Addition Reactions Of Alkenes Full Test Bank Chapter 8

Organic Chemistry, 4e (Klein)

Chapter 8 Addition Reactions of Alkenes

1) In an addition reaction to an alkene, the π bond is ________.

A) a nucleophile

B) an electrophile

C) a leaving group

D) A and B

E) B and C

Diff: 1

Learning Objective: 8.1 Define an addition reaction, name five kinds of addition reactions, and list the groups added in each kind of reaction

2) Addition reactions of alkenes are characterized by ________.

A) formation of a π bond

B) addition of two groups across a double bond

C) breaking of a π bond

D) A and B

E) B and C

Diff: 2

Learning Objective: 8.1 Define an addition reaction, name five kinds of addition reactions, and list the groups added in each kind of reaction

3) Alkenes are found in ________, which are used by living organisms to trigger specific behavioral responses in other members of the same species.

A) polymers

B) olefins

C) hormones

D) pheromones

E) monomers

Diff: 1

Learning Objective: 8.2 Provide examples of alkenes in both nature and industry

4) What is a compound that does not have a double bond?

A) allicin (garlic)

B) geraniol (roses)

C) cholesterol

D) limonene (oranges)

E) ammonia

Diff: 1

Learning Objective: 8.2 Provide examples of alkenes in both nature and industry

5) Identify the compound that is not produced industrially from an alkene.

A) acetic acid

B) methanol

C) isopropyl alcohol

D) acetone

E) ethylene glycol

Diff: 1

Learning Objective: 8.2 Provide examples of alkenes in both nature and industry

6) The alkene precursor to the industrial production of ethanol is ________.

A) ethane

B) ethene

C) ozonolysis

D) propylene

E) acetic acid

Diff: 1

Learning Objective: 8.2 Provide examples of alkenes in both nature and industry

7) The alkene precursor to the industrial production of acetone is ________.

A) isopropyl alcohol

B) propane

C) dihydroxylation

D) ethylene

E) propene

Diff: 1

Learning Objective: 8.2 Provide examples of alkenes in both nature and industry

8) Most π bonds are quite prone to reaction with a(n) ________, also referred to as electron-seeking reagents.

A) alcohol

B) nucleophile

C) solvent

D) electrophile

E) leaving group

Diff: 1

Learning Objective: 8.4 Describe the role of temperature in determining whether an addition or elimination reaction will occur and whether the reactants or products will be favored

9) The decrease in entropy (the ΔS value is negative) observed for alkene addition reactions results from ________.

A) the breaking of a π and σ bond.

B) the formation of two σ bonds.

C) the reaction being exothermic.

D) two molecules reacting to form a single molecule.

E) the temperature dependence of the ΔS term.

Diff: 1

Learning Objective: 8.4 Describe the role of temperature in determining whether an addition or elimination reaction will occur and whether the reactants or products will be favored

10) Which statement best describes the temperature dependence of an addition reaction?

A) Addition reactions are thermodynamically favored at all temperatures.

B) Addition reactions are thermodynamically disfavored at all temperatures.

C) Addition reactions are thermodynamically favored at low temperatures.

D) Addition reactions are thermodynamically favored at high temperatures.

E) Addition reactions are thermodynamically impossible.

Diff: 1

Learning Objective: 8.4 Describe the role of temperature in determining whether an addition or elimination reaction will occur and whether the reactants or products will be favored

11) For an addition reaction, why does free energy, ΔG, become more positive with increasing temperature?

A) The positive entropy dominates at high temperature.

B) The negative entropy dominates at high temperature.

C) The positive enthalpy dominates at high temperature.

D) The negative enthalpy dominates at high temperature.

E) The enthalpy and entropy cancel at high temperature.

Diff: 2

Learning Objective: 8.4 Describe the role of temperature in determining whether an addition or elimination reaction will occur and whether the reactants or products will be favored

12) For this question, the "entropy term" refers to "-TΔS". Addition reactions are generally favorable at low temperatures because ________.

A) the positive enthalpy term is larger than the negative entropy term

B) the negative enthalpy term is larger than the positive entropy term

C) the positive enthalpy term is smaller than the negative entropy term

D) the negative enthalpy term is smaller than the positive entropy term

E) the enthalpy and entropy terms are equal

Diff: 3

Learning Objective: 8.4 Describe the role of temperature in determining whether an addition or elimination reaction will occur and whether the reactants or products will be favored

13) The regioselectivity and stereospecificity in the hydrohalogenation of an alkene is best described as ________.

