Essential Organic Chemistry 3rd Edition By Paula Yurkanis Bruice – Test Bank

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Sample Questions Posted Below

 

Essential Organic Chemistry, 3e, (Bruice)

Chapter 5   Alkenes ∙ Thermodynamics and Kinetics

1) Give the general formula for a cyclic alkene.

A) CnH2n-4

B) CnH2n-2

C) CnH2n

D) CnH2n+2

E) CnH2n+4

Answer:  B

Diff: 1

Section:  5-1

Objective:  G2, G3

LO:  5.1

2) Give the possibilities in structure for a compound with a formula of C6H10.

A) no rings, no double bonds, no triple bonds

B) one double bond, or one ring

C) two rings, two double bonds, one double bond + one ring, or one triple bond

D) three rings, three double bonds, two double bonds + one ring, one ring + two double bonds, one triple bond + one ring, or one double bond + one ring

E) benzene

Answer:  C

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

3) Benzene is a molecule with formula C6H6. If it contains no triple bonds, then how many total double bonds and rings does it contain?

A) 1

B) 2

C) 3

D) 4

E) 5

Answer:  D

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

4) β-Phellandrene is a hydrocarbon component of eucalyptus oil whose molecular formula is C10H16. A molecule of β-phellandrene contains 2 π-bonds. How many rings are in β-phellandrene?

A) 0

B) 1

C) 2

D) 3

E) 4

Answer:  B

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

5) An acyclic hydrocarbon with the formula C20H34 has how many pi bonds? 

A) 2

B) 3

C) 4

D) 5

E) 6

Answer:  C

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

6) Name the structure.

A) 2-ethyl-1-pentene

B) 2-propyl-1-butene

C) 3-methylenehexane

D) 3-methyl-3-hexene

E) ethyl propyl ethene

Answer:  A

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

7) Name the structure.

A) 2-methyl-2,4-pentadiene

B) 4-methyl-1,4-pentadiene

C) 2-methylene-4-pentene

D) 4-methylene-2-pentene

E) 2-methyl-1,4-pentadiene

Answer:  E

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

8) Name the structure.

A) 7-chloro-3-ethyl-4-methyl-3-heptene

B) 1-chloro-5-ethyl-4-methyl-3-heptene

C) 1-chloro-3-pentenyl-2-pentene

D) cis-7-chloro-3-ethyl-4-methyl-3-heptene

E) trans-7-chloro-3-ethyl-4-methyl-3-heptene

Answer:  A

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

9) Name the structure.

A) 4-chlorocyclohexene

B) 1-chloro-3-cyclohexene

C) 1-chloro-3-cycloheptene

D) 4-chlorocycloheptane

E) 4-chlorocycloheptene

Answer:  E

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

10) Name the structure.

H2CCHCH2I

A) vinyl iodide

B) allyl iodide

C) 1-iodo-2-propene

D) iodomethylethene

E) 2-iodo-1-propene

Answer:  B

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

11) What is the common name for the following compound?

A) t-butylene

B) sec-butylene

C) isobutylene

D) butylene

E) methylpropylene

Answer:  C

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

12) What is the IUPAC name for the following compound?

 

A) 2-methyl-1-butene

B) isopentene

C) 2-methybutene

D) 2-ethylpropene

E) 3-methyl-3-butene

Answer:  A

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

13) What is the IUPAC name for the following compound?

 

A) 5-methylcyclohexene

B) 4-methylcyclohexene

C) 1-methyl-3-cyclohexene

D) 1-methyl-4-cyclohexene

E) methylcyclohexene

Answer:  B

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

14) Which of the following is vinyl chloride?

A) CH3CH2Cl

B) CH2CHCH2Cl

C) CH2CHCl

D) 

E) 

Answer:  C

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

15) Which of the following is an allylic alcohol?

A) CH2CHCH2OCH3

B) CH2CHCH2CH3

C) HOCHCHCH2CH3

D) CH3CHCHCH2OH

E) CH2CHCH2CH2OH

Answer:  D

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

16) Which of the following statements about ethene, C2H4, is incorrect?

