Alkyl Halides Reactions Ch.7 Test Bank

Organic Chemistry, 4e (Klein)

Chapter 7 Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

1) Which of the choices is a substitution reaction?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

2) Which of the choices is a substitution reaction?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

3) Which of the choices is a substitution reaction?

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

4) Which of the choices is an elimination reaction?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

5) Which of the choices is an elimination reaction?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

6) What is the nucleophile in the reaction shown?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

7) What is the electrophile in the reaction shown?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

8) What is the nucleophile in the reaction shown?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

9) What is the electrophile in the reaction shown?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

10) What are the nucleophile, electrophile, and leaving group in the reaction shown below?

A) Nucleophile 2-chlorobutane; electrophile NaOH; leaving group Cl

B) Nucleophile 2-chlorobutane; electrophile Cl; leaving group NaOH

C) Nucleophile Cl; electrophile NaOH, leaving group 2-chlorobutane

D) Nucleophile NaOH; electrophile 2-chlorobutane; leaving group Cl

E) Nucleophile 2-chlorobutane; electrophile NaOH, leaving group Cl

Diff: 2

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

11) What are the nucleophile, electrophile, and leaving group in the reaction shown below?

A) Nucleophile bromo-2-propene; electrophile cyclohexoxide; leaving group Br

B) Nucleophile cyclohexoxide; electrophile bromo-2-propene; leaving group Br

C) Nucleophile Br; electrophile bromo-2-propene, leaving group cyclohexoxide

D) Nucleophile cyclohexoxide; electrophile Br; leaving group bromo-2-propene

E) Nucleophile Br; electrophile cyclohexoxide; leaving group bromo-2-propene

Diff: 2

Learning Objective: 7.1 Discuss the role a halogen plays in substitution and elimination reactions

12) Which of the choices is a primary alkyl halide?

A) (CH3)2CHCH2Cl

B) (CH3)2CClCH2CH3

C) (CH3)2CHCHClCH3

D) (CH3)2CHCH2CCl(CH3)2

Diff: 1

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

13) Which of the choices is a secondary alkyl halide?

A) (CH3)2CHCH2Cl

B) (CH3)2CClCH2CH3

C) (CH3)2CHCHClCH3

D) (CH3)2CHCH2CCl(CH3)2

Diff: 1

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

14) Which of the choices is a tertiary alkyl halide?

A) (CH3)2CHCH2Cl

B) (CH3)2CClCH2CH3

C) (CH3)2CHCHClCH3

D) (CH3)2CHCH2CHClCH2CH3

Diff: 1

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

15) Which of the choices is a secondary alkyl halide?

A) 1-Bromo-2-methylpropane

B) 2-Bromopropane

C) 1-Bromobutane

D) 2-Bromo-2-methylpropane

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

16) Which of the choices is a tertiary alkyl halide?

A) 1-Bromo-2-methylpropane

B) 2-Bromopropane

C) 1-Bromobutane

D) 2-Bromo-2-methylpropane

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

17) What is the classification for the halide shown?

A) primary halide

B) secondary halide

C) tertiary halide

D) quaternary halide

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

18) What is the IUPAC name for the compound shown?

A) 3-Fluorobutane

B) 2-Fluorobutane

C) (S)-2-Fluorobutane

D) (R)-2-Fluorobutane

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

19) What is the IUPAC name for the compound shown?

A) Chlorocyclopentane

B) 2-Chloro-1-methylcyclopentane

C) 1-Methyl-2-chlorocyclopentane

D) 1-Chloro-2-methylcyclopentane

Diff: 1

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

20) What is the IUPAC name for the compound shown?

A) 2-Bromo-4-pentylhexane

B) (2S,4S)-2-Bromo-4,5-diethylheptane

C) 3,4-Diethyl-6-bromoheptane

D) 2-Bromo-4-methylhexane

E) (2R,4R)-2-Bromo-4,5-diethylheptane

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

21) What is the IUPAC name for the compound shown?

A) 1,2-bromocyclopentane

B) (1R, 2S)-1,2-dibromocyclopentane

C) (1S, 2S)-1,2-dibromocyclopentane

D) (1S, 2R)-1,2-dibromocyclopentane

E) (1R, 2R)-1,2-dibromocyclopentane

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

22) What is the IUPAC name for the compound shown?

A) 1-bromocyclobutane

B) 1,1-bromocyclobutane

C) 1,1,-dibromobutane

D) 1,1-dibromocyclobutane

E) dibromobutane

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

23) What is the IUPAC name for the compound shown?

