PRACTICE FINAL EXAMINATION ORGANIC CHEMISTRY Which of the following species is formed during the mechanism of the reaction shown?
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1 PRACTICE FINAL EXAMINATIN RGANIC CEMISTRY Which of the following compounds is insoluble in both water and 5%, and soluble in both 5% Na and 5% NaC 3? N2 B. C2 C3 2. Which of the following species is formed during the mechanism of the reaction shown? -C- + (C 3 ) 2 CC > (C 3 ) 2 C-C- C 2.. C: B. C (C3)2CC (C3)2CC: 3. Which of the following is a step in the mechanism of the acid-catalyzed enolization of propanal, C 3 C 2 C? C 3 C 2 C + ---> 2 + C 2 C 2 C B. C 3 C C > + C 3 C 2 C C 3 C 2 C > + C 3 C 2 C + C 3 C 2 C > 2 + C 3 C 2 C + 4. What is the structure of the most stable enol form of the compound shown? B. 260
2 5. What is the name of the compound shown? C3 3,6-Dibromo-2-methylbenzene B. 2,6-Dibromo-1-methylbenzene 3,6-Dibromotoluene 2,5-Dibromotoluene 6. Which of the species shown is aromatic? B. N 7. Which of the following reactions gives trans-2-methylcyclohexanol as the major product? C2 B. C2 B3 TF 22, > > 3, > C3 C3 B3 TF 22, > > 3, > 8. Which of the compounds shown has the lowest boiling point? (C 3 ) 3 C B. C 3 C 2 C 2 C 2 C 3 C 2 C 2 C 3 (C 3 ) 2 CC 3 261
3 9. Consider the reaction (C 3 ) 2 CI + C 3 ---> (C 3 ) 2 CC 3 + I. What is the mechanism of the reaction? Use the data table at right. [(C 3 ) 2 CI] [C 3 ] rel. rate SN1 B. SN E E Which of the following compounds is an ester? C 3 CC 3 B. C 3 C 2 C CC 2 C 3 C 3 CC What is the structure of the conjugate base of the ion -C-N-? C-N: B. -C-N- -C-N- -C-N Which of the following reaction sequences can be used to convert C2C into C2C2C? LiAl 4, then 3 + ; P 3 ; Mg/ether, C 2, then 3 + B. S 2 ; (C 3 ) 2 CuLi; LiAl 4, then 3 + S 2 ; then NaCN, then 3 + /heat LiAl 4, then 3 + ; 2 Cr Which of the following acid-base reactions occurs as written? C 3 C 2 Na + C 3 C 2 ---> C 3 C 2 + C 3 C 2 Na B. Mg + C 3 C 2 ---> 2 + C 3 C 2 Mg C 3 + C 3 C 2 Mg ---> C 3 C 3 + C 3 Mg C 3 C 2 Na + C 3 C C ---> C 3 C 2 + C 3 C CNa 262
4 14. Which of the following compounds is the strongest acid? C C C C B. N2 C3 C3 15. Which of the following gives benzaldehyde from benzoic acid? LiAl 4 B. PCC (pyridinium chlorochromate) NaB 4, followed by Na 2 Cr 2 7 / 2 S 4 S 2, followed by 2 /Ni 2 B 16. Which of the following alcohols cannot be synthesized using the reaction sequence shown? G Mg C2 C > > > ether C3 C2C2 B. N C C2C2 C2C2 C3 C2C2 17. Which of the following reagents can be used to distinguish between 1-pentanol and 2-pentanol? I 2 /Na B. Cr 3 / 2 S 4 2 /C 4 2 / Which of the following reagents is used to carry out the transformation shown? C2C3? > C2C3 LiAl 4 B. NaB 4 Cr 3 / 2 S 4 PCC 263
5 19. In the Grignard synthesis of C 6 5 C-C 2 C 3, which of the following pairs of compounds C 3 can be used as starting materials? C 6 5 CC 2 C 3 and C 3 B. C 6 5 CC 3 and C 3 C- C 3 C 6 5 C- and C 3 CC 3 C 6 5 and (C 3 ) 2 C= 20. Which of the following reagents is used to give the transformation shown? C2C3? -----> CC3 2 /Fe 3 B. 2 /light 2 /P 2 / Which of the following compounds is the most reactive toward 2 /Fe 3? C3 C C3 N2 B. 22. The nitration of benzaldehyde yields predominantly: o-nitrobenzaldehyde. B. m-nitrobenzaldehyde. p-nitrobenzaldehyde. a mixture of the ortho and para isomers. 264