A) Markovnikov orientation with syn-addition

B) Markovnikov orientation with anti-addition

C) anti-Markovnikov orientation with syn-addition

D) anti-Markovnikov orientation with anti-addition

E) Markovnikov orientation with both syn- and anti-addition

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

14) In the addition reaction of HI to 2-methyl-2-butene, what is the first step?

A) attack of 2-methyl-2-butene initiated by an iodide ion

B) attack of 2-methyl-2-butene initiated by an iodine atom

C) isomerization of 2-iodo-2-methylbutene

D) formation of a carbocation at carbon two (C-2)

E) formation of carbocation at carbon three (C-3)

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

15) Which of the structures shown depicts the most likely carbocation intermediate formed in the hydrohalogenation reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

16) What is the expected product for the hydrohalogenation of the following alkene with HBr?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

17) What is the expected Markovnikov addition product from the addition of HI to 2-methyl-2-butene?

A) 2-iodopentane

B) 2-iodo-2-methylbutane

C) 1-iodo-2-methylbutane

D) 1-iodo-3-methylbutane

E) 2-iodo-3-methylbutane

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

18) What is the expected product when the given alkene undergoes Markovnikov hydrohalogenation with HBr?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

19) What is the expected major product of the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

20) What is the expected major product of the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

21) What is the expected major product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

22) Which of the molecules below arises when the given alkene undergoes anti-Markovnikov hydrohalogenation with HBr?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

23) Which of the alkenes shown below would produce a chiral center upon Markovnikov hydrohalogenation?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

24) Predict the major product(s) for the following reaction:

A) I

B) II

C) III

D) II & III

E) IV

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

25) Which of the alkenes below would be expected to produce at least one chiral center upon hydrohalogenation in the presence of peroxide?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

26) Which of the given reaction schemes would produce the molecule shown below as the major product?

A) I

B) II

C) III

D) Both I and II

E) Both II and III

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

27) Which of the molecules below are enantiomers formed as products upon reaction of HBr with 4-methylpent-1-ene?

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

28) Which of the following carbocations is (are) likely to undergo rearrangement through a methide shift?

A) I

B) II

C) III

D) I and II

E) I, II and III

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

29) Which of the following carbocations is (are) likely to undergo rearrangement through a hydride shift?

A) I

B) II

C) III

D) I and II

E) I and III

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

30) Predict the expected major product(s) of HCl addition to the alkene below?

A) I and II

B) II and III

C) III and IV

D) II and IV

E) V

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

31) Predict the expected major product(s) of HBr addition to the alkene shown below?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

32) Predict the expected major product of the reaction below?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

33) What is the IUPAC name of the expected major product of the following reaction?

A) 1-chloro-2-methylbutane

B) 1-chloro-3-methylbutane

C) 2-chloro-2-methylbutane

D) 2-chloro-3-methylbutane

E) 1-chloropentane

Diff: 3

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

34) Select the expected major product(s) of the following reaction.

A) I

B) II

C) III

D) I and II

E) I and III

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

35) Provide an IUPAC name for the following compound.

A) isohexene

B) 2-methyl-5-hexene

C) 5-methyl-2-hexene

D) 5-methyl-1-hexene

E) 2-methyl-6-hexene

Diff: 1

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

36) Select the expected major product(s) of the following reaction.

A) I

B) II

C) III

D) I and II

E) I, II and III

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

37) Identify the expected major organic product of the following reaction:

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

38) The product shown in the box can be produced by treatment of each of the alkenes shown with HCl. Which reaction intermediate would explain this observation?

A) I

B) II

C) III

D) IV

E) None of the above

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

39) When the two constitutional isomers shown below are reacted with HCl, the same major product is formed. Identify the structure of this major product.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

40) Addition of HI to the alkene given below, results in a significant yield of the product shown. What other product(s) might also be obtained?

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 3

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

41) The regioselectivity and stereospecificity in the acid-catalyzed hydration of an alkene is best described as

A) Markovnikov orientation with syn-addition.

B) Markovnikov orientation with anti-addition.