A) 5-bromo-1-fluorohexane

B) 2-fluoro-5-bromohexane

C) 5-fluoro-2-bromohexane

D) bromofluorhexane

E) 2-bromo-5-fluorohexane

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

24) What is the IUPAC name for the compound shown?

A) (1S, 3R)-1-chloro-3-ethyl-3-methylcyclohexane

B) (1S, 3R)-3-chloro-1-methyl-1-ethylcyclohexane

C) (1R, 3S)-1-ethyl-1-methyl-3-chlorocyclohexane

D) (1R, 3S)-3-chloro-1-ethyl-1-methylcyclohexane

E) (1S, 3R)-3-chlorocyclohexyl-1-methylethane

Diff: 3

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

25) What is the correct structure for 2-bromo-3-methylbutane?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

26) What is the correct structure for 3-ethyl-1-iodocyclohexane?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

27) What is the correct structure for (2S,5R)-2-fluoro-5-methylnonane?

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

28) Which choice shows the structure of 1-chloro-4-isopropylheptane?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

29) Which choice(s) shows the structure of cis-1,2-dibromocyclopentane?

A) I

B) II

C) III

D) I and II

E) I, II, and III

Diff: 2

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

30) Which choice shows the structure of (4R,8S)-4-iodo-2,2,8-trimethyldecane.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.2 Assign an IUPAC (systematic) name and a classification (1°, 2°, or 3°) to an alkyl halide

31) Which of the following is a reasonable definition of a concerted reaction?

A) a reaction in which bond breaking occurs first

B) a reaction in which all bond-breaking and bond-forming occurs at the same time

C) a reaction in which bond forming occurs first

D) a substitution reaction

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

32) When drawing a curved arrow mechanism, the tail of the arrow starts at ________.

A) the bond that is being formed

B) the atom with the positive charge

C) the source of electrons that is being moved

D) the location to which the electrons are being moved

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

33) When drawing a curved arrow mechanism, the head of the arrow goes to ________.

A) the bond that is being formed

B) the bond that is being broken

C) the source of electrons that is being moved

D) the location to which the electrons are being moved

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

34) Which of the following is the rate equation for the SN2 reaction shown?

A) Rate = k[1-bromopropane]

B) Rate = k[NaCN]

C) Rate = k[1-bromopropane] [NaCN]

D) Rate = k[1-bromopropane]2

E) Rate = k[1-bromopropane]2 [NaCN]2

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

35) Which of the following is the rate equation for the reaction shown?

A) Rate = k[CH3CH2CH2CHBrCH3]

B) Rate = k[NaN3]

C) Rate = k[CH3CH2CH2CHBrCH3] [NaBr]

D) Rate = k[CH3CH2CH2CHBrCH3] [NaN3]

E) Rate = k[CH3CH2CH2CHBrCH3]2 [NaN3]

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

36) Assuming no other changes, what would be the effect on the rate of the SN2 reaction shown if the concentration of 1-chloro-3-methylbutane was doubled?

Consider the following SN2 reaction,

A) The rate would double.

B) The rate would triple.

C) The rate would quadruple.

D) The rate would be halved.

E) There would be no effect

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

37) Assuming no other changes, what would be the effect on the rate of the SN2 reaction shown if the concentration of NaN3 was doubled?

A) The rate would double.

B) The rate would triple.

C) The rate would quadruple.

D) The rate would increase by a factor of 6.

E) There would be no effect

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

38) Assuming no other changes, what would be the effect on the rate of the SN2 reaction shown if the concentrations of both 1-chloro-3-methylbutane and NaN3 were doubled?

A) The rate would double.

B) The rate would triple.

C) The rate would quadruple.

D) The rate would be halved.

E) There would be no effect

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

39) Assuming no other changes, what would be the effect on the rate of the SN2 reaction shown if the concentrations of 2-bromopentane is doubled and the concentration of CH3CH2COONa is halved?

A) The rate would double.

B) The rate would triple.

C) The rate would quadruple.

D) The rate would be halved.

E) There would be no effect

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

40) Which choice shows the correct curved arrow mechanism for the given SN2 reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

41) What is the predicted product of the SN2 reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

42) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

43) Which of the choices is a mechanism for an SN2 reaction?

A) I

B) II

C) III

D) IV

E) Both I & II

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

44) Predict the product for the SN2 reaction shown.

A) I

B) II

C) III

D) IV

E) I and II

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

45) Predict the product for the SN2 reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

46) Predict the product for the reaction shown.

A) I

B) II

C) III

D) IV

E) None of these

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

47) Predict the product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

48) Predict the product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

49) Which of the alkyl halides shown will undergo the fastest SN2 reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

50) Which of the alkyl halides shown is essentially unreactive in an SN2 reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

51) Rank the compounds shown from most to least reactive in an SN2 reaction.

