1. Whattypeofbondcleavagedoesthefollowingreactioninvolve?

A.homolytic
B.heterolytic

2. Whattypeofbondcleavagedoesthefollowingreactioninvolve?

3. PredictthesignofSofthefollowingreaction.

A.positive
B.negative
C.nochange
4. PredictthesignofSofthefollowingreaction.

A.positive
B.negative
C.nochange

5. PredictthesignofSofthefollowingreaction.

A.positive
B.negative
C.nochange

6. PredictthesignofSofthefollowingreaction.

7. PredictthesignofSofthefollowingreaction.

8. Whyistheentropychangenegativeforringclosures?
A.Closingaringresultsinfewermolecules.
B.Closingaringresultsinmoremolecules.
C.Closingaringreleasesenergy.
D.Closingaringrestrictstherotationaroundindividualcarboncarbonbonds.

9. WhichofthefollowingwouldyouexpecttohavethemostnegativeS?

10. Offollowingreactions,whichone(s)wouldyouexpecttohaveanegativeS?

11. PredictthesignofGforanexothermicreactionwithanincreaseinentropy.
A.positive
B.negative
C.nochange
D.cannotpredictwithoutadditionalinformation

12. PredictthesignofGforanendothermicreactionwithanincreaseinentropy.
A.positive
B.negative
C.nochange
D.cannotpredictwithoutadditionalinformation

13. PredictthesignofGforanexothermicreactionwithadecreaseinentropy.
A.positive
B.negative
C.nochange
D.cannotpredictwithoutadditionalinformation

14. PredictthesignofGforanendothermicreactionwithadecreaseinentropy.
A.positive
B.negative
C.nochange
D.cannotpredictwithoutadditionalinformation

15. DoesareactionwithapositiveGfavorreactantsorproducts?

16. DoesareactionwithanegativeGfavorreactantsorproducts?

17. DoesareactionwithapositiveSandapositiveHfavorreactantsorproducts?

18. DoesareactionwithapositiveSandanegativeHfavorreactantsorproducts?

19. DoesareactionwithaKeq=10favorreactantsorproducts?

20. DoesareactionwithaHof14kJ/molandaSof150J/molKat298Kfavor
reactantsorproducts?
21. DoesareactionwithaHof20kJ/molandaSof10J/molKat298Kfavor
reactantsorproducts?

22. Giventhefollowingratelaw,whatistheorderofthereactionwithrespectto
MeI?

23. Giventhefollowingratelaw,whatistheorderofthereactionwithrespectto
tertbutyliodide?

24. Giventhefollowingratelaw,whatistheorderofthereactionwithrespectto
sodiumcyanide?

25. Whatistheenergyofactivationforthefollowingreaction?
26. Whatistheenergyofactivationforthefollowingreaction?

27. Basedonthefollowingenergydiagram,isthereactionexothermicor
endothermic?

28. Basedonthefollowingenergydiagram,isthereactionexothermicor
endothermic?
 29. Whatistheeffectofacatalystonareaction?
A.Itincreasestherate.
B.Itdecreasestheentropy.
C.Itchangestheequilibrium.
D.Itmakestheproductsmorestable.

30. Whichofthefollowingdescribestheeffectofacatalystonareaction?
A.Itlowersthefreeenergyoftheproducts.
B.Itmakesthereactantslessstable.
C.Itchangestheequilibriumconstant.
D.Itlowerstheenergyofactivation.

31. Whichofthefollowingisanenergydiagramforathreestepreaction?

32. Whichofthefollowingisanenergydiagramforatwostepreaction?

33. Drawanenergydiagramforanendothermicreactionwithtwosteps.
34. Drawanenergydiagramforathreestepreaction.

35. Drawanenergydiagramforaconcertedexothermicreaction.
36. Whichofthefollowingenergydiagramsshowsaconcertedendothermicreaction?
Section6.6

37. Whichofthefollowingenergydiagramsshowsthereactionwiththesmallest
energyofactivation?

38. Whatisatransitionstate?
A.Anisolableintermediateinareaction.
B.Thestartingmaterialsofthereaction.
C.Alocalmaximumontheenergydiagram.
D.Alowenergypointbetweenthestartingmaterialsandtheproduct.

