Organic Chemistry 8th Edition by Bruice – Test Bank

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Organic Chemistry, 8e (Bruice)

Chapter 5   Alkenes: Structure, Nomenclature, and an Introduction to Reactivity – Thermodynamics and Kinetics

 

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

Answer:  C5H8

Section:  5-1

GLO:  G2

 

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

Answer:  C8H12

Section:  5-1

GLO:  G2

 

3) Give the general formula for a cyclic alkene.

  1. A) CnH2n-4
  2. B) CnH2n-2
  3. C) CnH2n
  4. D) CnH2n+2

Answer:  B

Section:  5-1

 

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

  1. A) no rings, no double bonds, no triple bonds
  2. B) one double bond, or one ring
  3. C) two rings, two double bonds, one double bond + one ring, or one triple bond
  4. 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
  5. E) benzene

Answer:  C

Section:  5-1

 

5) Give the degree of unsaturation for benzene.

  1. A) 1
  2. B) 2
  3. C) 3
  4. D) 4
  5. E) 5

Answer:  D

Section:  5-1

 

6) 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?

  1. A) 0
  2. B) 1
  3. C) 2
  4. D) 3
  5. E) 4

Answer:  B

Section:  5-1

 

7) A hydrocarbon with molecular formula C20H34 has what degree of substitution?

  1. A) 2
  2. B) 3
  3. C) 4
  4. D) 5
  5. E) 6

Answer:  C

Section:  5-1

MCAT:  3.1

 

8) Muscalure, the sex attractant of the common housefly, is an acyclic alkene that contains 23 carbons. How many hydrogen atoms are in a molecule of muscalure?

Answer:  46

Section:  5-1

 

9) Provide an acceptable name for the following compound.

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

Section:  5-2

 

 

10) Provide an acceptable name for the following compound.

Answer:  1,6-dibromocyclohexene

Section:  5-2

MCAT:  3.1, 6.1

11) Name the structure.

  1. A) 2-ethyl-1-pentene
  2. B) 2-propyl-1-butene
  3. C) 3-methylenehexane
  4. D) 3-methyl-3-hexene
  5. E) ethyl propyl ethene

Answer:  A

Section:  5-2

MCAT:  7.1

 

12) Name the structure.

  1. A) 2-methyl-2,4-pentadiene
  2. B) 4-methyl-1,4-pentadiene
  3. C) 2-methylene-4-pentene
  4. D) 4-methylene-2-pentene
  5. E) 2-methyl-1,4-pentadiene

Answer:  E

Section:  5-2

MCAT:  7.1

 

 

13) Name the structure.

  1. A) 7-chloro-3-ethyl-4-methyl-3-heptene
  2. B) 1-chloro-5-ethyl-4-methyl-3-heptene
  3. C) 1-chloro-3-pentenyl-2-pentene
  4. D) cis-7-chloro-3-ethyl-4-methyl-3-heptene
  5. E) trans-7-chloro-3-ethyl-4-methyl-3-heptene

Answer:  A

Section:  5-2

MCAT:  6.1, 7.1

14) Name the structure.

  1. A) 4-chlorocyclohexene
  2. B) 1-chloro-3-cyclohexene
  3. C) 1-chloro-3-cycloheptene
  4. D) 4-chlorocycloheptane
  5. E) 4-chlorocycloheptene

Answer:  E

Section:  5-2

MCAT:  6.1, 7.1

 

15) Draw vinyl bromide.

Answer:  CH2CHBr

Section:  5-2

MCAT:  6.1, 7.1

 

16) Name the structure.