A) I > IV > II > III

B) II > I > IV > III

C) III > IV > I > II

D) IV > I > II > III

E) IV > III > I > II

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

52) Rank the compounds shown from most to least reactive in an SN2 reaction.

A) I > IV > II > III

B) II > I > IV > III

C) III > IV > I > II

D) I > III > II > IV

E) IV > III > I > II

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

53) Which of the alkyl halides shown will undergo the slowest SN2 reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

54) Which potential energy diagram describes the SN2 reaction shown?

A) I

B) II

C) III

D) IV

E) None of the above

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

55) Which choice shows the transition state for the given SN2 reaction?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

56) Which choice shows the transition state for the given SN2 reaction?

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

57) What is the likely product of the SN2 reaction shown?

A) I

B) II

C) III

D) IV

E) None of these

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

58) What is the likely product of the SN2 reaction shown?

A) I

B) II

C) III

D) IV

E) None of these

Diff: 1

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

59) What is the likely product of the SN2 reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

60) What is the curved arrow mechanism for the first step of the SN2 reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

61) Predict the organic SN2 product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

62) Predict the product for the SN2 reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.3 Describe the details of an SN2 reaction mechanism, including the transition state, the effects of substitution, and stereochemical outcome

63) Describe a strong nucleophile.

A) an anion

B) a cation

C) a radical

D) a neutral compound

Diff: 2

Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions

64) Which of the choices is not a nucleophile?

A) OH-

B) NH3

C) CH3OH

D) NH4+

E) All of these

Diff: 1

Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions

65) Which of the choices is a strong nucleophile?

A) OH-

B) H2O

C) CH3OH

D) NH4+

E) All of these

Diff: 1

Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions

66) Which of the choices is a weak nucleophile?

A) OH-

B) H2O

C) CH3O-

D) NH4+

E) All of these

Diff: 1

Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions

67) Which of the structures shown is an aprotic solvent?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 1

Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions

68) Which of the structures shown is a protic solvent?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 1

Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions

69) What is an important difference between protic and aprotic solvents?

A) protic solvents stabilize anions only

B) aprotic solvents stabilize anions only

C) protic solvents stabilize cations only

D) aprotic solvents stabilize both cations and anions

E) protic solvents stabilize both cations and anions

Diff: 2

Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions

70) What set of reaction conditions would favor an SN2 reaction involving 2-bromo-3-methylbutane?

A) a weak nucleophile in a protic solvent

B) a weak nucleophile in an aprotic solvent

C) a strong nucleophile in a protic solvent

D) a strong nucleophile in an aprotic solvent

Diff: 1

Learning Objective: 7.4 Discuss the effects of nucleophilic strength and solvent identity in substitution reactions

71) Which solvent(s) would favor an SN2 reaction by a secondary alkoxide?

A) acetone

B) ethanol

C) water

D) propanol

E) ammonia

Diff: 2

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

72) Which choice is a good example of an aprotic solvent?

A) NH3

B) H2O

C) OH-

D) DMSO

E) EtOH

Diff: 1

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

73) Which of the following examples shows a mechanism for concerted elimination?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.5 Describe the characteristics of E2 reactions, including rate and substrate effects, and the differences between elimination and substitution reactions

74) Identify the type of elimination involved in an E2 mechanism.

A) alpha elimination

B) beta elimination

C) gamma elimination

D) delta elimination

E) omega elimination

Diff: 1

Learning Objective: 7.5 Describe the characteristics of E2 reactions, including rate and substrate effects, and the differences between elimination and substitution reactions

75) What can you predict about the stability of the structures shown?

A) I is predicted to be more stable than II.

B) II is predicted to be more stable than I.

C) I and II are predicted to be equally stable.

D) It is impossible to predict without more information.

Diff: 1

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

76) What can you predict about the stability of the structures shown?

A) I is predicted to be more stable than II.

B) II is predicted to be more stable than I.

C) I and II are predicted to be equally stable.

D) It is impossible to predict without more information.

Diff: 1

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

77) What can you predict about the stability of the structures shown?

A) I is predicted to be more stable than II.

B) II is predicted to be more stable than I.

C) I and II are predicted to be equally stable.

D) It is impossible to predict without more information.

Diff: 2

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

78) What can you predict about the stability of the structures shown?

A) I is predicted to be more stable than II.

B) II is predicted to be more stable than I.

C) III is predicted to be more stable than I.

D) II is predicted to be more stable than III.

E) I, II, and III are predicted to be equally stable.