A) The H-C-H bond angles are approximately 109.5°.

B) All of the hydrogen atoms are in the same plane.

C) There is a total of five sigma bonds.

D) The carbon atoms are sp2 hybridized.

E) The H-C-H bond angles are approximately 120°.

Answer:  A

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

17) Which of the following statements about propene, CH3CHCH2, is correct?

A) All nine atoms lie in the same plane.

B) The compound has a cis and trans isomer.

C) It generally acts as a Lewis acid.

D) There is a total of eight sigma bonds.

E) All the carbon atoms are sp2 hybridized.

Answer:  D

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

18) Name the structure.

A) cis-3-ethyl-4-hydroxymethyl-hex-3-en-1-yne

B) cis-2,3-diethylpent-2-en-4-yn-1-ol

C) trans-2,3-diethylpent-2-en-4-yn-1-ol

D) cis-3,4-diethylpent-3-en-1-yn-5-ol

E) trans-3,4-diethylpent-3-en-1-yn-5-ol

Answer:  C

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

19) How many carbons are in the planar double-bond system of 3-methylcyclopentene?

A) 0

B) 1

C) 2

D) 3

E) 4

Answer:  E

Diff: 1

Section:  5-1

Objective:  G2, G3

LO:  5.1

20) Name the structure.

A) cis-4,5-dimethyl-4-hepten-1-ol

B) trans-3,4-dimethyl-3-hepten-7-ol

C) cis-3,4-dimethyl-3-hepten-7-ol

D) trans-4,5-dimethyl-4-hepten-1-ol

E) trans-4,5-dimethyl-4-heptenol

Answer:  D

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

21) Name the structure.

A) (Z)-4,5-dimethyl-4-hepten-1-ol

B) (E)-4,5-dimethyl-4-hepten-1-ol

C) (E)-3,4-dimethyl-3-hepten-7-ol

D) (Z)-3,4-dimethyl-3-hepten-7-ol

E) (E)-4,5-dimethyl-4-heptenol

Answer:  B

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

22) Name the structure.

A) (Z)-3-ethyl-2-hydroxymethyl-2-penten-4-ynal

B) (E)-3-ethyl-2-hydroxymethyl-2-penten-4-ynal

C) (Z)-3-ethyl-5-hydroxymethyl-3-penten-1-ynal

D) (E)-3-ethyl-5-hydroxymethyl-3-penten-1-ynal

E) 3-ethyl-5-hydroxymethyl-3-penten-1-ynal

Answer:  A

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

23) Name the structure.

A) (2E,4E)-7-chloro-2,4-heptadiene

B) (2Z,4E)-7-chloro-2,4-heptadiene

C) (2Z,4Z)-7-chloro-2,4-heptadiene

D) (2E,4Z)-7-chloro-2,4-heptadiene

E) 7-chloro-2,4-heptadiene

Answer:  D

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

24) Which of the following is capable of exhibiting cis-trans isomerism?

A) 1-butene

B) 1-pentene

C) cyclohexene

D) ethene

E) 2-butene

Answer:  E

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

25) Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below?

A) E

B) Z

C) neither E nor Z

Answer:  C

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

26) Which of the following is not an electrophile?

A) H+

B) BF3

C) +NO2

D) Fe+3

E) CH2CH2

Answer:  E

Diff: 1

Section:  5-3

Objective:  G2, G3

LO:  5.3

27) Which of the following is not a nucleophile?

A) FeBr3

B) Br-

C) NH3

D)  

E) CH3OCH3

Answer:  A

Diff: 1

Section:  5-3

Objective:  G2, G3

LO:  5.3

28) How many transition states are present in the following reaction diagram?

A) 3

B) 4

C) 5

D) 2

E) 1

Answer:  D

Diff: 1

Section:  5-3

Objective:  G2, G3

LO:  5.3

29) Which set of curved arrows correctly shows the flow of electrons in this reaction?

A) 

B) 

C) 

D) 

Answer:  A

Diff: 2

Section:  5-3

Objective:  G2, G3

LO:  5.4

30) Select all of the curved arrows that are correct for this reaction.

