Organic Chem II Fall 2007 Exam 2

Organic Chem II Fall 2007 Exam 2 - _..— <>A...

Info iconThis preview shows pages 1–10. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

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

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

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

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

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

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

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

View Full DocumentRight Arrow Icon
Background image of page 8
Background image of page 9

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

View Full DocumentRight Arrow Icon
Background image of page 10
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: _..— <>A (b) anti-aromatic, or (c) 2. Indicate whether the following is aromatic, non-aromatic. l 3. Which of the following statements about the TI: molecular orbital description of cyclobutadiene is n_ot correct? a. Cyclobutadiene has a single bonding 1! molecular orbital \/ hf b. Cyclobutadiene has two electrons in nonbonding rt molecular orbitals/ '— @ Cyclobutadiene has one electron in an antibonding 1: molecular orbital which >< makes it antiaromatic d. Cyclobutadiene has two degenerate nonbonding Tl: molecular orbitals e. none of the above 4. Which of the following is n__ot a correct statement about the electrophilic substitution mechanism of benzene? Benzene functions as a nucleophilex/ The carbocation intermediate contains an sp3. hybridized carbon in the ring -/ Formation of a carbocation intermediate is the rate—detennining step ‘/ The addition product is a frequent minor product a. b. g: {1:11 ’e. Aromaticity is regained by loss of H+v’ _ \ "I '1 M9 tx' Q0” ;' " -. _ / t (“(151 WW"? - M— "1/0 (,2 5. Indicate the major product. CH2CH1CH2CH3 CH3 Alcl- Ell-13 Iv' Cfizi: © + CHBAEHCHECI - 3 H. @CflchCHa CH3 4+ \ on; V_ HCHQCI-Ig at“ C—CH3 ‘ @ @fl H3 11.1 b. II (6.111 d. IV e. V i Pr 6. Indicate the major product. iPr = isoprOpyl 7. List the following amides in decreasing order of reactivity towards acid-catalyzed hydrolysis. (c. g. from most reactive to least) a. 11>IV>III>I 1- b. III>I>IV>11 c. I>III>II>IV @ IV>II>1>III " -* e. 11>IV>I>III 8. Name the following. @ S-bromo—2-njtrotoluene b. 3—bromo—6—nitrotoluene c. o-nitro—m-bromotoluene d. 2—nitro—S—bromotoluene e. m—bromo—omiu-otoluene 9. Which of the following reacts most slowly during nitration? a. I b. 11 c. III d. IV e. V 10. Which of the following reacts most rapidly during nitration? a. I b. 11 V c. III d. IV 6. V 11. Which of the following is the most important contributor to the resonance hybrid formed when anisole (methoxybenzene) undergoes o-bromination? 0V? @ 1 b. 11 “ ( c. III ' d. IV e. V , ._ '. .- _I_/"} L" - 12. How many of the following substituents are ortho-para directors? J < 5 __..._ , L. ' \_ " / (c. 7chécncéixiii ~Ql—I_20H vi ~ Eh Q4; =CH2 Ham 7 ‘ .,/ .../. _- _.._.;" I ‘ E... ii- a. 0 b. 1 c. 2 d. 3 e. 4 or more (ix/l F” V g \ t 2’ 13. Which of the following monoalkylbenzens undergo nitration in HNOJPIZSQ1 to yield a product mixture with the highest ortho 1 para ratio? a. toluene b. ethylbenzene @rert—butylbenzene e. isopropylbenzene 1 ,x/ c. propylbenzene 14. Provide the major organic product of the reaction below. v ( o w 08% m, r v 0 o o a. b c O O O O o O O 0 51 Cl Et cl \ Et ‘\ 0 o O 0 on o @ O 8' O o a 0\ E C: \- Cl 0 o 15. Which is the best method for carrying out the follgwing reaction? ‘1 “mm x ‘- © "’ H % CfiacHICHICV-MCE ; 502432304 0 )6 engcnfiwang; soynzso“ a.I 13.11 (2.111 d.IV e.V 16. List the following in order of decreasing acidity. (e. g., from most acidic to least) X OH I. , II. cho K C' a.I>III>II b.II>III>1 (@mun d.I>II>III e.II>l>III 17. What is the his; method for the preparation of m-dibromobenzene from benzene? @r X nitrate; Sn/HCl;NaN02fI-IC1, 0°C; brominatc twice b. nitrate; Sn/I-ICl;NaN02/HC1, 0°C; H3P02; brominate twice X nitrate; SanCl;NaN02lI-IC1, 0°C; brominate twice; H3P02 >le brominate twice Bf @ nitrate; brominate; Sir/HG, OgiHCl, 0_°C; CuBr Br 2‘ Cu Jr 18. Provide the proper IUPAC name fol-3W0. Ph = C5H5 a. 3=mmhfiA=benz§4butafione W e. 3-methyl—5-phenylpentangne MW 3-methyl-S-phenylpentanal 19. on; - NENH 1414713 e. Hand 111 b. II c. III (1. I and II 20. Which functional group(s) isfare present in the antibiotic, amoxicillin? a. b. c. d. a. b. ester anhydride amide / _ earboxylic acid ‘j more than one of the above NH2 mu 0 H0 N . . . 