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Test Bank For Organic Chemistry, 7th Edition

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    BIAF 7e Test Bank 1 CHAPTER 1 — COVALENT BONDING AND SHAPES OF MOLECULES MULTIPLE CHOICE 1. How many electrons can the shell with a principal quantum number of 1 hold? a. 1 b. 2 c. 4 d. 8 ANS: B 2. How many electrons can the shell with a principal quantum number of 2 hold? a. 1 b. 2 c. 4 d. 8 ANS: D 3. What is the ground - state electronic configuration of a nitrogen atom (nitrogen: atomic number 7)? a. 1 s 2 2 s 1 2 p 4 b. 1 s 2 2 s 2 2p 3 c. 1 s 1 2 s 1 2 p 5 d. 1 s 2 2 s 2 2 p 2 ANS: B 4. What is the ground - state electronic configuration of a fluorine atom (fluorine: atomic number 9)? a. 1 s 1 2 s 1 2 p 7 b. 1 s 2 2 s 2 2 p 5 c. 1 s 2 2 s 2 2 p 6 d. 1 s 0 2 s 2 2 p 7 ANS: B 5. What is the ground - state electronic configuration of a fluoride anion (fluorine: atomic number 9)? a. 1 s 2 2 s 2 2 p 2 b. 1 s 2 2 s 2 2 p 5 c. 1 s 2 2 s 2 2 p 6 d. 1 s 2 2 s 2 2 p 7 ANS: C 6. What is the ground - state electronic configuration of a sodium cation (sodium: atomic number 11)? a. 1 s 2 2 s 2 2 p 6 3 s 1 b. 1 s 2 2 s 2 2 p 5 3 s 1 c. 1 s 2 2 s 2 2 p 6 d. 1 s 2 2 s 2 2 p 6 3 s 2 ANS: C

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    BIAF 7e Test Bank 2 7. Which of the following species has an atom that has an unfilled valence shell of electrons? a. molecular hydrogen, H 2 b. hydroxide anion, HO − c. boron trifluoride, BF 3 d. water, H 2 O ANS: C 8. Which of the following species has an atom that has an unfilled valence shell of electrons ? a. molecular bromine, Br 2 b. fluoride anion, F − c. ammonia, NH 3 d. aluminum trichloride, AlCl 3 ANS: D 9. Which of the following species possesses a formal charge? a. BH 3 b. BH 4 c. CCl 4 d. H 2 S ANS: B 10. Which of the following species po ssesses a formal charge? a. CCl 4 b. SiCl 4 c. AlCl 4 d. PCl 3 ANS: C 11. Which of the following compounds is an aldehyde? a. CH 3 CH 2 CH 2 COOH b. CH 3 CH 2 CHO c. CH 3 CH 2 CH 2 OH d. CH 3 CH 2 COCH 3 ANS: B 12. Which of the following compounds is an alcohol? a. CH 3 CH 2 COOH b. CH 3 CH 2 OCH 3 c. CH 3 CH 2 CH 2 OH d. CH 3 CH 2 CHO ANS: C 13. Which of the following compounds is a carboxylic acid? a. CH 3 CH 2 COOH b. CH 3 CH 2 OCH 3 c. CH 3 CH 2 CH 2 OH d. CH 3 CH 2 CHO ANS: A