C) anti-Markovnikov orientation with syn-addition.

D) anti-Markovnikov orientation with anti-addition.

E) Markovnikov orientation with both syn- and anti-addition.

Diff: 1

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

42) Predict the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

43) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

44) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

45) Identify the expected major product of the following reaction.

A) I and III

B) II

C) II and III

D) IV

E) III and V

Diff: 2

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

46) What is the expected major product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

47) Identify the compound that would react most slowly with a dilute aqueous solution of H2SO4.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

48) The three compounds below can form a carbocation under aqueous acidic conditions. Which will form the same carbocation?

A) II only

B) I and II

C) I and III

D) II and III

E) All three will form the same carbocation

Diff: 2

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

49) What would be the optimal conditions to achieve the following synthesis?

A) dilute H2SO4

B) concentrated H2SO4

C) dilute HBr

D) concentrated HBr

E) aqueous NaOH

Diff: 2

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

50) What would be the optimal conditions to achieve the following synthesis?

A) dilute aqueous H2SO4

B) concentrated H2SO4

C) dilute aqueous HBr

D) concentrated HBr

E) aqueous NaOH

Diff: 2

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

51) Which of the following is the major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

52) Describe the product(s) of the reaction below.

A) only one stereoisomer

B) an equal mixture of enantiomers

C) a mixture of diastereomers and their enantiomers

D) a mixture of constitutional isomers

E) a mixture of constitutional isomers and their enantiomers

Diff: 3

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

53) Identify the expected major organic product(s) for the following reaction.

A) I

B) II

C) III

D) I and II

E) I and III

Diff: 1

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

54) For the following reaction provide the expected major organic product(s). Include all stereoisomers and clearly show relevant stereochemistry.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 1

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

55) Identify the expected major organic product(s) of the following reaction.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 2

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

56) The reaction shown below generates an achiral product from a chiral starting material. Identify the intermediate that would explain the production of an achiral product.

A) I

B) II

C) III

D) II and V

E) V

Diff: 2

Learning Objective: 8.6 Describe an acid-catalyzed hydration reaction including reactants, intermediates, products, regiochemistry, and stereochemistry

57) The regioselectivity and stereospecificity in the reaction of an alkene with Hg(OAc)2 and water (the oxymercuration of an alkene) is best described as

A) Markovnikov orientation with syn-addition.

B) Markovnikov orientation with anti-addition.

C) anti-Markovnikov orientation with syn-addition.

D) anti-Markovnikov orientation with anti-addition.

E) Markovnikov orientation with both syn- and anti-addition.

Diff: 1

Learning Objective: 8.7 Discuss hydration of an alkene by oxymercuration-demercuration, explaining why there is no carbocation rearrangement

58) What molecular transformation is achieved by subjecting an alkene to an oxymercuration-demercuration reaction sequence?

A) Markovnikov addition of H2O, promoting rearrangement

B) Markovnikov addition of H2O, preventing rearrangement

C) anti-Markovnikov addition of H2O, promoting rearrangement

D) anti-Markovnikov addition of H2O, preventing rearrangement

E) anti-Markovnikov addition of H2O, syn-hydroxylation

Diff: 1

Learning Objective: 8.7 Discuss hydration of an alkene by oxymercuration-demercuration, explaining why there is no carbocation rearrangement

59) What is the expected major product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.7 Discuss hydration of an alkene by oxymercuration-demercuration, explaining why there is no carbocation rearrangement

60) What is the expected major product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.7 Discuss hydration of an alkene by oxymercuration-demercuration, explaining why there is no carbocation rearrangement

61) What is the expected major product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.7 Discuss hydration of an alkene by oxymercuration-demercuration, explaining why there is no carbocation rearrangement

62) Identify the expected major product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.7 Discuss hydration of an alkene by oxymercuration-demercuration, explaining why there is no carbocation rearrangement

63) When an alkene is treated with Hg(OAc)2 in EtOH, followed by reaction with basic NaBH4, what functional group is formed?

A) ether

B) epoxide

C) alkane

D) syn diol

E) alkyne

Diff: 2

Learning Objective: 8.7 Discuss hydration of an alkene by oxymercuration-demercuration, explaining why there is no carbocation rearrangement

64) When a terminal alkene undergoes hydroboration-oxidation, two constitutional isomers are possible, but only one isomer is observed as the major product. Such reactions are described as ________.