A) A

B) B

C) C

D) D

Answer:  B, C

Diff: 3

Section:  5-3

Objective:  G2, G3

LO:  5.4

31) Select all of the curved arrows that are correct for this reaction.

A) A

B) B

C) C

D) D

Answer:  B, C, D

Diff: 3

Section:  5-3

Objective:  G2, G3

LO:  5.4

32) Select all of the curved arrows that are correct for this reaction.

A) A

B) B

C) C

D) D

Answer:  B, C

Diff: 3

Section:  5-3

Objective:  G2, G3

LO:  5.4

33) Select all of the curved arrows that are correct for this reaction.

A) A

B) B

C) C

D) D

Answer:  A, B, C, D

Diff: 3

Section:  5-3

Objective:  G2, G3

LO:  5.4

34) What is the value of ΔH in kcal/mole for the reaction shown?

(CH3)3C—H + Cl—Cl → (CH3)3C—Cl + H—Cl

Bond energies are: (CH3)3C—H = 91 kcal/mole

(CH3)3C—Cl = 78.5 kcal/mole

Cl—Cl = 58 kcal/mole

H—Cl = 103 kcal/mole

A) +32.5

B) -57.5

C) -32.5

D) +57.5

E) -8.5

Answer:  C

Diff: 2

Section:  5-4

Objective:  G2, G3

LO:  5.5

35) The Gibbs free energy equation models how free energy ΔG ________.

A) increases as both Keq and T increase

B) increases most when Keq  increases and T decreases

C) increases most when Keq  decreases and T increases

D) increases as both Keq  and T decrease

E) increases as reactant concentrations increase

Answer:  D

Diff: 2

Section:  5-4

Objective:  G2, G3

LO:  5.5

36) Which of the following correctly describes the reaction whose reaction coordinate diagram is shown?

A) endergonic with no transition state

B) exergonic with no transition state

C) endergonic with a transition state

D) exergonic with a transition state

E) endergonic with an intermediate

Answer:  D

Diff: 1

Section:  5-4

Objective:  G2, G3

LO:  5.5

37) What is the activation energy for the reaction B → A in the following diagram?

A) A

B) B

C) C

D) D

E) E

Answer:  E

Diff: 1

Section:  5-7

Objective:  G2, G3

LO:  5.9

38) Which of the following contributes to make ΔG° more negative?

A) use of a catalyst

B) a more positive ΔH°

C) a more positive ΔS°

D) a larger rate constant

E) none of the above

Answer:  C

Diff: 1

Section:  5-7

Objective:  G2, G3

LO:  5.9

39) Which of the following correctly describes intermediates and/or transition states?

A) Transition states occur at minima on reaction coordinate diagrams.

B) Both transition states and intermediates occur at maxima on reaction coordinate diagrams.

C) An intermediate is always produced after the rate-determining step of a reaction mechanism.

D) Transition states have partially formed bonds whereas intermediates have fully formed bonds.

E) none of the above

Answer:  D

Diff: 2

Section:  5-7

Objective:  G2, G3

LO:  5.9

40) Consider the reaction coordinate diagram shown. Which step has the greatest activation energy, assuming that this reaction is reversible and either the forward or reverse reaction is possible?

A) A going to C

B) C going to E

C) E going to G

D) E going to C

E) C going to A

Answer:  D

Diff: 2

Section:  5-7

Objective:  G2, G3

LO:  5.9

41) An increase in which of the following results in a decrease in the rate of the chemical reaction?

A) temperature

B) concentration

C) collision frequency

D) energy of activation

E) fraction of collisions with proper orientation

Answer:  D

Diff: 1

Section:  5-8

Objective:  G2, G3

LO:  5.10a

42) An increase in which of the following will occur if the reaction temperature is increased?

I. Energy of activation

II. Collision frequency

III. Fraction of collisions with sufficient energy

A) I and II

B) I and III

C) II and III

D) I, II, and III

E) I

Answer:  C

Diff: 2

Section:  5-8

Objective:  G2, G3

LO:  5.10a

43) Which of the following correctly describes the reaction shown?