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    BIAF 7e Test Bank 3 14. Which of the following compounds is a ketone? a. CH 3 CH 2 COOH b. CH 3 CH 2 CHO c. CH 3 CH 2 CH 2 OH d. CH 3 COCH 3 ANS: D 15. Which of the following compounds is a ketone? a. CH 3 CH 2 COOH b. CH 3 CH 2 CHO c. CH 3 CH 2 CH 2 OH d. CH 3 COCH 3 ANS: D 16. Which of the following compounds is a carboxylic ester? a. CH 3 CH 2 COOH b. CH 3 CH 2 OCH 3 c. CH 3 CH 2 COOCH 3 d. CH 3 CH 2 COCH 3 ANS: C 17. Which of the following is a tertiary alcohol? a. CH 3 CH 2 OCH 3 b. (CH 3 ) 3 COH c. (CH 3 ) 2 CHOH d. CH 3 CH 2 CH 2 OH ANS: B 18. Which of the following is a tertiary amine? a. CH 3 CH 2 N(CH 3 ) 2 b. (CH 3 ) 3 CNH 2 c. CH 3 CH 2 NHCH 3 d. CH 3 CH 2 NHCH(CH 3 ) 2 ANS: A 19. Which of the following is a primary amine? a. CH 3 CH 2 NHCH 3 b. CH 3 CH 2 NHCH(CH 3 ) 2 c. CH 3 CH 2 N(CH 3 ) 2 d. (CH 3 ) 3 CNH 2 ANS: D 20. Which of the following is trigonal planar? a. boron trifluoride, BF 3 b. methyl anion, CH 3 − c. methane, CH 4 d. ammonia, NH 3 ANS: A

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    BIAF 7e Test Bank 4 21. Which of the following molecules is not linear? a. H 2 O b. CO 2 c. HC  CH d. Cl 2 ANS: A 22. What is the approximate value of the H − C − H bond angles in methane, CH 4 ? a. 90  b. 109  c. 120  d. 180  ANS: B 23. What is the approximate C − C − C bond angle in propene, CH 3 CH=CH 2 ? a. 90  b. 109  c. 120  d. 180  ANS: C 24. What is the approximate C − C − C bond angle in propyne, HC  CCH 3 ? a. 90  b. 109  c. 120  d. 180  ANS: D 25. What is t he approximate H − C − O bond angle in formaldehyde, H 2 C=O? a. 90  b. 109  c. 120  d. 180  ANS: C 26. Which of the following elements has the highest electronegativity? a. N b. C c. O d. S ANS: C 27. Which of the following elements has the hi ghest electronegativity? a. C b. P c. Si d. Cl ANS: D

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    BIAF 7e Test Bank 5 28. Which of the following bonds is the most polar? a. F − F b. H − F c. C − H d. C − Si ANS: B 29. Which of the following bonds is the most polar? a. O − H b. C − H c. C − C d. H − H ANS: A 30. Which of the following bonds is a polar covalent bond? a. Na − F b. C − H c. C − O d. Cl − Cl ANS: C 31. Which of the following bonds is a polar covalent bond? a. Na − Cl b. C − Cl c. C − H d. Cl − Cl ANS: B 32. Which of the following is an ionic bon d? a. Br − Br b. C − Cl c. C − S d. Na − O ANS: D 33. Which of the following is an ionic bond? a. F − F b. C − H c. Li − O d. C − N ANS: C 34. Which of the following bonds has the smallest dipole moment? a. C − N b. C − O c. C − F d. O − H

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    BIAF 7e Test Bank 6 ANS: A 35. Wh ich of the following bonds has the smallest dipole moment? a. Li − Cl b. C − H c. O − H d. H − Cl ANS: B 36. Which of the following molecules has a molecular dipole moment? a. 1 b. 2 c. 3 d. 4 ANS: B 37. Which of the following molecules has a molecular dipole moment? a. 1 b. 2 c. 3 d. 4 ANS: B 38. Which of the following molecules has a molecular dipole moment? a. CO 2 b. BF 3 c. NH 3 d. CH 4 ANS: C 39. Which of the following molecules has a molecular dipole moment? a. H 2 O b. CO 2 c. HC  CH d. Cl 2 ANS: A

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    BIAF 7e Test Bank 7 40. Which of the following best represents the shape of the 2 s atomic orbital of carbon? a. 1 b. 2 c. 3 d. 4 ANS: A 41. Which of the following best represents the shape of a 2 p atomic orbital of carbon? a. 1 b. 2 c. 3 d. 4 ANS: B 42. Which of the following best represents an sp 2 hybridized atomic orbital of carbon which overlaps with the 1 s atomic orbital of hydrogen to form a C − H  bonding molecular orbital in ethene, H 2 C=CH 2 a. 1 b. 2 c. 3 d. 4 ANS: C 43. Which of the following best represents an sp 3 hybridized atomic orbital containing the lone pair of electrons of ammonia, NH 3 ?