A) stereospecific

B) regiospecific

C) stereoselective

D) regioselective

E) constitutionally constrained

Diff: 1

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

65) The mechanism of hydroboration-oxidation must explain the observed ________ addition of the H and OH to the alkene as well as the ________ regiochemistry.

A) syn, Markovnikov

B) anti, anti-Markovnikov

C) syn, anti-Markovnikov

D) anti, Markovnikov

E) stepwise, mixed

Diff: 1

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

66) The regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene is best described as ________.

A) Markovnikov orientation with syn-addition

B) Markovnikov orientation with anti-addition

C) Anti-Markovnikov orientation with syn-addition

D) Anti-Markovnikov orientation with anti-addition

E) Markovnikov orientation with both syn- and anti-addition

Diff: 1

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

67) What reagent(s) would accomplish the following synthesis?

A) H2O/H+

B) H2O/ROOR

C) NaOH, H2O

D) 1. Hg(OAc)2, H2O; 2) NaBH4

E) 1. BH3•THF; 2. NaOH, H2O2, H2O

Diff: 1

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

68) Identify the expected major product(s) for the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

69) Identify the expected major product(s) for the following reaction sequence.

A) I

B) II

C) III

D) I and II

E) I and III

Diff: 2

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

70) What is the expected major product for the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

71) What is the expected major product for the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

72) What is the expected major product for the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

73) Identify the expected major organic product(s) for the following reaction sequence.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 1

Learning Objective: 8.8 Discuss the anti-Markovnikov addition of water across an alkene by hydroboration-oxidation

74) Identify the product from the hydrogenation of an alkene.

A) dihaloalkane

B) alkane

C) haloalkane

D) alcohol

E) ether

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

75) Identify the major organic product for the reaction shown below.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

76) Provide the name of the product formed from the following reaction:

A) 1-chloro-2-methylcyclohexane

B) 1-chloro-3-methylcyclohexane

C) 1-chloro-4-methylcyclohexane

D) 1-chloro-5-methylcyclohexane

E) 5-chloro-1-methylcyclohexane

Diff: 2

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

77) Provide the name of the product formed from the following reaction:

A) No reaction

B) cis-1,2-dimethylcyclohexene

C) trans-3,4-dimethylcyclohexane

D) trans-1,2-dimethylcyclohexene

E) cis-3,4-dimethylcyclohexane

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

78) Which of the following sets of reagents accomplishes the transformation shown below?

A) H2/HCl

B) H2/H2SO4

C) H2/Pd

D) H2O/Pd

E) H2O/H2SO4

Diff: 2

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

79) Which of the reagents below would convert cyclopentene into cyclopentane?

A) H2 and Pt

B) dilute H2SO4

C) Heat

D) conc. H2SO4

E) Br2

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

80) Which alkene would yield 3-methylpentane when subjected to catalytic hydrogenation?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

81) How many moles of hydrogen gas (H2) are consumed in the catalytic reduction of 1 mole of the following compound?

A) 0.5

B) 1

C) 2

D) 3

E) 4

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

82) How many moles of hydrogen gas (H2) are required to completely reduce 1 mole of the following compound?

A) 0.5

B) 1

C) 2

D) 3

E) 4

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

83) Which of the catalysts listed are used in the homogenous catalytic hydrogenation of alkenes?

I. Ni II. Pt III. Wilkinson's catalyst IV. Pd

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

84) In conducting the catalytic hydrogenation of an alkene, which catalyst listed is most likely to be soluble in the organic solvent?

A) Ni

B) Pt

C) Pd

D) Wilkinson's catalyst

E) All of the above are soluble

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

85) Wilkinson's catalyst accomplishes which of the listed molecular transformations?

A) syn addition of H2 to an alkene

B) anti addition of H2 to an alkene

C) syn dihydroxylation of an alkene

D) anti dihydroxylation of an alkene

E) oxidative cleavage of an alkene

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

86) Identify Wilkinson's catalyst.

A) (Ph3P)3RhCl

B) (Ph3P)3RhBr

C) (Ph3P)3PbCl

D) (Ph3P)3PbBr

E) (Ph3P)3RuCl

Diff: 1

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

87) Which of the following will yield 2-methylpentane upon catalytic hydrogenation?

