PRACTICE FINAL EXAMINATION ORGANIC CHEMISTRY Which of the following compounds is a primary alcohol?
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1 PRACTICE FINAL EXAMINATION ORGANIC CEMISTRY Which of the following compounds is a primary alcohol? C2O O C3 O A. B. C. D. O 2. What is the name of the compound shown? O Cl A. trans-4-chlorocyclohexanol B. cis-4-chlorocyclohexanol C. trans-1-chloro-4-cyclohexanol D. cis-1-chloro-4-cyclohexanol 3. Which of the following statements about ethanol, C 3 C 2 O, is true? A. It contains one π bond. B. It contains six σ bonds. C. The C-O- bond angle is approximately 120. D. The -C- bond angles are approximately Which of the alkenes shown has the greatest heat of combustion? A. C 2 =CC 2 C 2 C 3 B. (C 3 ) 2 C=CC 3 C. C 3 D. C 3 C 2 C 3 \ / \ / C=C C=C / \ / \ C 2 C 3 127
2 5. Which of the compounds shown is isobutyl chloride? A. (C 3 ) 3 CCl B. C 3 CClC 2 C 3 C. (C 3 ) 2 CC 2 Cl D. C 3 C 2 C 2 C 2 Cl 6. What is the name of the compound shown? A. Bicyclo[4.1.0]heptane B. Bicyclo[3.1.1]heptane C. Bicyclo[3.2.0]heptane D. Bicyclo[5.4.0]heptane 7. Which of the following designations describes the compound at right? C 3 C 2 C(C 3 ) 2 A. E \ / B. Z C=C C. cis / \ D. trans C 3 8. What is the most important reason for the fact that cyclohexane is the most stable of the cycloalkanes of twelve carbons or less? A. There is eclipsing along two of the carbon-carbon bonds in the boat conformation. B. There is eclipsing along four of the carbon-carbon bonds in the chair conformation. C. Both torsional and bond angle strain are minimized in the chair conformation. D. Both torsional and bond angle strain are minimized in the boat conformation. 9. What is the relationship between the compounds shown? Cl Cl Cl Cl A. Same compound B. Enantiomers C. Diastereomers D. Structural isomers 10. Which of the following nucleophiles is the most reactive? A. C 3 COO B. C 3 COO C. C 3 O D. C 3 O 128
3 11. Which of these is the best method for preparing 1-bromopropane, C 3 C 2 C 2? CCl 4 A. C 3 C 2 C > light B. C 3 C 2 C > peroxides C. C 3 C=C > no peroxides D. C 3 C=C > 12. What is the relationship between the compounds shown? C3C2 C3C2 Cl C3 C C Cl C3 A. Same compound B. Enantiomers C. Diastereomers D. Structural isomers 13. What is the name of the compound shown? O C2C3 C(C3)2 A. 4-heptanol B. 2-methyl-3-hexanol C. 1-isopropyl-1-butanol D. 1-isopropyl-2-ethylethanol 14. Two structures are both superimposable on each other and the mirror images of one another. What is the relationship between them? A. Same compound B. Enantiomers C. Diastereomers D. Structural isomers 129
4 15. Which of the following reactions yields (C 3 ) 3 CCl? A. (C 3 ) 3 CO + Cl ---> CCl 4 B. (C 3 ) 2 C=C 2 + Cl > C. (C 3 ) 2 CC 2 O + SOCl 2 ---> CCl 4 D. (C 3 ) 3 C + Cl > 16. Which of the following acid-base reactions occurs as shown? A. C 3 COONa + C C ---> C 3 COO + C CNa B. C 3 ONa + C C ---> C 3 O + C CNa C. NaO + C C ---> 2 O + C CNa D. C 3 NNa + C C ---> C 3 N 2 + C CNa 17. What are the hybridizations of the carbon atoms numbered 1 and 2 in the structure shown? 1 2 A. sp2, sp3 B. sp2, sp2 C. sp, sp3 D. sp, sp2 18. Which of the following is NOT a meso compound? A. B. C. D. O O O O O O O O 130
5 19. What are the major products of the reaction shown? CCl4 C >? 3C 3C I II C3 III C3 IV A. I and III B. I and IV C. II and III D. II and IV 20. What is/are the major organic product(s) of the reaction shown? O Na + C3C2C2 --->? A. O + C2=CC3 B. + C3C2C2O C. OC2C2C3 D. OC(C3)2 21. What is the configuration of the molecule shown? C3 C2C3 C C A. 2S, 3S B. 2S, 3R C. 2R, 3S D. 2R, 3R 131