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    BIAF 7e Test Bank 8 a. 1 b. 2 c. 3 d. 4 ANS: C 44. Which atomic orbitals overlap to form the C=O bond of acetone, (CH 3 ) 2 C=O? a. C 2 sp 3 + O 2 sp 2 b. C 2 sp 2 + O 2 p c. C 2 sp 2 + O 2 sp 2 d. C 2 sp 3 + O 2 sp ANS: C 45. Which atomic orbitals overlap to form the C − O bond of dimethyl ether, (CH 3 ) 2 O? a. C 2 sp 3 + O 2 sp 2 b. C 2 sp 2 + O 2 p c. C 2 sp 2 + O 2 sp 2 d. C 2 sp 3 + O 2 sp 3 ANS: D 46. What is the approximate value of the length of the C=C bond in ethane, CH 2 =CH 2 ? a. 121 pm b. 134 pm c. 142 pm d. 154 pm ANS: B 47. What is the approximate value of the length of the C  C bond in ethyne, HC  CH? a. 121 pm b. 134 pm c. 142 pm d. 154 pm ANS: A 48. Which of the following statements is not true regarding resonance structures? a. All resonance structure s must have the same number of electrons b. Each atom in all of the resonance structures must have a complete shell of valence electrons c. All resonance structures must have the same arrangement of atoms d. All resonance structures must be valid Lewis structures ANS: B 49. Which of the following statements is not true regarding resonance structures? a. Each resonance structure is in rapid equilibrium with all of the other structures b. The resonance structures may have different energies c. All resonance structures must have the same arrangement of atoms d. All resonance structures must have the same number of electrons

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    BIAF 7e Test Bank 9 ANS: A 50. Which of the following statements is not true about the carbonate anion, CO 3 2 − ? a. All of the oxygen atoms bea r the same amount of charge b. All of the carbon - oxygen bonds are the same length c. The carbon atom bears the negative charge d. It is basic ANS: C 51. Which of the following statements is not true about the acetate anion, CH 3 CO 2 − ? a. The oxygen atoms bear the same amount of charge b. The two carbon - oxygen bonds are the same length c. The carbon atom bears the negative charge d. It is basic ANS: C 52. Rank the following in order of decreasing importance as a contributing resonance structure to the molecular structure of acetone, CH 3 COCH 3 (more important > less important) a. 1 > 2 > 3 b. 1 > 3 > 2 c. 2 > 1 > 3 d. 3 > 1 > 2 ANS: B 53. Which of the following resonance structures is the least important contributor to the resonance hybrid of the acetate anion, CH 3 COO − ? a. 1 b. 2 c. 3 d. 4 ANS: C

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    BIAF 7e Test Bank 10 54. How many electrons are there in the valence shell of the carbon atom of a methyl cation, CH 3 + ? a. 4 b. 5 c. 6 d. 7 ANS: C 55. How many electrons are there in the v alence shell of the carbon atom of the methyl anion, CH 3 − ? a. 2 b. 4 c. 6 d. 8 ANS: D 56. How many electrons are there in the valence shell of the oxygen atom of water? a. 2 b. 4 c. 6 d. 8 ANS: D 57. How many electrons are there in the va lence shell of the nitrogen atom of ammonia? a. 4 b. 5 c. 6 d. 8 ANS: D 58. What is the approximate value of the H − C − H bond angles in a methyl cation, CH 3 + ? a. 90  b. 109  c. 120  d. 180  ANS: C 59. What is the approximate value of the H − C − H bond angles in a methyl anion, CH 3 − ? a. 90  b. 109  c. 120  d. 180  ANS: B 60. Which atomic orbitals overlap to form the carbon - hydrogen  bonding molecular orbitals of ethane, CH 3 CH 3 ? a. C2 p + H1 s b. C2 sp + H1 s c. C2 sp 2 + H1 s d. C2 sp 3 + H1 s