0 amoxrcrllm 'a .- a X #0 H0 21. What is the IUPAC name for the following compound? (1% benzyl acetate methyl benzoate c. phenyl ethanoate @ benzyl ethanoate e. benzyl methylacetate 22. What is the IUPAC name for the following compound: FCH2CH2CONHCH2CH3 a. l-fluoropentanamide b. 1-fluoro-3-pentanamide Q), Q o. ethyl 3-fluoropropanamide ( # C a C r C_ {o ( Hag H a; d. N—ethyl-l -fluoropropanamide @ N—ethyl-B-fluoropropanamide 23. Which of the following is one of the steps in the mechanism of the following reaction? 0 EB 0 H H II R—C—OH + CH3OH —————“+ R-C—OCH3 + H20 ea _ o—H OH . || 9 1 R-c—OH + CH3O -————*-+ R—C*OH | OCH3 O 0 II II 9 R—C“OH + CH3OH —~H--+ R-c + 0H EB 63 Zfi—H OH - I R—C-0H + CH3 H #—> PFC—OH this bond should be pointing directly 17k l 4/ at the oxygen H—o-CH3 EB 7L 9 I d. O 0 || | R—C-OH + CH3OH —-*'—’ R—C—OH this bond should be pointing directly | / at the oxygen and the oxygen should HOCH3 by... q (Jr) (hearse ye. o o H e I \ thls oxygen should bear a neganve v Q l . "f w 24. The following represents a kinetically unfavorable step. It can be represented by: a. step 21 below only b. step b below only c. either step a or b below 0 x} / C) 25. Which of the following compounds is hydrolyzed most slowly (if at all) in aqueous \\ NaOH? ' a c- (x 0 Q/ 0 a' R—E—n-O —E—CH3 Q R—g —N-Hz 0' R—Jli-OCH24© 0 0 Q d' R__J;l_ocfi3 e‘ 11—3—13! *7 9 «kg 0 / \ \6 l“ L\ 26. Indicate the major product. Note: assume excess ethanol is used. J 'L \ a. \-o o———/ 0/ 1‘ a s N d‘ a o H’lcati 0 0A :9 ‘ rt?) 0/\ 0+ o/\ ._.___F,/"" (L |\ 27. The following compound can react with itself (under mild acidic conditions) to form a hemiacetal. Indicate the product. ' g 320 0H '1 HO on ex a? HOCH2CH2CH2CH2CH —> N. cagcngcnfiincn’ ‘03 a.Ib.IIc.111d.IV e.V v. engcmcaocn, Vi Agr / fl" 28. indicate the major product. 1. NaCN. HCN 2. “Cl. H20, heat + NHa 0H 0 H0 3- 0H Q OH c. 0 d 0“ e. 0 CN 0 0H 0 o "1” 29. Which would be most appropriate as the reduction in the following sequence, a Clemmensen @, Wolff-Kishner (b), or sodium borohydride (c)? X! £)(U\;-.rr3 “ O I-A‘J \J t o LHOCIizCHgOH (1 «0.3+ CEO 2. redaction 3. 1130+ 30‘. Indicate the major product. Assume trace @ [023, Iv, Hymns acid present. g" scifis Csz H v. 11. 0 o HICHE g + ? Nv‘czflg a ‘ __ _ “(s-fig ’3 9H ‘3. 'fi 5’ -- means I 13.11 0.111 d.IV e.V 31'- tic-0,35 C135 31. A compound (or compounds plural) reacts with methylmagnesitun bromide followed by acidification to form a product with the following 1H NMR data. Identify the compound(s). Note again, the NMR is of the product; your job is to identify the starting material(s). & O c. 0 0A 0 d. more than one of the above e. none one of the above 32. 1H NMR data and structures for two esters are shown below. Match each compound to its spectrum and determine which is hydrolyzed more completely when each of the esters is added to an aqueous solution with a pH of 10 and allowed to reach equilibrium. 1-m- a. X goes with G, Y goes with H, and}? is hydrolyzed more b. X goes with G, Y goes with H, andAHfis hydrolyzed more c. X goes with H, Y goes with G, and? is hydrolyzed more d. X goes with H, Y goes with G, and H is hydrolyzed more ‘/ 33. Starting from benzene, indicate the preferred fi synthesis of acetaminophen, the active ingredient in H0 NHCCH3 Tylenol. acetaminophen a. 1. H2304,HN03 2. H2, Pd 3. NaNO;,HC1,0°C 4. H30+,A 5.H2$O4,HNO3 6. separate isomers 1H2, Pd 8. ethanoyl chloride b. 1. H2304,HN03 2. H2, Pd 3. ethanoyl chloride 4.Br2,FeBr3 5. separate isomers 6. NaOH, A c. 1. H2304, HN03 2. H2, Pd 3. H2304, KING; 4. separate isomers 5. H2, Pd 6. NaN02, HCl, 0°C 7. H30": A 8. ethanoyl chloride d. 1. ethanamide,A1C13 2. H2804,HN03 3.separate isomers 4. H2, Pd 5. NaNOz, HCl, 0°C 6. H30+, A Your Answer( 1- 50}: AACDCDDADD ACDDECEEAE DECABBDBAA CUB Correct Answer : . . . . . . ..C. DBA.....D. ...C.CB.B. ..A ...
View Full Document

This note was uploaded on 10/09/2011 for the course CHM 202H/F taught by Professor Heller during the Fall '11 term at FIU.

Page1 / 10

Organic Chem II Fall 2007 Exam 2 - _..— &amp;lt;&amp;gt;A...

This preview shows document pages 1 - 10. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online