Diff: 1

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

79) Which statement is true about the stability of cycloalkenes?

A) Highly substituted alkenes are less stable than unsubstituted alkenes.

B) Cis alkenes are more stable than trans alkenes.

C) It is stable for a bridgehead of a bicyclic system can include a trans bond in a small ring.

D) Bicyclic rings with 10 carbons in one of the rings can have a trans double bond at the bridgehead position.

Diff: 2

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

80) Is the structure shown stable?

A) Yes, because it is consistent with Bredt's rule.

B) Yes, because it consists of two joined rings.

C) Yes, because it has a trans double bond.

D) No, because the ring is too small.

E) No, because it has a cis double bond.

Diff: 2

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

81) Which type of alkene would be predicted to be the most stable?

A) A highly substituted cis alkene.

B) An unsubstituted cis alkene.

C) A highly substituted trans alkene.

D) An unsubstituted trans alkene.

E) An alkene bonded only to hydrogens.

Diff: 1

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

82) Which alkene is predicted to be the most stable?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

83) Why is it unnecessary to specify whether the double bond in a four-carbon ring is cis or trans?

A) Cis double bonds are unstable in such small rings.

B) Trans double bonds are unstable in such small rings.

C) Double bonds in rings are not classified as cis or trans.

D) Double bonds do not form in such small rings.

Diff: 1

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

84) Does the molecule below violate Bredt's rule?

A) Yes, because there is a trans double bond in a ring.

B) Yes, because the bond angles are too small.

C) Yes, because the molecule is not aromatic.

D) No, because the ring is sufficiently large.

E) No, because the double bond includes the bridgehead carbon.

Diff: 2

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

85) What characteristic would let you recognize that something might be a good protic solvent?

A) It has a bright color.

B) It has a low boiling point.

C) It has a low melting point.

D) It is hydrophobic.

E) It forms hydrogen bonds.

Diff: 2

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

86) When you run the same reaction using fluoride and then iodide as nucleophiles, you find that fluoride reacts more rapidly. What can you do to cause the reaction involving iodide to become faster than the reaction using fluoride?

A) Change the solvent from methanol to DMSO.

B) Change the solvent from DMSO to methanol.

C) Increase the concentration of both nucleophiles.

D) Use a stronger base.

E) Increase the concentration of the solvent.

Diff: 3

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

87) Which of the following statements is true of polar aprotic solvents?

A) They are capable of hydrogen bonding.

B) They can increase the rate of SN2 reactions by orders of magnitude.

C) They are relatively uncommon.

D) They favor SN1 reactions.

Diff: 1

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

88) Why do polar aprotic solvents favor SN2 reactions?

A) Hydrogen bonding stabilizes the reaction intermediates.

B) Hydrogen bonding stabilizes the leaving group.

C) Polar aprotic solvents can't stabilize anions and therefore nucleophiles are more reactive.

D) Protic solvents destabilize nucleophiles and that reduces the likelihood of reaction.

Diff: 1

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

89) Which of the following can be stabilized by polar protic solvents?

A) Cations

B) Anions

C) Neutral species

D) Both cations and anions

Diff: 1

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

90) You discover that the energy of activation for an SN2 reaction decreases when you change the solvent. What is the most likely reason for this finding?

A) You have substituted a polar aprotic solvent for a polar protic solvent.

B) You have substituted a polar protic solvent for a polar aprotic solvent.

C) You have substituted an impure solvent for a pure solvent.

D) You have substituted a pure solvent for an impure solvent.

Diff: 3

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

91) Which of the SN2 reactions below is expected to proceed the rapidly?

A) CH3CH2CH2Br + NaOH in DMSO

B) CH3CH2CH2Br + NaOH in acetone

C) CH3CH2CH2Br + NaOH in ethanol

D) A and B

E) B and C

Diff: 1

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

92) Why are SN1 reactions favored by polar protic solvents?

A) Polar protic solvents contribute leaving groups.

B) Polar protic solvents stabilize the nucleophile.

C) Polar protic solvents cannot form hydrogen bonds.

D) Polar protic solvents stabilize intermediates.

Diff: 1

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

93) If you dissolve NaCl in a polar protic solvent, what will happen?

A) Both Na+ and Cl- will be stabilized by interactions with the solvent

B) Only Na+ will be stabilized by interactions with the solvent

C) Only Cl- will be stabilized by interactions with the solvent

D) Neither Na+ nor Cl- will be stabilized by interactions with the solvent

Diff: 2

Learning Objective: 7.12 Describe the effects of different solvents in SN1 and SN2 reactions

94) Rank the structures shown from most to least stable.