A) 2-methyl-1-pentene

B) 2-methyl-2-pentene

C) 4-methyl-2-pentene

D) 4-methyl-1-pentene

E) All of the above

Diff: 2

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

88) How many moles of hydrogen gas (H2) are required to completely reduce 1 mole of the following compound?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

89) Identify the major organic product(s) generated from the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.9 Explain why catalytic hydrogenation proceeds via syn addition

90) Which reaction intermediate is formed when 4methylcyclohexene reacts with Br2 dissolved in CCl4?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

91) What is the expected major product upon completion of the following?

A) 1-chloropentane

B) 2-chloropentane

C) 1,1-dichloropentane

D) 2,2-dichloropentane

E) 1,2-dichloropentane

Diff: 1

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

92) Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following as the major product?

A) 2,3-dibromo-2-methylpentane

B) 2,2-dibromo-3-methylpentane

C) 3,3-dibromo-2-methylpentane

D) 2-bromo-2-methylpentane

E) 3-bromo-2-methylpentane

Diff: 1

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

93) Which of the statements describes the products expected from the halogenation reaction shown below?

A) Equal amounts of I and II are produced.

B) Equal amounts of III and IV are produced.

C) Equal amounts of I and III are produced.

D) Equal amounts of II and III are produced.

E) A mixture of I, II and III are produced.

Diff: 3

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

94) Identify the first reaction intermediate expected during the reaction of an alkene with Br2 and H2O.

A) a bromonium ion

B) the most stable carbocation with OH on the adjacent carbon

C) the most stable carbocation with Br on the adjacent carbon

D) a cyclic oxonium ion

E) the most stable carbanion

Diff: 1

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

95) What is the expected major product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

96) What is the expected major product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

97) Identify the expected major product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

98) The reaction following reaction is expected to produce which of the following as the major product?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

99) Identify the expected major organic product from the reaction shown below.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

100) Identify the intermediate that would give rise to the product shown in the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

101) Predict the product(s) for the following reaction.

A) I and II

B) II and III

C) III and IV

D) I and III

E) V only

Diff: 2

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

102) Identify the Fischer projection(s) of the expected major product(s) for the following reaction.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 3

Learning Objective: 8.10 Describe a halogenation reaction, including reactants, intermediates, products, and stereochemistry

103) Identify the expected major products for the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.11 Describe the process for anti dihydroxylation

104) Identify the expected major product(s) for the following reaction.

A) I

B) II

C) III

D) I and III

E) I, II and III

Diff: 2

Learning Objective: 8.11 Describe the process for anti dihydroxylation

105) What are the expected major products for the following reaction sequence?

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 2

Learning Objective: 8.11 Describe the process for anti dihydroxylation

106) Which of the following is the IUPAC name for the compound shown below?

A) 2-ethyl-1,1,3-trimethylbutene

B) 3-ethyl-2,4-dimethyl-2-pentene

C) 2,4-dimethylhexene

D) 4-ethyl-1,3-dimethyl-3-pentene

E) 3-isopropyl-2-methyl-2-pentene

Diff: 1

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

107) Identify the expected products for the following dihydroxylation reaction.

A) Equal amounts of I and II

B) Equal amounts of III and IV

C) Equal amounts of I and IV

D) Equal amounts of II and III

E) Equal amounts of I and III

Diff: 3

Learning Objective: 8.11 Describe the process for anti dihydroxylation

108) An unknown alkene was reacted with MCPBA in dichloromethane, followed by reaction with H2O/H+. A racemic mixture of the compound shown below was obtained. What is the IUPAC name of the starting alkene?

A) (Z)-3-methylpent-2-ene

B) (E)-3-methylpent-2-ene

C) 2-methylpent-2-ene

D) 2,3-dimethylbut-2-ene

E) 1,2-diemthylbut-2-ene

Diff: 3

Learning Objective: 8.11 Describe the process for anti dihydroxylation

109) Identify the Fischer projection(s) of the major product(s) of the following reaction sequence.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 3

Learning Objective: 8.11 Describe the process for anti dihydroxylation

110) Identify the expected major organic product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.12 Describe a syn dihydroxylation reaction

111) Treatment of 1,2-dimethylcyclopentene with OsO4 with NMO produces which of the following?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.12 Describe a syn dihydroxylation reaction

112) Identify the expected major organic product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.12 Describe a syn dihydroxylation reaction

113) Which of the following alkene addition reactions occur specifically in syn fashion?

