Organic Chem II Fall 2005 Test 1 part b

Organic Chem II Fall 2005 Test 1 part b - OM 1.C - PR EME...

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Unformatted text preview: OM 1.C - PR EME D41 Q1-22 are to be filled in on your Scantron sheet. P OM CHM 202F- Organic Chemistry II Sept 21, 2005 - PR EME D41 1.C Exam 1 OM Name (Please Print):______________KEY___________________ - PR EME D41 1.C Student I D: _______________________________________ OM Test For m 1. - PR EME D41 1.C To be properly graded, you must indic ate your correct Test Form number on your Scantron!! COM 100 pts total. 10 pages total. Check to make sure you have all pages. - PR EME D4 11. Q1-22 are to be filled in on your Sc antron sheet. - PR EME D4 11. COM Q23-30 are to be filled in on this exam. ___________________ (3 pts ea; 66 pts total) 11. COM Q1-22: - PR EM ED4 Q23-30: ___________________ (34 pts) PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM Tot al: _____________________ (100 pts) 1 1.C OM P - PR EME D41 Q1-22 are to be filled in on your Scantron sheet. - PR EME D41 1.C OM For eac h of the following compounds indicat e the number of 1H NMR and 13C NMR signals you would expect to see (ignoring splitting). d.5 d.5 1.C c.4 HO e.6 HO e.6 - PR EME D41 b.3 OM 2. # of 13C NMR signals a.2 1.C c.4 D41 b.3 - PR EME a.2 OM 1. # of 1H NMR signals c.4 COM 4. # of 13C NMR signals d.5 e.6 O SO2 C F3 c.4 d.5 e.6 c.6 d.7 e.8 11. b.3 - PR EME D4 a.2 11. b.3 O SO2 C F3 - PR EME D4 a.2 COM 3. # of 1H NMR signals 11. COM 5. # of 1H NMR signals b.5 Cl O - PR EM ED4 a.4 O - PR EM b.5 c.6 d.7 e.8 Cl O COM a.4 ED4 11. COM 6. # of 13C NMR signals O ED4 11. 7. # of 1H NMR signals b.7 c.8 d.9 e.10 c.8 d.9 e.10 COM - PR EM a.6 a.6 b.7 COM - PR EM ED4 11. 8. # of 13C NMR signals 11. 9. # of 1H NMR signals a.0 b.1 c.2 d.3 e.4 O 11. COM - PR EM ED4 O 10. # of 13C NMR signals a.0 b.1 c.2 d.3 e.4 PRE MED 411 .CO MPRE M ED4 O 2 O OM 1.C - PR EME D41 Q1-22 are to be filled in on your Scantron sheet. P O 1.C OM H+ C H3OH - PR EME D41 11. - PR EME D41 1.C OM Q11-15: The major product of the following reactions should contain whic h functional group(s ) an epoxide a weak ac id and an alc ohol an ether an ether and a pri mar y alcohol an ether and a secondary alc ohol COM - PR EME D41 1.C OM a. b. c. d. e. O 11. 1. C6H5M gBr - PR EME D4 12. - PR EME D4 11. COM 2 . H 3O + an epoxide an organometallic compound an ether a primary alc ohol a tertiar y alcohol - PR EM ED4 11. COM a. b. c. d. e. HI COM - PR EM ED4 11. COM O 13. a pri mary alcohol and a terti ary alkyl halide a tertiary alcohol and a primary alkyl halide a tertiary alcohol and a tertiary alkyl halide a primary alc ohol and a s econdary alkyl halide none of the above ED4 11. COM - PR EM ED4 11. a. b. c. d. e. - PR EM OH H 2S O4 a monosubstituted alkene a disubstituted alkene a trisubstitut ed alk ene a tetr asubstituted alkene a sulfonate est er` PRE MED 411 .CO MPRE M ED4 11. COM a. b. c. d. e. - PR EM ED4 11. COM 14. 3 1.C OM P 1.C OM - PR EME D41 Q1-22 are to be filled in on your Scantron sheet. - PR EME D41 15. 1 . Ts C l - PR EME D41 1.C OM 2 . C6 H 5O Na OH a secondary alcohol and an ether a teriary alcohol and a sulfonat e ester a symmetric al ether an unsymmetrical ether none of the above COM - PR EME D41 1.C OM a. b. c. d. e. b c d ED4 11. COM a - PR EME D4 11. COM - PR EME D4 11. 16. A downfield (! 