H2CCHCH2I

  1. A) vinyl iodide
  2. B) allyl iodide
  3. C) 1-iodo-2-propene
  4. D) iodomethylethene
  5. E) 2-iodo-1-propene

Answer:  B

Section:  5-2

MCAT:  6.1, 7.1

 

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

  1. A) t-butylene
  2. B) sec-butylene
  3. C) isobutylene
  4. D) butylene
  5. E) methylpropylene

Answer:  C

Section:  5-2

MCAT:  7.1

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

  1. A) 2-methyl-1-butene
  2. B) isopentene
  3. C) 2-methybutene
  4. D) 2-ethylpropene
  5. E) 3-methyl-3-butene

Answer:  A

Section:  5-2

MCAT:  7.1

 

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

  1. A) 5-methylcyclohexene
  2. B) 4-methylcyclohexene
  3. C) 1-methyl-3-cyclohexene
  4. D) 1-methyl-4-cyclohexene
  5. E) methylcyclohexene

Answer:  B

Section:  5-2

MCAT:  7.1

 

 

20) Which of the following is vinyl chloride?

  1. A) CH3CH2Cl
  2. B) CH2CHCH2Cl
  3. C) CH2CHCl
  4. D)
  5. E)

Answer:  C

Section:  5-2

MCAT:  6.1, 7.1

21) Which of the following is an allylic alcohol?

  1. A) CH2CHCH2OCH3
  2. B) CH2CHCH2CH3
  3. C) HOCHCHCH2CH3
  4. D) CH3CHCHCH2OH
  5. E) CH2CHCH2CH2OH

Answer:  D

Section:  5-2

MCAT:  7.1, 10.1

 

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

Answer:  (E)-3,4-dimethyl-3-heptene

Section:  5-2

MCAT:  7.1, 7.3

 

 

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

Answer:  6-bromo-1-methylcyclohexene

Section:  5-2

MCAT:  6.1, 7.1

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

Answer:

Section:  5-2

MCAT:  1.1, 3.2

 

25) Provide the systematic name of the alkene below.

Answer:  2-ethyl-1-hexene

Section:  5-2

MCAT:  7.1

 

 

26) Provide an acceptable name of the compound below.

Answer:  5-isobutyl-1-methylcyclopentene

Section:  5-2

MCAT:  7.1

 

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

  1. A) The H-C-H bond angles are approximately 109.5°.
  2. B) All of the hydrogen atoms are in the same plane.
  3. C) There is a total of five sigma bonds.
  4. D) The carbon atoms are sp2
  5. E) The H-C-H bond angles are approximately 120°.

Answer:  A

Section:  5-3

MCAT:  2.2, 7.5

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

  1. A) All nine atoms lie in the same plane.
  2. B) The compound has a cis and trans isomer.
  3. C) It generally acts as a Lewis acid.
  4. D) There is a total of eight sigma bonds.
  5. E) All the carbon atoms are sp2

Answer:  D

Section:  5-3

MCAT:  7.5

 

29) Draw the structure of propyl vinyl ether.

Answer:

Section:  5-2

MCAT:  7.1, 14.1

 

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

Answer:  sp2, trigonal planar, 120°

Section:  5-3

 

 

31) Name the structure.

  1. A) cis-3-ethyl-4-hydroxymethyl-hex-3-en-1-yne
  2. B) cis-2,3-diethylpent-2-en-4-yn-1-ol
  3. C) trans-2,3-diethylpent-2-en-4-yn-1-ol
  4. D) cis-3,4-diethylpent-3-en-1-yn-5-ol
  5. E) trans-3,4-diethylpent-3-en-1-yn-5-ol

Answer:  C

Section:  5-2

MCAT:  7.1, 7.3, 9.1

 

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

  1. A) 0
  2. B) 1
  3. C) 2
  4. D) 3
  5. E) 4

Answer:  C

Section:  5-3

MCAT:  7.1

33) Name the structure.

  1. A) cis-4,5-dimethyl-4-hepten-1-ol
  2. B) trans-3,4-dimethyl-3-hepten-7-ol
  3. C) cis-3,4-dimethyl-3-hepten-7-ol
  4. D) trans-4,5-dimethyl-4-hepten-1-ol
  5. E) trans-4,5-dimethyl-4-heptenol

Answer:  D

Section:  5-2

MCAT:  7.1, 7.3, 10.1

 

 

34) Name the structure.