A) dihydroxylation using catalytic OsO4, NMO

B) halohydrin formation with Br2

C) halogenation with Cl2

D) hydrohalogenation with HCl

E) oxymercuration-demercuration

Diff: 1

Learning Objective: 8.12 Describe a syn dihydroxylation reaction

114) What is the expected major product for the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.12 Describe a syn dihydroxylation reaction

115) Provide the expected major organic product(s) of the reaction sequence shown.

A) I only

B) II only

C) III only

D) III and V

E) IV and V

Diff: 1

Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis

116) Which of the following reagents effectively cleaves both the sigma and pi bonds of an alkene?

A) Cl2

B) RCO3H

C) H2SO4

D) cold KMnO4, NaOH

E) 1. O3; 2. DMS

Diff: 1

Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis

117) How many carbonyl groups (C=O) are generated upon treatment of the molecule below with ozone, followed by DMS?

A) 0

B) 2

C) 3

D) 4

E) 8

Diff: 2

Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis

118) Which of the following alkenes is needed to synthesize the product in the reaction shown below?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis

119) What is the expected major product of the reaction sequence shown below?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis

120) What are the expected major products for the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis

121) Identify the expected major organic products generated in the reaction sequence shown below.

A) I and II

B) II and III

C) III and IV

D) IV and V

E) III and V

Diff: 2

Learning Objective: 8.13 Describe the formation of carbonyl groups by ozonolysis

122) Which of the following alkene addition reactions occur specifically with an anti orientation?

A) hydroboration-oxidation

B) addition of Br2

C) addition of H2

D) addition of H2O in dilute acid

E) oxymercuration-demercuration

Diff: 1

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

123) The Markovnikov product resulting from an addition reaction to a trisubstituted alkene is formed because ________.

A) the product is statistically favored

B) steric hindrance favors its formation

C) the reaction proceeds via the more stable carbocation

D) the reaction forms the more stable product

E) All of the above are valid reasons

Diff: 1

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

124) What is the expected major product for the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

125) Which reagents are most likely to accomplish the reaction shown below?

A) 1. BH3∙THF; 2. H2O2, NaOH

B) H+, H2O

C) 1. Hg(OAc)2, H2O; 2. NaBH4

D) H2O, ROOR

E) NaOH, H2O

Diff: 1

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

126) Which reaction is not stereospecific?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

127) Identify the expected major product(s) of the following reaction.

A) a meso dibromide

B) a mixture of optically active enantiomeric dibromides

C) a mixture of diasteromeric isomers

D) (Z)-3,4-dibromo-3-hexene

E) (E)-3,4-dibromo-3-hexene

Diff: 3

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

128) Which of the following alkenes will yield a meso dihalide when reacted with Br2/CCl4 at room temperature?

A) I

B) II

C) III

D) IV

E) Both II and IV

Diff: 3

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

129) What is the expected major product resulting from the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

130) What are the expected major products resulting from the following reaction?

A) I

B) II

C) III

D) IV

E) All of the above are produced in equal amounts

Diff: 2

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

131) Identify the Fischer projection(s) of the major product(s) for the following reaction.

A) I and II

B) II and II

C) III and IV

D) I and III

E) II and IV

Diff: 2

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

132) Identify the Fischer projection(s) of the major product(s) for the following reaction.

A) I and II

B) II and II

C) III and IV

D) I and III

E) II and IV

Diff: 2

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

133) Identify the product of the following reaction that illustrates the correct regiochemical and stereochemical transformation.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

134) Identify the best reagents to accomplish a Markovnikov addition of water to an unsymmetrical alkene while preventing carbocation rearrangement.

A) water and dilute acid

B) water and concentrated acid

C) 1. Hg(OAc)2, H2O; 2. NaBH4, NaOH

D) 1. BH3•THF; 2. H2O2, NaOH

E) 1. OsO4; 2. NaHSO3, H2O

Diff: 2

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

135) For the reaction sequence shown, what is the expected major product?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

136) What is the expected major product of the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

137) What is the expected major product of the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

138) Which is the correct sequence of steps necessary to complete the following transformation?