9-10) singlet is obs erv ed in the 1H NMR s pectrum of: Which is the base peak in the MS shown at right? COM - PR EM 17. m/z 15 m/z 29 m/z 44 m/z 45 m/z 100 ED4 11. COM - PR EM ED4 11. a. b. c. d. e. m/z 92 m/z 77 m/z 57 m/z 43 m/z 15 11. COM - PR EM ED4 11. a. b. c. d. e. COM - PR EM 18. The bas e peak for 2-c hloro-2-methylpropane would be expected to be. a. b. c. d. e. heterolytic cleavage only homolytic cleav age only both heter olytic and homol ytic cl eavage the McLafferty rearrangement none of the above PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 19. Alc ohols whic h show a loss of water by MS do so by what mec hanis m? 4 e OM 1.C OM - PR EME D41 Q1-22 are to be filled in on your Scantron sheet. - PR EME OM 1.C D41 two singlets a singlet and a doublet a doublet and a septet two triplets and a singlet none of the above - PR EME a. b. c. d. e. D41 1.C 20. The 1H NMR spectrum of 2-fluoropropane would s how: D41 1.C OM 21. The 1H NMR spectrum of 1,3-dichloropropane would show: a triplet and a doublet of doublets a singlet and a doublet a doublet and a septet two singlets and a doublet none of the above - PR EME D4 11. COM - PR EME a. b. c. d. e. - PR EME D4 11. COM 22. Treat ment of 2-butanol with POCl3 in pyridine at O° C yields: an epoxide via an SN2 mechanis m an ether via an E1 mec hanis m an alk ene via an E1 mechanis m an alkene via an E2 mechanism none of the above PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM a. b. c. d. e. 5 P 1.C OM P - PR EME D41 Q23-30 are to be filled i n on thi s exam. D41 1.C OM (3 pts ea) Provide the missing information. For missing products, provide the major organic product. OM - PR EME 23. - PR EME D41 1.C HI I OH 24. - PR EME D41 1.C OM O Br COM OH 11. 1. M sC l/py ridi ne 25. 1. HO Li 2 . H+ - PR EM ED4 11. COM - PR EM ED4 11. COM O - PR EME D4 11. COM - PR EME D4 2 . N aB r + (C H3 C H2 CH 2 )2C uL i TH F - PR EM ED4 11. COM 26. COM - PR EM ED4 11. COM Br P hM gBr o r P hLi D2 O COM - PR EM ED4 11. 27. PRE MED 411 .CO MPRE M ED4 11. D 6 1.C OM P - PR EME D41 Q23-30 are to be filled i n on thi s exam. D41 1.C OM 28. (7 pts) Propos e a structure for a c ompound whose molecular formula is C6H12O2, whose 1H NMR dat a is as shown. - PR EME Strong I R abs orption around 1740 c m-1. - PR EME D41 1.C OM To receive full credit you must “assign” y our prot ons, in other words label the protons in your structure to indic ate whic h corresponds to which signal. ! OM D41 1.C 1.2 3.7 # hydrogens splitting 9 3 singlet singlet - PR EME HA HB Approximate integration (mm) 19 6 a O COM a PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EME D4 a 11. b - PR EME D4 11. COM O 7 OM 1.C P 11. COM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 Q23-30 are to be filled i n on thi s exam. - PR EME D4 29. (7 pts) Provide the structure for the compound whose 13C NMR is s hown above. COM The molecular formula is C6H12O. PRE MED ED4 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM OH 11. COM - PR EM ED4 11. COM - PR EME D4 11. It shows a strong broad I R absorption around 3400 cm-1. 8 1.C OM P - PR EME D41 Q23-30 are to be filled i n on thi s exam. Hc D41 1.C OM Hb - PR EME D41 1.C OM 30. (5 pts) The 1H NMR of the following compound is shown below. Assign the signals. The relative areas of the peaks going from left (!6. 0) to right (!2.95) is 1:1:1:2: 1. OH e - PR EME Ha OM Hd d - PR EME D4 11. COM - PR EME D41 1.C Hd a b 11. COM e PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EME D4 c 9 PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EME D4 11. COM - PR EME D4 11. COM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C Q23-30 are to be filled i n on thi s exam. 10 OM P ...
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