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    BIAF 7e Test Bank 11 ANS: D 61. Which atomic orbitals overlap to form the carbon - hydrogen  bonding molecular orbitals of ethene, H 2 C=CH 2 ? a. C2 p + H1 s b. C2 sp + H1 s c. C2 sp 2 + H1 s d. C2 sp 3 + H1 s ANS: C 62. Which atomic orbitals overlap to form the carbon - carb on  and  bonding molecular orbitals of ethene, H 2 C=CH 2 ? a. C2 sp 3 + C2 sp 3 , and C2 p + C2 p b. C2 sp 2 + C2 sp 2 , and C2 sp 2 + C2 sp 2 c. C2 sp 2 + C2 sp 2 , and C2 p + C2 p d. C2 sp 3 + C2 sp 3 , and C2 sp 2 + C2 sp 2 ANS: C 63. Which atomic orbitals overlap to form the carbon - hydrogen  bonding molecular orbitals of ethyne, HC  CH? a. C2 p + H1 s b. C2 sp + H1 s c. C2 sp 2 + H1 s d. C2 sp 3 + H1 s ANS: B 64. Which atomic orbitals overlap to form the carbon - carbon  molecular bonding orbital of ethyne, HC  CH? a. C2 p + C2 p b. C2 sp + C2 sp c. C2 sp 2 + C2 sp 2 d. C2 sp 3 + C2 sp 3 ANS: B 65. Which of the following is a primary (1  ) alcohol? a. 1 b. 2 c. 3 d. 4 ANS: A

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    BIAF 7e Test Bank 12 66. Which of the following is a tertiary (3  ) alcohol? a. 1 b. 2 c. 3 d. 4 ANS: C 67 . Which of the following is a primary (1  ) amine? a. 1 b. 2 c. 3 d. 4 ANS: C 68. Which of the following is a secondary (2  ) amine? a. 1 b. 2 c. 3 d. 4 ANS: D 69. Which of the following is an carboxylic ester? a. 1 b. 2 c. 3 d. 4 ANS: A

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    BIAF 7e Test Bank 13 70. What is the approximate strength of the C − C bond of ethane? a. 376 kJ/mol (90 kcal./mol) b. 422 kJ/mol (101 kcal./mol) c. 556 kJ/mol (133 kcal./mol) d. 727 kJ/mol (174 kcal./mol) ANS: A 71. Which of the circled bonds is the strongest? a. 1 b. 2 c. 3 d. 4 ANS: A 72. Which of the following resonance structures makes the largest contribution to the structure of [H 2 CCHO] − ? a. 1 b. 2 c. 3 d. 4 ANS: B

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    BIAF 7e Test Bank 14 73. Which of the following shows curved arrows that correctly accounts for the differences between the two structures? a. 1 b. 2 c. 3 d. 4 ANS: C 74. Which of the following statements is not true? a. The sp 3 C − H bond of an alkane is weaker than the sp C − H bond of an alkyne. b. The carbon - carbon triple bond of an alkyne is shorter than the carbon - carbon bond of alkenes. c. The carbon - carbon triple bond of an alkene is exactly three times as strong as a carbon - carbon single bond of an alkane. d. The sp 3 C − H bond of an alkane is longer than the sp C − H bond of an alkyne. ANS: C 75. Which of the following is/are tetrahedral? 1. methane, CH 4 2. methyl carbocation, CH 3 + 3. methyl carbanion, CH 3 − 4. methyl radical, CH 3  a. only 1 and 2 b. only 1 and 3 c. only 1 and 4 d. only 2 and 3 ANS: B

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    BIAF 7e Test Bank 15 TRUE/FALSE 1. The following two structural formulas represent isomers. ANS: F 2. Consider the following structural formula. The following is a resonance structure. ANS: F 3. Overlap of the two atomic orbitals as shown could result in the formation of a  bond. ANS: T 4. Consider the following molecular model. The condensed structural formula would be ANS: T

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