A) I > II > III > IV

B) II > III > IV > I

C) III > IV > 1 > II

D) IV > I > III > II

E) I > IV > III > II

Diff: 2

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

95) Rank the structures shown from most to least stable.

A) I > II > III

B) III > II > I

C) II > III > I

D) II > I > III

E) I > III > II

Diff: 2

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

96) Which of the alkenes shown is more stable?

A) I

B) II

C) They are equally stable.

D) It is impossible to tell without more information.

Diff: 3

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

97) Rank the structures shown from most to least stable.

A) I > II > III

B) II > I > III

C) III > I > II

D) III > II > I

E) II > III > I

Diff: 3

Learning Objective: 7.6 Discuss the relationship between the structure and the stability of alkenes and cycloalkenes

98) Which choices shows the mechanism for the elimination reaction shown, assuming that it is a concerted reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

99) Show the mechanism for the elimination reaction shown, assuming that it is a concerted reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

100) Which of the structure(s) shown is the most reactive in an E2 reaction?

A) I

B) II

C) III

D) I and II are equally most reactive

E) II and III are equally most reactive

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

101) Which of the structures shown is the major product of the given elimination?

A) I

B) II

C) III

D) None of the above

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

102) Which of the structures shown is the major product of the given elimination?

A) I

B) II

C) III

D) None of the above

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

103) What would be the best base for performing the elimination reaction shown?

A) KOCH3

B) KOCH(CH3)2

C) KOC(CH3)3

D) this reaction is not an elimination reaction

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

104) Which of the following would be the best base for performing the elimination reaction shown?

A) KOCH3

B) KOCH(CH3)2

C) KOC(CH3)3

D) this reaction is not an elimination reaction

Diff: 3

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

105) What major product(s) will be yielded by the elimination reaction shown?

A) I

B) II

C) III

D) IV

E) I and IV

Diff: 3

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

106) What is the product of the following elimination?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

107) What is the product of the elimination reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

108) Which of the alkyl halides shown would yield the indicated product upon reaction with sodium ethoxide?

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

109) Which of the alkyl halides shown would not yield the indicated product upon reaction with sodium ethoxide?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

110) Which isomer(s) of 2-bromo-1,1,3-trimethylcyclohexane would be most reactive in an E2 elimination?

A) I

B) II

C) III

D) I and II

E) III and IV

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

111) Draw the major product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

112) Draw the major product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

113) Draw the major product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

114) Draw the major product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

115) What is the predicted major product of elimination reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

116) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

117) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

118) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

119) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

120) What is the predicted major product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

121) What is the mechanism for the following elimination?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

122) What is the mechanism for the elimination reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

123) Which of the choices shows the correct mechanism for the elimination reaction of 2-bromo-2,3-dimethylbutane with methoxide?

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

124) What is the mechanism for the E2 reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

125) What is the predicted product for the E2 reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.7 Describe the factors that affect the outcome of an E2 reaction, including regiochemistry and stereochemistry

126) What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-methylbutane?

A) weak nucleophile in a protic solvent

B) weak nucleophile in an aprotic solvent

C) strong nucleophile in a protic solvent

D) strong nucleophile in an aprotic solvent

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

127) Which of the steps shown would not occur in a substitution reaction?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

128) Which statement correctly describes the mechanism of the reaction shown below?

A) Bromine leaves, forming a carbocation

B) Na+ is added to Br

C) CN- is added, forming a carbocation

D) Na+ and CN- are added simultaneously

E) Br- leaves and CN- is added simultaneously

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

129) What is the curved arrow mechanism for the first step of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

130) Which description best explains the mechanism for the reaction shown?

A) Br- leaves, producing a carbocation. A rearrangement occurs, allowing SH- to add to the bottom vertex of the ring.

B) Br- leaves and SH- is added simultaneously, then a rearrangement occurs.

C) SH- is added, which forces Br- to leave. This allows rearrangement to take place.

D) Br- leaves, producing a carbocation. A rearrangement occurs, allowing SH- to add to the bottom vertex.

E) Rearrangement occurs, forcing Br- to leave. This allows SH- to add to the bottom vertex.

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

131) Which of the choices gives the rate equation for the following SN1 reaction?

A) Rate = k[H2O]

B) Rate = k[1-chloro-1-methylcyclohexane] [H2O]

C) Rate = k[chloride ion]

D) Rate = k[1-chloro-1-methylcyclohexane]

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

132) Which of the choices gives the rate equation for the following SN1 reaction?