A) ΔH° > 0 and ΔS° > 0

B) ΔH° > 0 and ΔS < 0

C) ΔH° < 0 and ΔS > 0

D) ΔH° < 0 and ΔS < 0

E) ΔH° = ΔS = 0

Answer:  D

Diff: 2

Section:  5-8

Objective:  G2, G3

LO:  5.10a

44) What is the molecular formula of the hydrocarbon that contains 5 carbon atoms, one ring, and one π bond?

Answer:  C5H8

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

45) What is the molecular formula of the hydrocarbon that contains 8 carbon atoms, one ring, and two π bonds?

Answer:  C8H12

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

46) Muscalure, the sex attractant of the common housefly, is an acyclic containing a single double bond and no triple bonds. If it contains 23 carbons, then how many hydrogen atoms are in a molecule of muscalure?

Answer:  46

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

47) Provide an acceptable name for the following compound.

Answer:  2-ethyl-5,5-dimethyl-1-hexene or 2-ethyl-5,5-dimethylhex-1-ene

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

48) Provide an acceptable name for the following compound.

 

Answer:  1,6-dibromocyclohexene

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

49) Draw the structure of vinyl bromide.

Answer:  CH2CHBr

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

50) Provide the IUPAC name for the alkene shown below.

Answer:  (E)-3,4-dimethyl-3-heptene

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

51) Provide the proper IUPAC name for the alkene shown below.

 

Answer:  6-bromo-1-methylcyclohexene

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

52) Draw and name the six alkenes which have the molecular formula C5H10.

Answer:  

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

53) Provide the systematic name of the alkene below.

Answer:  2-ethyl-1-hexene

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

54) Provide an acceptable name of the compound below.

Answer:  5-isobutyl-1-methylcyclopentene

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

55) Draw the structure of 1,3-cyclopentadiene.

Answer:  

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

56) Give the hybridization, shape, and bond angle for a carbon in ethene.

Answer:  sp2, trigonal planar, 120°

Diff: 1

Section:  5-1

Objective:  G2, G3

LO:  5.1

57) Draw (E)-2-methyl-3-hexen-1-ol.

Answer:  

 

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

58) Provide the systematic name of the compound shown below.  Make sure to include the E or Z designator if necessary.

Answer:  (E)-4-ethyl-3-nonene

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

59) Provide the systematic name of the compound shown below. Make sure to include the E or Z designator if necessary.

Answer:  (Z)-4-fluoro-3-heptene

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

60) Draw the structure of (Z)-1-chloro-2-methyl-2-butene.

Answer:  

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

61) Draw all the possible constitutional isomers of C4H8.

Answer:  

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

62) Draw the structure of two alkenes with molecular formula C4H8 that do not exhibit cis-trans isomerism.

Answer:  

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

63) Assign the E or Z configurational label to the following molecule:

 

Answer:  The molecule has a Z configuration based on the priority rule established by Cahn-Ingold-Prelog.

Diff: 2

Section:  5-1

Objective:  G2, G3

LO:  5.1

64) Draw the structure of (Z)-4-ethyl-3-methylheptene.

Answer:  

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

65) Draw the structure of (Z)-4-ethyl-3,6-dimethyl-3-heptene.

Answer:  

Diff: 3

Section:  5-1

Objective:  G2, G3

LO:  5.1

66) Draw the curved arrows to show how CH3CH=CHCH3 reacts with HBr to form a carbocation.

Answer:  

Diff: 2

Section:  5-3

Objective:  G2, G3

LO:  5.4

67) Give the mechanism for the following reaction.

Answer:  

Diff: 3

Section:  5-3

Objective:  G2, G3

LO:  5.4

68) Identify the nucleophiles and electrophiles.

-OH, BH3, H2O, +CH3, NH3, Br- 

Answer:  

nucleophiles:  -OH, H2O, NH3, Br- 

electrophiles:  BH3, +CH3

Diff: 1

Section:  5-3

Objective:  G2, G3

LO:  5.3

69) Calculate the enthalpy for the following reaction.