  1. A) (Z)-4,5-dimethyl-4-hepten-1-ol
  2. B) (E)-4,5-dimethyl-4-hepten-1-ol
  3. C) (E)-3,4-dimethyl-3-hepten-7-ol
  4. D) (Z)-3,4-dimethyl-3-hepten-7-ol
  5. E) (E)-4,5-dimethyl-4-heptenol

Answer:  B

Section:  5-2

MCAT:  7.1, 7.3, 10.1

 

35) Name the structure.

  1. A) (Z)-3-ethyl-2-hydroxymethyl-2-penten-4-ynal
  2. B) (E)-3-ethyl-2-hydroxymethyl-2-penten-4-ynal
  3. C) (Z)-3-ethyl-5-hydroxymethyl-3-penten-1-ynal
  4. D) (E)-3-ethyl-5-hydroxymethyl-3-penten-1-ynal
  5. E) 3-ethyl-5-hydroxymethyl-3-penten-1-ynal

Answer:  A

Section:  5-2

MCAT:  7.1, 9.1, 18.1

 

36) Name the structure.

  1. A) (2E,4E)-7-chloro-2,4-heptadiene
  2. B) (2Z,4E)-7-chloro-2,4-heptadiene
  3. C) (2Z,4Z)-7-chloro-2,4-heptadiene
  4. D) (2E,4Z)-7-chloro-2,4-heptadiene
  5. E) 7-chloro-2,4-heptadiene

Answer:  D

Section:  5-2

MCAT:  6.1, 7.1

 

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

Answer:

Section:  5-2

MCAT:  7.1, 10.1

 

38) 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

Section:  5-2

MCAT:  7.1, 7.3

 

39) 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

Section:  5-2

 

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

Answer:

Section:  5-2

MCAT:  6.1, 7.1, 7.3

 

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

  1. A) 1-butene
  2. B) 1-pentene
  3. C) cyclohexene
  4. D) ethene
  5. E) 2-butene

Answer:  E

Section:  5-2

MCAT:  7.5

 

42) Draw all the possible constitutional isomers of C4H8.

Answer:

Section:  5-2

MCAT:  1.1, 3.2

 

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

Answer:

Section:  5-2

MCAT:  3.2

GLO:  G2

 

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

  1. A) E
  2. B) Z
  3. C) neither E nor Z

Answer:  C

Section:  4-2

MCAT:  7.3

 

45) 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.

Section:  4-2

MCAT:  7.3

 

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

Answer:

Section:  5-2

MCAT:  7.3

 

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

Answer:

Section:  5-2

MCAT:  7.3

 

48) Which of the following is not an electrophile?

  1. A) H+
  2. B) BF3
  3. C) +NO2
  4. D) Fe+3
  5. E) CH2CH2

Answer:  E

Section:  5-5

MCAT:  1.4

 

49) Which of the following is not a nucleophile?

  1. A) FeBr3
  2. B) Br-
  3. C) NH3
  4. D)
  5. E) CH3OCH3

Answer:  A

Section:  5-5

MCAT:  1.4

 

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

Answer:

Section:  5-5

MCAT:  1.4

 

51) Give the mechanism for the following reaction.

Answer:

Section:  5-5

MCAT:  1.4

 

52) Identify the nucleophiles and electrophiles.

-OH, BH3, H2O, +CH3, NH3, Br-

Answer:  nucleophiles: -OH, H2O, NH3, Br-

electrophiles: BH3, +CH3

Section:  5-5

MCAT:  1.4

53) Calculate the enthalpy for the following reaction.