2-chloro-2-methylpentane + NaI→

A) Rate = k[NaI]

B) Rate = k[2-chloro-2-methylpentane] [NaI]

C) Rate = k[chloride ion]

D) Rate = k[2-chloro-2-methylpentane]

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

133) Which of the following choices is a potential energy diagram for an exothermic SN1 reaction?

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

134) Which of the alkyl halides shown undergoes the fastest SN1 reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

135) Which of the alkyl halides shown undergoes the slowest SN1 reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

136) Rank the compounds shown from most to least reactive in an SN1 reaction.

A) I > IV > II > III

B) II > I > IV > III

C) III > IV > I > II

D) IV > I > II > III

E) IV > III > I > II

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

137) Rank the compounds shown from most to least reactive in an SN1 reaction.

A) I > IV > II > III

B) II > III > I > IV

C) III > II > I > IV

D) I > III > II > IV

E) IV > III > I > II

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

138) Which of the compounds shown will undergo the fastest SN1 reaction?

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

139) Which of the compounds shown undergo the fastest SN1 reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

140) Which of the statements given is true about the stereochemistry of SN1 reaction?

A) retention of configuration at the electrophilic center

B) inversion of configuration at the electrophilic center

C) 50:50 mixture of retention and inversion of configuration at the electrophilic center

D) slightly more inversion than retention at the electrophilic center

E) slightly more retention than inversion at the electrophilic center

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

141) What is the predicted product of the SN1 reaction shown?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

142) What is the predicted product for the SN1 reaction shown?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

143) What is the predicted product for the SN1 reaction shown?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

144) What are the predicted products for the SN1 reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

145) What are the predicted products for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

146) Predict the product(s) for the SN1 reaction shown.

A) II

B) III

C) IV

D) I and IV

E) II and III

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

147) Provide a curved arrow mechanism for the first step of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

148) What is/are the predicted product(s) for the reaction shown?

A) I

B) II

C) III

D) I and III

E) II and IV

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

149) What is/are the predicted product(s) for the SN1 reaction shown?

A) I

B) II

C) I and IV

D) II and III

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

150) What is/are the predicted product(s) for the SN1 reaction shown?

A) I

B) II

C) I and III

D) II and IV

E) None of these

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

151) What is the predicted curved arrow mechanism for the reaction shown?

Mechanism:

A) I

B) II

C) III

D) I and II are equally possible

E) II and III are equally possible

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

152) Which reaction mechanism accurately describes this reaction?

A) I only

B) II only

C) I is more common, but II is also a likely mechanism.

D) II is more common, but I is also a likely mechanism.

E) It is impossible to tell from the information given.

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

153) Which choice shows the correct first step of the curved arrow mechanism for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

154) Predict the product(s) of the reaction shown.

A) I

B) I and II

C) III

D) IV

E) III and IV

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

155) Which of the compounds shown will undergo rearrangement in an SN1 reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

156) Predict the major product for the SN1 reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

157) Which of the compounds given will undergo rearrangement during a solvolysis reaction?

A) 3-iodo-5-methylheptane

B) 3-iodo-2-methylheptane

C) 3-iodo-3-methylheptane

D) 3-iodoheptane

E) cis-1-iodo-3-methylcyclohexane

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

158) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

159) Which of the structures shown is the most reactive in an E1 reaction?

A) I

B) II

C) III

D) II and III are equally reactive in an E1 reaction.

E) I, II, and III are equally reactive in an E1 reaction

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

160) Which of the structures shown is most reactive in an E1 reaction?

A) I

B) II

C) III

D) II and III are equally reactive in an E1 reaction.

E) I, II, and III are equally reactive in an E1 reaction.

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

161) For the following dehydration, draw the structure of the intermediate carbocation.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

162) For the following dehydration, draw the structure of the intermediate carbocation.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

163) What is the predicted product for the following elimination with no rearrangement?

A) I

B) II

C) III

D) IV

E) II and III

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

164) What is the structure of the intermediate carbocation formed during the dehydration reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

165) What is the major organic product of the dehydration reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

166) What is the product of the dehydration reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

167) What error is in the dehydration reaction mechanism shown?

A) There is an arrow missing that should show the movement of electrons from the bond between H and SO3H and SO3H.

B) There is an arrow missing that should show the movement of a pair of electrons from O to the bond connecting it to C.

C) OH does not initiate the reaction in the first step.

D) O should not have a positive charge in the second structure.

E) This type of reaction does not produce a carbocation.

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

168) What error is in the dehydration reaction mechanism shown?

A) The reaction should begin with an arrow pointing from SO3H2 to OH, not from O H to SO3H2.

B) OH2 should not have a positive charge as oxygen is too electronegative to be stable in this form.