6 22. What is the major organic product of the reaction shown? B 3 TF 2 O 2, O (C 3 ) 2 C=CC > >? C 3 C 3 C 3 C 3 A. C 2 CC 2 C 3 B. C 3 CC 2 C 3 C. C 3 CCC 3 D. C 3 CC 2 C 2 O O O O 23. What is the relationship between the compounds shown? C2C3 C3 C3 O C3 O C3 C2C3 A. Same compound B. Enantiomers C. Diastereomers D. Structural isomers 24. Which of the following solutions can be used in a test to distinguish between the compounds C 2 =CC 2 C 3 and C 2 =CC 2 C 2? A. conc. 2 SO 4 B. 2 /CCl 4 C. AgNO 3 /ethanol D. KMnO 4 / 2 O 25. What is the best explanation for the relative stabilities of the gauche and anti forms of butane? The form has more strain. A. gauche... torsional B. gauche... steric C. anti... torsional D. anti... steric 26. What are the predicted shape and bond angle of formaldehyde, 2 C=O? A. Trigonal pyramid, B. Trigonal planar, C. Trigonal pyramid, 120 D. Trigonal planar,
7 27. Which of the following sequences can be used to make? 2SO4 C2I2 A. O > > heat Zn(Cu) KO C2I2 B. O > > heat Zn(Cu) 2SO4 CCl3 C > > heat KOC(C3)3 KO CCl3 D > > heat KOC(C3)3 28. An unknown alkene was subjected to ozonolysis, and the product of the reaction was the compound shown. What is the structure of the unknown? O C 3 O C 3 CC 2 CC 2 CC 3 C3 C3 C3 A. C3 B. C3 C. C3 D. C3 C3 C3 29. Which of the arrows gives the direction of the dipole moment of the molecule shown? C A. B. C. D. 133
8 30. Which of the following sequences gives cyclohexane from cyclohexanol? A. KO, alcohol, heat; then Zn, Cl B. Zn, Cl; then 2, Pd C. 2, Ni; then 2 SO 4, heat D. 2 SO 4, heat; then 2, Pt 31. Which of the following compounds is the least soluble in water? A. O B. O C. Cl D. Cl 32. What are the bases in the reaction shown? O + N2- O- + N3 I II III IV A. I and III B. I and IV C. II and III D. II and IV 33. What is the value of in kj mol-1 for the reaction below? Bond energies in kj mol-1 are: C 3 C 2 -O, 383; C 3 C 2 O-, 431; O-, 498; C 3 C 2 -OC 2 C 3, C 3 C 2 O ---> 2 O + C 3 C 2 OC 2 C 3 A. +29 B. -19 C. -67 D Which of the S N 2 reactions below is the FASTEST? A. C 3 + C C ---> C 3 C C + B. C 3 + C C ---> C 3 C C + C. C 3 C 2 + C C ---> C 3 C 2 C C + D. C 3 C 2 + C C ---> C 3 C 2 C C One of the two carbon-carbon bonding orbitals in ethylene, 2 C=C 2, is formed from the overlap of orbitals on the carbons, and the other is formed from the overlap of orbitals. A. sp, p B. sp2, p C. sp2, sp D. p, p 134
9 36. Rate data for the reaction shown Run Rel. is given in the table at right. no. [C 3 C 2 I] [C 3 O ] Rate What is the mechanism of this reaction? C 3 C 2 I + C 3 O ---> C 3 C 2 OC 3 + I A. S N 1 B. S N 2 C. E1 D. E2 37. Which of the carbocations shown do NOT rearrange? I. C 3 C 2 C 2 C 2 II. C 3 CC 2 C 3 III. (C 3 ) 2 CC 2 IV. (C 3 ) 3 C A. I and III B. I and IV C. II and III D. II and IV 38. Which of the following compounds has the highest boiling point? A. C 3 C 2 ONa B. C 3 C 2 OC 3 C. C 3 C 2 C 2 C 3 D. C 3 C 2 C 2 O 39. Which of the following is the best synthesis of cyclohexene from cyclohexane? A. KO, alcohol B. 2 SO 4, heat C. 2, light; then KO, alcohol D. 2, CCl 4 ; then 2 SO 4, heat 40. Which of the following is a sigma (σ) bonding orbital? Nuclei are indicated by solid dots, and the signs of the wave functions are shown A. - + B. C. D
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