H-Cl, 103 kcal/mole

CH3CH2-H, 101 kcal/mole

CH3CH2-Cl, 85 kcal/mole

Answer:  -21 kcal/mole

Section:  5-8

GLO:  G4

 

54) 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

  1. A) +32.5
  2. B) -57.5
  3. C) -32.5
  4. D) +57.5
  5. E) -8.5

Answer:  C

Section:  5-8

GLO:  G4

 

 

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

  1. A) 3
  2. B) 4
  3. C) 5
  4. D) 2
  5. E) 1

Answer:  D

Section:  5-12

GLO:  G3, G4

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

  1. A) temperature
  2. B) concentration
  3. C) collision frequency
  4. D) energy of activation
  5. E) fraction of collisions with proper orientation

Answer:  D

Section:  5-11

GLO:  G2

 

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

  1. Energy of activation
  2. Collision frequency

III. Fraction of collisions with sufficient energy

  1. A) I and II
  2. B) I and III
  3. C) II and III
  4. D) I, II, and III
  5. E) I

Answer:  C

Section:  5-11

GLO:  G2

 

 

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

  1. A) A
  2. B) B
  3. C) C
  4. D) D
  5. E) E

Answer:  E

Section:  5-10

 

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

  1. A) use of a catalyst
  2. B) a more positive ΔH°
  3. C) a more positive ΔS°
  4. D) a larger rate constant
  5. E) none of the above

Answer:  C

Section:  5-10

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

  1. A) Transition states occur at minima on reaction coordinate diagrams.
  2. B) Both transition states and intermediates occur at maxima on reaction coordinate diagrams.
  3. C) An intermediate is always produced after the rate-determining step of a reaction mechanism.
  4. D) Transition states have partially formed bonds whereas intermediates have fully formed bonds.
  5. E) none of the above

Answer:  D

Section:  5-12

 

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

  1. A) ΔH° >0 and ΔS° >0
  2. B) ΔH° >0 and ΔS <0
  3. C) ΔH° <0 and ΔS >0
  4. D) ΔH° <0 and ΔS <0
  5. E) ΔH° = ΔS = 0

Answer:  D

Section:  5-6

GLO:  G3

 

62) 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.

Section:  5-6

GLO:  G2

 

63) 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

Section:  5-6

GLO:  G4

64) 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:

Section:  5-6

GLO:  G2, G3

 

 

65) 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%

Section:  5-6

66) 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.

Section:  5-6, 5-10

GLO:  G3

 

67) 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 =  =

Section:  5-11

GLO:  G4

 

68) 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.

Section:  5-11

 

69) The Arrhenius equation models how the rate constant k

  1. A) increases as both Eaand T increase.
  2. B) increases most when Eaincreases and T decreases.
  3. C) increases most when Eadecreases and T increases.
  4. D) increases as both Eaand T decrease.
  5. E) increases as reactant concentrations increase.

Answer:  C

Section:  5-11

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

  1. A) endergonic with no transition state
  2. B) exergonic with no transition state
  3. C) endergonic with a transition state
  4. D) exergonic with a transition state
  5. E) endergonic with an intermediate

Answer:  D

Section:  5-6

GLO:  G3

 

71) Given an activation energy of 15 kcal/mol, use the Arrhenius equation to estimate how much faster the reaction will occur if the temperature is increased from 100°C to 120°C. R = 1.987 cal/mol ∙ K.

Answer:  The reaction will occur about 2.8 times faster.

Section:  5-11

GLO:  G4

 

 

72) 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.

Section:  5-10

73) Consider the reaction coordinate diagram shown. Which step has the greatest activation energy?

  1. A) A going to C
  2. B) C going to E
  3. C) E going to G
  4. D) E going to C
  5. E) C going to A

Answer:  D

Section:  5-12

GLO:  G3

 

 

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

Answer:  C and E

Section:  5-12

GLO:  G3

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

Answer:  Step 3 (E going to G)

Section:  5-12

GLO:  G3

 

 

76) 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)

Section:  5-12

GLO:  G3

77) How many degrees of unsaturation are present in a molecule with formula C10H16?

