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ANSW_KEY_PROB_SET_3 - 7 CEM 351 Fall 2008 Prof Rathke...

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Unformatted text preview: 7) CEM 351 Fall 2008 - Prof. Rathke -- Answers -- 3rd Sample Problem Set (Chapters 10, 11, 12, 13) Draw the structure of the following molecules: cis3-phenylcyclopentanol 3-methyl-2—butanol ethyl t-butyl ether isopropyl alcohol 2-ethoxy-2—phenylbutane trans-2-butene oxide 2—ethyloxirane CEM 351 — Dr. Rathke, Fall 2008 — Answers — 3rd Sample Problem Set.... page 2 8) N-ethyl-2—butanamine 9) triethylamine 10) benzyl alcohol CH CH CH \3020/ 3 \30_C ¢ / _ A B 11. Which of the above configurational isomers (A or B) will be the major elimination product of the following sequences (assume all steps exhibit 2nd order kinetics): 1) socrz / 2) AKOH HO ‘4) (E2) Answer \ ~‘L‘CH3 (E2) Answer Draw the structures of the major organic products of the following Redox reactions: 12) Mal-l 3. H20 4 Q CEM 351 — Dr. Rathke, Fall 2008 * Answers — 3rd Sample Problem Set.... page 3 13) 0 H (OD/CH2 C_OH 1) LiAlH4 (excess) CA-l. ;._ DH. :fiDH 2) acid @ 14) O 1) NaBH DH G 4 Cl’03 2) acnd k; H2804, Q CH3 CH 3 H2O c; R 3 Draw the structure of the major organic products for each of the following reactions: 15. 0 /\/CH3 1) NaOCH3 ch—c —-.—> \ 2 aCId CH3 ) 16. o \ /CH3 CH3OH H20—0\ sto4 CH3 17. CH\3 CH—O—CHZCH3 L, / excess CH3 18. CH3 CH—CHCH3 _—.A C—“g c_—_—_Q_C.l.k3 I | excess NaNH2 Cl CI Elimination product CEM 351 — Dr. Rathke, Fall 2008 — Answers — 3rd Sample Problem Set.... page 4 19. $H3 N HCI —> H20 20. 1) M9 CH3CHzBr ether C “3, (*1 M53 r H20/ \CH2 2) acid 21. CI / CM 3 0/ (CH3)ZCuLi LET C' e) —> 02 CuLi Q Draw structures to complete the following: 23. L, hu CHZCHZCchHs ‘ r —C.l~\ C“ LC“ LL“ 3 major monobromination product 24. CH3 Br2 CH3 —> hu CH3 _ major monobromination product 28. CEM 351 — Dr. Rathke, Fall 2008 — Answers — 3rd Sample Problem Set... page 5 25. ET NBS, hu ‘ —> O QNBr 0 major monobromination product 26. C13 HBr if“? \ CH—CH=CH _ .. _ Cg 2 peroxides ,u [k '43“ cf“ 2' 3 0A a r organic radical intermediate major organic product 27. no peroxides Ht carbocation intermediate major organic product Assume each step of the following reactions exhibits 2nd order kinetics and draw appropriate structures in the boxes: substitution oroduct CEM 351 - Dr. Rathke, Fall 2008 — Answers — 3rd Sample Problem Set.... page 6 C) —> KOH d) OH c" x“ _> ——> CH CH PCIS KOH 2 3 C \ ii 1 avg , ma'or elimination roduct 013— [CH3 0'33 /¢ /C_C\ ,C=C\ H a! H CH3 A B 29. Which of the above configurational isomers (A or B) will be the major elimination product of the following sequences (assume all steps exhibit 2nd order kinetics): 1) SOCI2 —> 2) A, KOH HO\ ‘4, (E2) Answer “C_C“ACH3 H“/ \H CH3 \ 1) CH3—@—8020i 2) A, KOH Answer (E2) CEM 351 - Dr. Rathke, Fall 2008 — Answers — 3rd Sample Problem Set... page 7 30. Draw the structure of the major organic product: CH 3 A N“. W3 a) —> r H2504 OH > “i” A , b CH3CH2CHCH3 H2504 CH3CH " CH C43 31. lR indicates —OH. Molecular formula indicates no rings or double bonds. 1HNMR suggests two methyl groups. This is enough to draw a complete structure: CH3CHCH3 I OH o 32. CH30HQCH C—OH I \J 511.6 CI 0 33. /C©O—CHZCHZCH3 H k 69.8 it 34- CHSCH—C—O—CHa | OH Br BrICI) I l @i—i—c—cm H H 36. 37. 38. 39. 40. 41. CEM 351 — Dr. Rathke, Fall 2008 — Answers — 3rd Sample Problem Set.... page 8 0 CH9: ll /CH—O—C—CH2—?H2 CH3 CI IR suggests — NH2, molecular formula shows no rings or double bonds. 1HNMFl signal at 62.9 must be for 1 H on the carbon attached to —NH2. '. CH3CH2—(l3H—CH3 NH2 0 O II II CH3C—CH20H2_CCH3 \—V—’ can't couple because identical 0 A Ph Br /\/\ OCHZCH3 if 0 HO—CH2CH2C ECCH2CH3 CEM 351 — Dr. Rathke, Fall 2008 — Answers — 3” Sample Problem Set.... page 9 42. Vov O o 43. /\O/U\/J\O/\ O 45. Deduce the structure of X (C11H14O) IR spectrum: 17200M'1, strong 1HNMFI spectrum: 6 7.2, singlet (5H) 6 2.4, triplet (2H) 6 2.3, quartet (2H) 6 2.2, triplet (2H) 6 1.0, triplet (3H) X (C11H14O) CEM 351 — Dr. Rathke, Fall 2008 — Answers — 3rd Sample Problem Set... page 10 46. Give the expected multiplicity (i.e. singlet, doublet, etc...) of the 1HNMR signal for the encircled protons. Assume equality of all coupling constants: O H IOI l a ) CH30®CCH3 b) CH3CHQC®2 C H3 (pure sample, slow exchange) c) CHgOC ®Zc H200H3 )CH30®ZOCHZC H3 47. How many signals are expected in the broad—band decoupled 13CNMR spectrum of the following molecule? C Hag/C H3 48. The base peak (most intense signal) in the mass spectrum of compound 2 has a mass of 30. Which of the following structures is most consistent with this fact (encircle one). NH2 c H30 H20 H20 H20 H2 NH2 NH2 CH30 H20 H20HCH3 CH3CHQCHCHZCH3 CH;- HH; (Mm a“ 30) 49. Problems 37 and 38, Chapter 12, on UV-visible spectroscopy. ...
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