Exam 2 Review

Page 1 Name: __________________________ 1. Which one is bicyclo[3.3.1]nonane? I II III IV V A) I B) II C) III D) IV E) V 2. Which molecule is a meso compound? H Cl BrCl HBr H ClH Cl Br Br Cl BrCl H Br Br I II III A) I B) II C) III D) More than one of these E) None of these Page 2 3. I and II are: NH2 I II NH2HO OH A) constitutional isomers. B) enantiomers. C) identical. D) diastereomers. E) not isomeric. 4. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule? A) 2 B) 3 C) 4 D) 5 E) 6 5. Which of the following can be described as trans isomers? CH3 CH2CH3 Cl CH3 BrHO CH3 HO Br F I II III IV V A) I B) II, V C) III, IV D) I, III and IV E) None of the above are trans isomers. Page 3 6. Which structure(s) represent(s) diastereomer(s) of I? CH3 OHH HHO HO H CH3 I II CH3 OHH HHO H OH CH3 CH3 OHH OHH H OH CH3 III IV CH3 HHO HHO H OH CH3 V CH3 OHH OHH HO H CH3 A) II B) II and III C) II and IV D) III and V E) IV and V 7. Draw a dash-wedge structure for (R)-5-methylhept-2-yne 8. A correct name for the following compound is: Br A) 4-bromo-3,8-dimethylbicyclo[5.2.2]nonane B) 3,8-dimethyl-4-bromo-bicyclo[5.2.0]nonane C) 4-bromo-3,8-dimethylbicyclo[5.2.1]decane D) 7-bromo-2,6-dimethylbicyclo[5.2.0]nonane E) 4-bromo-3,8-dimethylbicyclo[5.2.0]nonane 9. Which of the following represent (R)-2-butanol? H CH2CH3 OHH3C I CH3 CH2CH3 OHH II H CH2CH3 CH3HO III CH3 CH2CH3 HHO IV CH2CH3 CH3 OHH V A) III and V B) I, III, IV and V C) I, IV and V D) I and III E) I, II, IV and V Page 4 10. The molecules below are: H CH3 H Cl H Cl H CH3 A) constitutional isomers. B) enantiomers. C) diastereomers. D) identical. E) None of these 11. The least stable conformation of 2,3-dimethylpentane, viewed through the C-2?C-3 bond (i.e., C-2 in the front, C-3 in the back): H HH3C CH3 CH2CH3H II CH3H CH3 CH3 CH2CH3H I CH3H CH3 CH(CH3)2 HH3C V III IV H CH3H3C CH3 CH2CH3H H CH3H3C H CH2CH3H3C A) I B) II C) III D) IV E) V Page 5 12. trans-1,2-Dibromocyclohexane is represented by structure(s): Br H Br H H Br Br H Br H H Br I II III A) I B) II C) III D) II and III E) I and II 13. Pairs of enantiomers are: CH2CH2CH3 H3C Cl CH3 CH2CH2CH3 Cl CH3 CH3 I II H H3C Cl CH2CH2CH3 CH2CH2CH3 H H CH2Cl IV V CH2CH2CH3 H3C Cl H III A) I, II and III, IV B) I, II C) III, IV D) IV, V E) None of the structures 14. I and II are: I II ClOH Cl OH A) constitutional isomers. B) enantiomers. C) identical. D) diastereomers. E) not isomeric. Page 6 15. Which molecule has a plane of symmetry? F Cl HCl HH H CH3 Cl H H CH3 CH3 H I II III A) I B) II C) III D) More than one of these E) None of these 16. Consider the graph below, which is a plot of the relative energies of the various conformations of 2,3-dimethylbutane, viewed through the C-2?C-3 bond. The conformations corresponding to the 120o and 240o are: 0o 60o 120o 180o 240o 300o 360o Re lat ive en erg y Angle of rotation A) Eclipsed, more stable than the conformation at 0o B) Eclipsed, more stable than the conformation at 180o C) Staggered, more stable than the conformation at 0o D) Staggered, less stable than the conformation at 180o E) Two of the above are true 17. How many moles of hydrogen (H2) will react with (trans, trans)-hepta-3,5-dien-1-yne? A) 1 2 B) 2 C) 3 D) 4 E) 5 Page 7 18. CH3CHBrCHBrCHClCH3 is the generalized representation of what number of stereoisomers? A) 4 B) 5 C) 6 D) 7 E) 8 19. A correct IUPAC name for the following compound is: OH Cl A) 4-propyl-5-chloro-3-heptanol B) 4-propyl-3-chloro-5-heptanol C) 4-(1-chloropropyl)-3-heptanol D) 5-chloro-4-propyl-3-heptanol E) 3-hydroxy-4-propyl-5-chloroheptane 20. In the most stable conformation of cis-1,4-dimethylcyclohexane, the methyl groups are: A) one axial, one equatorial. B) both axial. C) both equatorial. D) alternating between being both axial and both equatorial. E) None of the above rap0010 Microsoft Word - Test 2 Review.rtf