 0 J) vL//5 0“ (fircWFSk/r/C 1) LiAIH4 ,ft. 1 ll » A \ /, /\OML “130+ well + mp” \\ O x 9 0H \ ../ j ,, B K . [N/\\ \\/,:/J 2) Provide the reagents for the following sequence (9 pts): Br 0 / ll 1) Mg L“ 3M SOCIZ —————> \) \ I ——> 2 co ° ’ 2 \gzfi 3) H30“ 11 CH 310 N EXAM #2 UTEID 3) Mechanism: Provide a mechanism for the following transformation. Show all important flows of electrons, charges and intermediates. Where indicated, (in the structure boxes)— draw the intermediates. (4 pt each structure-n—a-box; resonance structures, 2 pts ea) c0NH2 COOH HCI (aq) ——-> heat O \4 \ . \ ( , a '(D’ .' Iati\j\/(ZN\AL l?._ (va \A t \ /rl H a 2;») 'v . c l —'—> \ 4—» I»; 4———> /\ l \ ( \\ 4 \/ \/ Protonated Amide-must show 3 resonance structures for full credit Water attacks the Intramolecular Elimination of protonated amide proton transfer ammonla Acid Base reaction to give final products 12 j CH 310 N EXAM #2 UTEID 4) Provide a carbonyl compound and a corresponding Wittig reagent to prepare the following olefins. (15 pts ) l"2 A) c\ /CH3 C 0 + ,’ H2 2:) H N + H3C (in CH3 a; 9 Et B) 52’ r ’ , I I:> + M" )/\E k Ph H 6"“ 5 CHCH3 (9 A, I I:[> | 4, Q/\OM7 , c) Vin) 13 7\ CH‘31O N EXAM #2 UTEID J 5) For each transformation, provide the product (12 pts ) 0\’\ 1) LiAlH4 (./ H30+ O Zn-Hg 14 CH 310 N EXAM #2 UTEID 6) Provide the reagents required to bring about the following transformations (8 pts) COZH ‘OH ’7: / H 1 C " CH3 ) H / \ (H; MgBr ? _ <— (What reagents \ 4* can do this?) 2) H30 minim“ l/ L) Hgo‘ 0 1) N \/ 2) My“; L/ OH CH3 CH3 CH3 END OF EXAM SECTION / O 15 ...
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This note was uploaded on 06/07/2011 for the course CH 310M taught by Professor Iverson during the Spring '05 term at University of Texas.

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EXAM 2 COLAPRET - LASTNAME: HRSTNAME: | AHMAD COVERPAGE...

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