39. Whatisanintermediate?
A.Alocalmaximumontheenergydiagram.
B.Apointonthereactionpathwaythathasadiscretelifetime.
C.Apointhalfwaybetweenthestartingmaterialsandproducts.
D.Thehighestenergycompoundonanenergydiagram.

40. Whichofthefollowingenergydiagramsisofareactionwithonetransitionstate?

41. Whichofthefollowingenergydiagramsisofareactionwithoneintermediate?
 42. Identifythenucleophilicsiteinthefollowingmolecule.

43. Identifythenucleophilicsiteinthefollowingmolecule.

44. Identifythenucleophilicsite(s)inthefollowingmolecule.

45. Identifythenucleophiliccentersinthefollowingmolecule.

46. Identifythenucleophilicatominthefollowingmolecule.

A.P
B.C
C.H
D.Me

47. Identifytheelectrophilicsiteinthefollowingmolecule.

48. Identifytheelectrophilicsiteinthefollowingmolecule.

A.H
B.Cofcarbonyl
C.Cotherthancarbonyl
D.Oofcarbonyl

49. Identifytheelectrophilicsiteinthefollowingmolecule.

50. Identifytheelectrophilicsiteinthefollowingmolecule.

51. Identifytheelectrophilicsiteinthefollowingmolecule.

A.C
B.O
C.B
D.Noelectrophilicsite

52. Whichofthefollowingcannotbeanucleophile?

53. Whichofthefollowingcannotbeanelectrophile?

54. Whichofthefollowingishydride?
A.H+
B.H
C.H
D.H2

55. Drawthestructureofhydride.

56. Whichofthefollowingisthemoststablecation?
 57. Forthefollowingreactionstep,indicatewhichpatternofarrowpushingit
represents.

A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

58. Forthefollowingreactionstep,indicatewhichpatternofarrowpushingit
represents.

A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

59. Forthefollowingreactionstep,indicatewhichpatternofarrowpushingit
represents.

60. Forthefollowingreactionstep,indicatewhichpatternofarrowpushingit
represents.

A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

61. Forthefollowingreactionstep,indicatewhichpatternofarrowpushingit
represents.
A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

62. Forthefollowingreactionstep,indicatewhichpatternofarrowpushingit
represents.

A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

63. Forthefollowingreactionstep,indicatewhichpatternofarrowpushingit
represents.

A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

64. Melphalan,adrugusedinchemotherapy,reactswithitselfinthebodybefore
bindingwithitstarget,asillustratedinthemechanismbelow.Whichtwopatterns
ofarrowpushingareseeninthisreaction?

65. Melphalan,adrugusedinchemotherapy,reactswithitselfbeforebindingwithits
targetinthebody,asillustratedbelow.Drawinthecurvedarrowsthataccount
forthistransformation.
 66. Thefollowingreactionhasthreemechanisticsteps.Drawallcurvedarrows
necessarytocompletethemechanism.

67. Whatiswrongwiththefollowingmechanism?

A.Thereisnoleavinggroup,sothereshouldbenoarrows.
B.ThearrowshouldberemovingaprotonfromtheH2Ogroup.
C.Anarrowisalsoneededtoindicatethelossoftheleavinggroup.
D.Thearrowisbackwards.

68. Whatiswrongwiththefollowingmechanism?

A.Thereisnoleavinggroup,sothereshouldbenoarrows.
B.ThearrowshouldberemovingaprotonfromtheH2Ogroup.
C.Anarrowisalsoneededtoindicatethelossoftheleavinggroup.
D.ThearrowindicatingtheformationoftheCBrbond(nucleophilicattack)shouldstart
atthebromideanion.

69. Whichofthefollowingmechanisticstepsrepresentsanucleophilicattack?
 70. Whichofthefollowingmechanisticstepsrepresentsthelossofaleavinggroup?