C) Water needs to be added to H bonded to the third structure so that the electrons of the bond can move to form a double bond at the upper right side.

D) The arrow pointing from O H to SO3H2 should point to S and not to H.

E) The arrow shown on the third structure should point to the positively charged carbon, not to the bond at the upper right side.

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

169) Assuming that the reaction below is exothermic, which of the energy diagrams shown could describe it?

A) A

B) B

C) C

D) D

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

170) Assuming that the reaction below is exothermic, which of the energy diagrams shown could describe it?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

171) Which pattern of arrow pushing is associated with the first step in any dehydration reaction?

A) proton transfer

B) loss of leaving group

C) rearrangement

D) it is impossible to know without more information

E) none of these patterns of arrow pushing are used in the first step of dehydration reactions

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

172) What are the steps of arrow pushing involved in the following mechanism?

A) proton transfer

B) loss of leaving group followed by proton transfer and then rearrangement

C) proton transfer and loss of leaving group

D) rearrangement and loss of leaving group

E) proton transfer, loss of leaving group, rearrangement, and then proton transfer

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

173) Will the following alcohol undergo rearrangement during a dehydration reaction?

A) Yes, it will definitely undergo rearrangement.

B) Rearrangement is possible, but will not always occur.

C) Rearrangement will occur about half of the time.

D) Rearrangement will not occur.

E) It is impossible to determine without more information.

Diff: 1

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

174) Will the following alcohol be likely to undergo rearrangement during a dehydration reaction?

A) Yes, it will undergo rearrangement.

B) Rearrangement is possible, but usually will not occur.

C) Rearrangement will occur about half of the time.

D) Rearrangement will not occur.

E) It is impossible to determine without more information.

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

175) What is the structure of a rearranged carbocation that does not have a four-membered ring in the following acid-catalyzed dehydration of the following compound?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

176) What is the predicted product of the elimination reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.8 Describe the details of SN1 reactions and E1 reactions, including their rate equations, mechanisms, energy diagrams, rearrangements, substrate effects, and stereochemical outcomes

177) Based upon the energy diagram shown, is this reaction an E1 or an E2 elimination?

A) E1 elimination

B) E2 elimination

C) It is impossible to determine from the diagram alone.

D) The diagram suggests that it is not an elimination reaction.

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

178) Based upon the following energy diagram, is this reaction an E1 or an E2 elimination?

A) E1 elimination

B) E2 elimination

C) It is impossible to determine from the diagram alone.

D) The diagram suggests that it is not an elimination reaction.

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

179) What substitution reaction mechanism is the compound shown most likely to undergo?

A) SN1

B) SN2

C) Either SN1 or SN2

D) None of these

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

180) What substitution reaction mechanism is the compound shown most likely to undergo?

A) SN1

B) SN2

C) Either SN1 or SN2

D) None of these

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

181) What substitution reaction mechanism is the compound shown most likely to undergo?

A) SN1

B) SN2

C) Either SN1 or SN2

D) None of these

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

182) What substitution reaction mechanism is most likely for the conversion shown?

A) SN1

B) SN2

C) Either SN1 or SN2

D) None of these

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

183) What substitution reaction mechanism is most likely for the conversion shown?

A) SN1

B) SN2

C) Either SN1 or SN2

D) None of these

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

184) What substitution reaction mechanism is most likely for the conversion shown?

A) SN1

B) SN2

C) Either SN1 or SN2

D) None of these

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

185) Which of the following is the strongest nucleophile in a polar protic solvent?

A) F-

B) Cl-

C) Br-

D) I-

E) All of these

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

186) Which of the choices is the weakest nucleophile in a polar protic solvent?

A) F-

B) Cl-

C) Br-

D) I-

E) All of these

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

187) Which of the choices is the strongest nucleophile in a polar protic solvent?

A) F-

B) Cl-

C) OH-

D) SH-

E) All of these

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

188) Which of the compounds shown has the best leaving group?

A) I

B) II

C) III

D) IV

E) All of these

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

189) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) I and III

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

190) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) I and II

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

191) What is the predicted product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

192) What is (are) the predicted product(s) for the following reaction?

A) I

B) II

C) III

D) I and II

E) I and III

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

193) By what mechanism is the reaction shown likely to occur?

A) SN1

B) SN2

C) E1

D) E2

E) It is impossible to tell from the information given.

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

194) By what mechanism is the reaction shown likely to occur?

A) SN1

B) SN2

C) E1

D) E2

E) It is impossible to tell from the information given.

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

195) By what mechanism is the reaction shown likely to occur?

A) SN1 (major) and/or E1 (minor)

B) SN2 (major) and/or E2 (minor)

C) E1 only

D) E2 only

E) It is impossible to tell from the information given.