A) I then II then III

B) II then I then III

C) II then IV

D) III then I

E) I then IV then II then III

Diff: 3

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

139) What is the expected major product of the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

140) Predict the expected major product of the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

141) Predict the expected major products of the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

142) Predict the expected major product(s) of the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

143) What is the expected major product of the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

144) Identify the major product(s) for the following reaction sequence.

A) I

B) I & II

C) III

D) III & IV

E) V

Diff: 3

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

145) What is the expected major product of the following reaction sequence?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

146) For the following reaction sequence, identify the expected major organic products and provide their stereochemical relationship.

A) I and II; enantiomers

B) III and IV; enantiomers

C) I and II; diastereomers

D) II and III; diastereomers

E) I and IV; enantiomers

Diff: 3

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

147) Identify the structure of (E)-4,5-dimethylhept-3-ene.

A)

B)

C)

D)

E)

Diff: 2

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

148) Identify the IUPAC name for the following compound.

A) 1-methyl-2-cyclohexene

B) 2-methylcyclohexene

C) 3-methylcyclohexene

D) 1-methyl-5-cyclohexene

E) 6-methyl-cyclohexene

Diff: 1

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

149) Which of the following is the correct structure of 4-methylcyclopentene?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

150) Unknown compound A has the molecular formula C8H14. Subjecting compound A to ozonolysis produces the compound shown below as the major organic product. Identify the correct structure of compound A from the following choices.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

151) Which of the following is the correct structure of 2-methyl-1-butene?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

152) Identify the geometry of each alkene as E, Z, or neither (non-stereoisomeric).

A) I is neither; II is E

B) I is neither; II is Z

C) I is Z; II is neither

D) I is Z; II is E

E) I is E; II is Z

Diff: 1

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

153) Identify the geometry of each alkene as E, Z, or neither (non-stereoisomeric).

A) I is neither; II is Z

B) I is E; II is E

C) I is Z; II is Z

D) I is Z; II is E

E) I is E; II is Z

Diff: 1

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

154) Identify the geometry of each alkene as E, Z, or neither (non-stereoisomeric).

A) I is neither; II is E

B) I is E; II is E

C) I is Z; II is Z

D) I is Z; II is E

E) I is E; II is Z

Diff: 2

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

155) Identify the geometry of each alkene as E, Z, or neither (non-stereoisomeric).

A) I is neither; II is E

B) I is E; II is E

C) I is Z; II is Z

D) I is Z; II is E

E) I is E; II is Z

Diff: 2

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

156) Provide an IUPAC name for the following compound.

A) (Z)-4-cyclopentyl-2-pentene

B) (E)-4-cyclopentyl-4-methyl-2-butene

C) (Z)-4-cyclopentyl-4-methyl-2-butene

D) (E)-4-cyclopentyl-2-pentene

E) (Z)-2-cyclopentyl-3-pentene

Diff: 1

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

157) Identify the E isomer of 2-methyl-3-heptene.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

158) Identify the E isomer of 3,4-dimethyl-3-heptene.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.3 Assign an IUPAC (systematic) name to alkenes

159) Which of the following alkene addition reactions occur stereospecifically in anti fashion?

A) dihydroxylation using catalytic OsO4, NMO

B) catalytic hydrogenation of H2

C) hydroboration-oxidation

D) halohydrin formation with Br2 and H2O

E) oxymercuration-demercuration

Diff: 1

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

160) Which of the following alkene addition reactions occur stereospecifically in syn fashion?

A) dihalogenation with Br2

B) halohydrin formation with Br2 and H2O

C) acid catalyzed hydration

D) catalytic hydrogenation of H2

E) oxymercuration-demurcuration

Diff: 1

Learning Objective: 8.14 List three factors that must be considered in predicting the products of an addition reaction

161) Which is the correct sequence of steps necessary to complete the following reaction?

A) I then II then III

B) II then I then III

C) II then IV

D) III then I

E) III then IV

Diff: 2

Learning Objective: 8.15 Describe mechanisms for changing the positions of a leaving group or a pi bond

162) Which of the following starting molecules would not give rise to the major product shown in the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 8.5 Define hydrohalogenation, describing the reaction in terms of its regiochemistry and the effects of peroxides

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