71. Identifythesequenceofcurvedarrows(electronmovement)inthestepsofthe
followingreaction.

A.Protontransfer,protontransfer
B.Protontransfer,lossofleavinggroup
C.Nucleophilicattack,protontransfer
D.Protontransfer,nucleophilicattack

72. Thefollowingreactionhasthreemechanisticsteps.Identifythepatternofarrow
pushingstepsineachstep.
 73. Identifythesequenceofcurvedarrows(electronmovement)inthestepsofthe
followingreaction.

A.Protontransfer,protontransfer,nucleophilicAttack
B.Protontransfer,lossofleavinggroup
C.Nucleophilicattack,protontransfer,lossofleavinggroup
D.Protontransfer,nucleophilicattack,protontransfer

74. Identifythesequenceofcurvedarrows(electronmovement)inthestepsofthe
followingreaction.

A.Protontransfer,protontransfer,nucleophilicattack
B.Protontransfer,lossofleavinggroup,nucleophilicattack,protontransfer
C.Nucleophilicattack,protontransfer,lossofleavinggroup
D.Protontransfer,lossofleavinggroup,protontransfer,nucleophilicattack

75. Identifythesequenceofcurvedarrows(electronmovement)inthestepsofthe
followingreaction.

A.Protontransfer,protontransfer
B.Protontransfer,lossofleavinggroup
C.Nucleophilicattack,protontransfer
D.Protontransfer,nucleophilicattack

76. Whatpatternofcurvedarrowpushingisthesecondstepofthisreaction?
A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

77. Whatpatternofcurvedarrowpushingisthefourthstepofthisreaction?

A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

78. Whatpatternofcurvedarrowpushingisthesecondstepofthisreaction?

A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

79. Whatpatternofcurvedarrowpushingisthesecondstepofthisreaction?
A.Protontransfer
B.Lossofleavinggroup
C.Nucleophilicattack
D.Rearrangement

80. Whatpatternofcurvedarrowpushingisthesecondstepofthisreaction?

81. Drawarrowsforeachstepofthefollowingreaction.

82. Drawcurvedarrowsforeachstepofthefollowingreaction.

83. Drawcurvedarrowsforthefollowingmechanisticstep.
 84. Identifythenucleophilicandelectrophilicsitesinthereactantsofthefollowing
reaction.

85. Whichofthefollowingisthenucleophilicsiteinthereactantsofthefollowing
reaction?

A.Cofthecarbonyl
B.O
C.Li
D.MeofLiMe

86. Whichofthefollowingistheelectrophilicsiteinthereactantsofthefollowing
reaction?

A.Cofthecarbonyl
B.O
C.Li
D.Me

87. Identifythenucleophilicandelectrophilicsitesinthesubstrateandreagentofthe
followingreaction.

88. Whichofthefollowingistheelectrophilicsiteinthereactantsofthefollowing
reaction?
A.Cofcarbonyl
B.Oofcarbonyl
C.Cl
D.Oofalcohol

89. Whichofthefollowingcationsismostlikelytoundergorearrangement?

90. Willthefollowingcationundergorearrangement?

91. Willthefollowingcationundergorearrangement?

92. Willthefollowingcationundergorearrangement?

93. Willthefollowingcationundergorearrangement?

94. Whichofthefollowingisthemostlikelystructureofthefollowingcationafter
rearrangement?

95. Whichofthefollowingisthemostlikelystructureofthefollowingcationafter
rearrangement?
 96. Whichofthefollowingisthemostlikelystructureofthefollowingcationafter
rearrangement?

97. Drawthestructureofthemostlikelyfollowingcationafterithasrearranged.

98. Drawthemostlikelystructureofthefollowingcationafterithasrearranged.

99. Drawthemechanismandmostlikelyproductforthefollowingcation
rearrangement.

100. Drawthemechanismandmostlikelyproductforthefollowingcation
rearrangement.

101. Considertheproductofthefollowingmechanism.Howmanydistinct
resonanceswouldappearinthe(protondecoupled)13CNMRspectrumforthe
product?

A.2
B.3
C.4
D.5

102. Considerthefollowingreaction.Whatpatternsofarrowpushingare
likelyinvolvedintheformationoftheproduct?WouldyouexpecttheSforthe
reactiontobepositiveornegative?