  1. A) 1
  2. B) 2
  3. C) 3
  4. D) 4
  5. E) 5

Answer:  C

Section:  5-1

 

78) Linalool is a major compound present in the essential oil of coriander. How many degrees of unsaturation are present in this molecule?

  1. A) 2
  2. B) 3
  3. C) 4
  4. D) 5
  5. E) 6

Answer:  A

Section:  5-1

 

 

79) How many degrees of unsaturation are present in this molecule?

  1. A) 1
  2. B) 2
  3. C) 3
  4. D) 4
  5. E) 5

Answer:  D

Section:  5-1

 

80) Provide the proper IUPAC name of the following compound

Answer:  (Z)-3-methylhex-3-ene

Section:  5-2

MCAT:  7.3

81) Using curved arrows show the movement of electrons in the following reaction.

Answer:

Section:  5-5

MCAT:  1.4

 

 

82) Indicate the electrophile and nucleophile in the chemical reaction?

Answer:

Section:  5-5

MCAT:  1.4

 

83) A carbocation is

  1. A) a carbon with a negative charge
  2. B) a carbon with a positive charge
  3. C) a carbon with an unpaired electron
  4. D) a carbon with complete octet
  5. E) a carbon with five hydrogens

Answer:  B

Section:  5-5

MCAT:  4.2

 

84) The rate determining step of a reaction is the

  1. A) slowest step and thus, has highest energy barrier
  2. B) slowest step and thus, has lowest energy barrier
  3. C) fastest step and thus, has highest energy barrier
  4. D) fastest step and thus, has lowest energy barrier
  5. E) none of the above

Answer:  A

Section:  5-12

 

 

 

 

Organic Chemistry, 8e (Bruice)

Chapter 18   Reactions of Benzene and Substituted Benzenes

 

1) Provide the structure of anisole.

Answer:

Section:  18-1

MCAT:  16.4

 

2) Provide the structure of benzenesulfonic acid.

Answer:

Section:  18-1

MCAT:  16.4

 

3) Provide the structure of dibenzyl ether.

Answer:

Section:  18-1

MCAT:  16.4

 

4) Name the following compound.

 

  1. A) sec-hexylbenzene
  2. B) 3-phenylhexane
  3. C) 2-phenylhexane
  4. D) tert-hexylbenzene
  5. E) isohexylbenzene

Answer:  C

Section:  18-1

MCAT:  16.4

 

5) Draw benzyl bromide.

Answer:

Section:  18-1

MCAT:  16.4

 

6) What is the structure of styrene?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  A

Section:  18-1

MCAT:  16.4

 

7) Which of the following is not a correct statement about the electrophilic substitution mechanism of benzene?

  1. A) Benzene functions as a nucleophile.
  2. B) Formation of a carbocation intermediate is the rate-determining step.
  3. C) The carbocation intermediate contains an sp3hybridized carbon in the ring.
  4. D) The addition product is a frequent minor product.
  5. E) Aromaticity is regained by loss of H+.

Answer:  D

Section:  8-21

MCAT:  16.5, 17.1

 

8) Why does benzene undergo electrophilic substitution rather than electrophilic addition?

Answer:  When benzene undergoes electrophilic substitution, the product retains the stability associated with an aromatic system. This stability is lost in electrophilic addition because the product is not aromatic.

Section:  8-21

MCAT:  16.5, 17.1

GLO:  G2, G8

 

9) Which of the following is most likely to be the first step in the general mechanism for electrophilic substitution reactions?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  B

Section:  18-2

MCAT:  1.4, 16.5, 17.1

 

10) Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E+.

Answer:

Section:  18-2

MCAT:  17.1

 

11) In the bromination of benzene using Br2 and FeBr3, is the intermediate carbocation aromatic? Explain.