6 23. Which of the following free radicals is the most stable? C3 B. C3 C3 C3 24. What alkene is the major organic product of the dehydration of (C 3 ) 2 CC 2 C 2 with concentrated sulfuric acid? 3-methyl-1-butene B. 2-Pentene 2-methyl-1-butene 2-methyl-2-butene 25. Which of the following reagents can be used to distinguish between 1-pentene and 1-pentyne? 2 in C 4 B. Cold aqueous KMn 4 Chromic acid Silver nitrate in aqueous ammonia 26. What is the most stable conformation of cis-3-tert-butyl-1-methylcyclohexane? The methyl group is axial and the tert-butyl group is equatorial. B. The tert-butyl group is axial and the methyl group is equatorial. Both groups are axial. Both groups are equatorial. 27. What is the name of the compound at right? C 3 C 2 CC 3 N 2 n-butylamine B. Isobutylamine sec-butylamine tert-butylamine 28. What is the product of the reaction sequence shown? N > Fe3 Sn > NaN >, 0 3P >? N2 B. N2 N2 N2 265
7 29. Which of the following processes does not yield a primary amine? Ni C 3 -C-C 3 + N > Ni B. C 3 C 2 C N > 140 C Na, C2 5 C 3 CC N ---> > NaB4 C 3 C- + 2 N-C > > 30. What is the product of the reaction sequence shown? N > 2S4 Fe > NaN >, > 2? B. N2 N2 N2 31. ow many signals are present in the proton nmr spectrum of the compound shown? (Neglect signal splitting). C3 C3 1 B
8 32. What is the major organic product of the following reaction sequence? (C 6 5 ) 3 P NaN 2 C 6 5 CC 3 C 6 5 C > > >? C 6 5 C=C-C 3 C 6 5 B. C 6 5 C 2 C=CC 6 5 C 6 5 C=CCC 6 5 C 6 5 C 2 CC An unknown compound having the formula C 9 12 gave the following proton nmr spectrum. What is the structure of this unknown? doublet at 1.25 septet at 2.90 multiplet at 7.25 C3 C2C3 B. C3 C3 C3 CC3 C3 C2C2C3 34. Which of the following is the most important contributor to the resonance hybrid of the benzyl carbocation? C2 B. C2 C2 C2 267
9 35. What is the major organic product of the reaction shown? 80 C >? B. 36. What dienophile is used to synthesize the compound shown? C2C3 C2C3 C3C-C C-CC3 B. C3C-C=C-CC3 C2C3 C2C3 C2C3 C2C3 37. Which of the following compounds is soluble in concentrated 2 S 4, gives no reaction with either AgN 3 /alcohol or Ag(N 3 ) 2 +, and rapidly decolorizes 2 /C 4? C 3 C 2 C 2 - B. C 3 C C C 3 CC 3 C 3 C CC 3 268
10 38. Which of the following compounds is a product of the reaction shown? C 3 3 Zn/ 2 C 3 -C-C=C > >? C 2 =C- C 3 B. C 3 -C C-C 2 -C- -C- 39. Which of the following reactions does not occur as shown? C 3 -C=C > C 3 CC 3 B. C 3 -C=C > C 3 CC R-C- ---> > cold, + KMn > 40. Which of the compounds shown does not have a plane of symmetry? B. 269
11 41. What is the relationship between the structures shown? C3 C3 C3 Same compound B. Enantiomers Diastereomers Structural isomers C3 42. What is the configuration of the compound shown? C3 C C C2C3 2R, 3R B. 2R, 3S 2S, 3R 2S, 3S 43. Which of the following compounds has the smallest dipole moment? F \ / \ / BF 3 B. CF 3 C=C C=C / \ / \ F F F 44. What is the shape of the ion :C 3? Trigonal planar B. Tetrahedral Trigonal pyramidal Angular (bent) 45. What is the total charge of the species shown?.. C3N:.. 0 B
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