DH

CH2CH2, 62 kcal/mole

H-Cl, 103 kcal/mole

CH3CH2-H, 101 kcal/mole

CH3CH2-Cl, 85 kcal/mole

Answer:  -21 kcal/mole

Diff: 3

Section:  5-4

Objective:  G2, G3

LO:  5.5

70) Consider the single step interconversion of A and B shown below. How is the equilibrium constant K related to the rate constants k1 and k-1 and to the amounts of A and B present at equilibrium?

Answer:  K =  = 

Diff: 3

Section:  5-4

Objective:  G2, G3

LO:  5.5

71) If the temperature of a given reaction is doubled, how will the Gibbs free energy of the reaction change? 

Answer:  The Gibbs free energy will also increase by a factor of 2.

Diff: 3

Section:  5-4

Objective:  G2, G3

LO:  5.5

72) Consider the conversion of C to D via a one-step mechanism. The activation energy of this conversion is 3 kcal/mol. The energy difference between D and the transition state of the reaction is 7 kcal/mol. Estimate ΔH° for the reaction C → D.

Answer:  4 kcal/mol

Diff: 3

Section:  5-6

Objective:  G2, G3

LO:  5.8

73) Consider the one-step conversion of F to G. Given that the reaction is endergonic by 5 kcal/mol and that the energy difference between G and the transition state for the process is 15 kcal/mol, sketch a reaction-energy profile for this reaction. Make sure to show how the given energy differences are consistent with your sketch.

Answer:  

Diff: 3

Section:  5-6

Objective:  G2, G3

LO:  5.8

74) The ΔG° for the conversion of “axial” isopropylcyclohexane to “equatorial” isopropylcyclohexane at 298K is -2.1 kcal/mol. Calculate the percentage of isopropylcyclohexane molecules that have the isopropyl substituent in the axial position at this temperature. 

[R = 1.987 × 10-3 kcal mol-1K-1]

Answer:  

ΔG° = -RTlnK

-2.1 kcal/mol = -(1.987 × 10-3 kcal mol-1 K-1)(298K)lnK

lnK = 

K =  = 34.7

% axial =  × 100%

=  × 100%

= 2.8%

Diff: 3

Section:  5-7

Objective:  G2, G3

LO:  5.9

75) Based on the following energy diagram, which compound, A or C, is formed faster from B? Which is more stable, A or C? Explain.

Answer:  A is formed faster since the pathway for its formation has the smaller activation energy. C is more stable than A because it has a lower energy.

Diff: 3

Section:  5-7

Objective:  G2, G3

LO:  5.9

76) Under what conditions is ΔG° equal to ΔH° for a chemical reaction?

Answer:  Since ΔG° = ΔH° – TΔS°, then ΔG° is equal to ΔH° when TΔS° is zero.

Diff: 3

Section:  5-8

Objective:  G2, G3

LO:  5.10a

77) Why do reactions tend to proceed at a faster rate as T increases?

Answer:  The number of molecular collisions that possesses sufficient energy to overcome the barrier to reaction increases.

Diff: 3

Section:  5-8

Objective:  G2, G3

LO:  5.10a

78) What is the free energy of activation of a one-step reaction? How is it qualitatively related to the rate constant of the reaction?

Answer:  The free energy of activation of a one-step reaction is the difference in free energy between the transition state and the reactants. As the free energy of activation increases, the rate constant decreases.

Diff: 3

Section:  5-8

Objective:  G2, G3

LO:  5.10a

79) Consider the reaction coordinate diagram shown. Which letters designate intermediates?

Answer:  C and E

Diff: 2

Section:  5-9

Objective:  G2, G3

LO:  5.12

80) Consider the reaction coordinate diagram shown. Which step has the greatest rate constant in the forward direction?

Answer:  Step 3 (E going to G)

Diff: 2

Section:  5-9

Objective:  G2, G3

LO:  5.12

81) Consider the reaction coordinate diagram shown.  What is the rate-determining step in the conversion of A to G?

Answer:  Step 2 (C going to E)

Diff: 2

Section:  5-9

Objective:  G2, G3

LO:  5.12

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