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

196) By what mechanism is the reaction shown likely to occur?

A) SN1

B) SN2

C) E1 or E2

D) SN1 or E1

E) SN2 or E2

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

197) By what mechanism is the following reaction likely to occur?

A) SN1

B) SN2

C) E1

D) E2

E) It is impossible to tell from the information given.

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

198) What is (are) the most likely product(s) for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

199) What is (are) the most likely product(s) for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

200) What is the most likely product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

201) What is (are) the most likely product(s) for the following reaction?

A) I

B) II

C) I and III

D) II and III

E) I, II, and III

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

202) What is the most likely product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

203) What is the most likely product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

204) What is the most likely product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

205) What is the most likely product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

206) Which term best describes the most likely role of the given species in a substitution or elimination reaction?

A) nucleophile

B) base

C) it is equally likely to act as a nucleophile or as a base

D) it will not act as either a nucleophile or a base

E) it is impossible to tell from the information given

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

207) Which term best describes the most likely role of the given species in a substitution or elimination reaction? Is the following more likely a nucleophile or a base?

A) nucleophile

B) base

C) it is equally likely to act as a nucleophile or as a base

D) it will not act as either a nucleophile or a base

E) it is impossible to tell from the information given

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

208) Which of the choices is the strongest nucleophile?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

209) Which of the choices is the strongest nucleophile?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

210) Which of the choices is most likely to act as a base rather than a nucleophile?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

211) Which of the choices is most likely to act as a base rather than a nucleophile?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 7.9 Predict the products of reactions that may result in either substitution or elimination

212) Which reagents are appropriate to carry out the conversion shown?

A) NaCl in water

B) NaCl in ether

C) HCl in water

D) TsCl/pyridine followed by NaCl

Diff: 2

Learning Objective: 7.10 Determine how alcohols and alkyl sulfonates behave in substitution and elimination reactions

213) Which reagents are appropriate to carry out the conversion shown?

A) HBr followed by NaI

B) NaH followed by CH3CH2

C) HCl followed by CH3CH2MgBr

D) TsCl/pyridine followed by NaCl

E) NaOH followed by NaSH

Diff: 3

Learning Objective: 7.10 Determine how alcohols and alkyl sulfonates behave in substitution and elimination reactions

214) Which reagents are appropriate to carry out the conversion shown?

A) conc. H2SO4 followed by CH3NH2

B) NaH followed by CH3CH2

C) NaOH followed by CH3NH2

D) TsCl/pyridine followed by NaCl

E) NaBr followed by CH3NH2

Diff: 3

Learning Objective: 7.10 Determine how alcohols and alkyl sulfonates behave in substitution and elimination reactions

215) Which reagents are appropriate to carry out the conversion shown?

A) 1. conc. H2SO4; 2.

B) 1. HBr; 2.

C) 1. NaOH; 2.

D) 1. TsCl/pyridine; 2.CH3CH2COH

E) 1. TsCl/pyridine; 2.

Diff: 3

Learning Objective: 7.10 Determine how alcohols and alkyl sulfonates behave in substitution and elimination reactions

216) Which reagents are appropriate to carry out the conversion shown?

A) H2S in water

B) H2S in DMSO

C) NaSH in water

D) NaSH in DMSO

Diff: 1

Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product

217) Which reagents are appropriate to carry out the conversion shown?

A) HN3 in water

B) HN3 in acetonitrile

C) NaN3 in water

D) NaN3 in acetonitrile

Diff: 1

Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product

218) Which reagents are appropriate to carry out the conversion shown?

A) NaOH in water

B) NaOH in ether

C) H2O

D) CH3OH

Diff: 2

Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product

219) Which reagents are appropriate to carry out the conversion shown?

A) CH3CH2OH

B) CH3CH2COOH

C) NaOH followed by CH3CH2OH

D) t-BuOK

E) NaOH followed by CH3CH2MgBr

Diff: 2

Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product

220) How could you change the reaction conditions given to most strongly favor an E2 mechanism?

A) Use a higher concentration of water

B) Use a stronger base

C) Add a stronger nucleophile

D) Use a tertiary alkyl halide

E) Increase the concentration of the reactant

Diff: 1

Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product

221) How could you change the reaction conditions given to most strongly favor an E1 mechanism?

A) Use a higher concentration of water

B) Use a weaker base

C) Use a stronger nucleophile

D) Use a primary alkyl halide

E) Increase the concentration of the reactant

Diff: 2

Learning Objective: 7.11 Perform a retrosynthetic analysis to find the synthetic strategy that will produce the target product

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