Answer:  No, the carbocation is not aromatic since the ring contains an sp3 center.

Section:  18-3

GLO:  G8

 

12) Which step in the general mechanism for electrophilic aromatic substitution is rate-determining? Explain.

Answer:  The first step involves addition of the electrophile to benzene to yield a nonaromatic cationic intermediate. The second step involves the loss of H+ from this cationic intermediate to yield an aromatic product. The rate-determining or slow step is the one in which the aromatic reagent is converted into a much less stable nonaromatic cation.

Section:  18-2

13) Which of the following is one of the resonance contributors of the intermediate produced in a Friedel-Crafts alkylation of benzene?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  A

Section:  18-2

MCAT:  17.1

 

14) Which of the following is the first step in the mechanism of bromination?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  C

Section:  18-3

MCAT:  17.1

 

15) What purpose does FeCl3 serve in the electrophilic aromatic substitution reaction between chlorine and benzene?

  1. A) It serves as a radical initiator to produce the chlorine radical needed to propagate the chain reaction.
  2. B) It functions by destabilizing the carbocationic intermediate and thereby increases the rate of H+
  3. C) It serves as a Lewis base catalyst by reacting with Cl2to generate chloride ions.
  4. D) It functions by destabilizing the benzene through formation of a π-complex.
  5. E) It serves as a Lewis acid catalyst by reacting with the Cl2and thereby activates it toward attack by benzene’s π electrons.

Answer:  E

Section:  18-3

MCAT:  1.4

 

16) Provide a detailed, stepwise mechanism for the reaction of benzene with Br2 and FeBr3. Make sure to include the activating reaction between Br2 and FeBr3 in your mechanism.

Answer:

Section:  18-3

MCAT:  1.4, 17.1

 

17) Bromination of benzene requires a Lewis acid catalyst while bromination of cyclohexene does not. Explain this difference in reactivity.

Answer:  An alkene is a better nucleophile than benzene, and thus the Br-Br bond does not have to be weakened to form a better electrophile before reaction.

Section:  18-4

MCAT:  1.4, 16.5

 

18) Give the best product for the following reaction.

Answer:

Section:  18-3

 

19) Which of the following is the electrophile that attacks the aromatic ring during nitration?

  1. A) NO2
  2. B) HNO3
  3. C) HNO3-
  4. D) NO2+
  5. E) NO2-

Answer:  D

Section:  18-4

 

20) What specific electrophile is attacked by benzene when it undergoes nitration?

  1. A) HNO3
  2. B) NO3
  3. C) NO
  4. D) NO2
  5. E) NO2+

Answer:  E

Section:  18-4

 

 

21) Identify the best product for the following reaction.

  1. A)
  2. B)
  3. C)
  4. D)
  5. E)

Answer:  A

Section:  18-4

 

22) Predict the major organic product of the following reaction.

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  D

Section:  18-5

 

23) Which of the following is the electrophile that attacks the aromatic ring during sulfonation?

  1. A) HSO3+
  2. B) SO2+
  3. C) HSO3-
  4. D) H2SO4
  5. E) HSO4-

Answer:  A

Section:  18-5

 

24) Name the major organic product which results when 4-ethylbenzenesulfonic acid is heated in aqueous acid.

Answer:  ethylbenzene

Section:  18-5

 

25) What is the principle of microscopic reversibility?

Answer:  This principle states that the mechanism of a reaction in the reverse direction must retrace each step of the mechanism in the forward direction in microscopic detail. Both the forward and reverse reactions must have the same intermediates and transition states.

Section:  18-5

GLO:  G8

 

26) Identify the best product for the following reaction.

  1. A)
  2. B)
  3. C)
  4. D)
  5. E)

Answer:  A

Section:  18-5

 

27) Which of the following is not a correct statement concerning the Friedel-Crafts acylation of benzene?

  1. A) An alkyl group substitutes for a hydrogen.
  2. B) The benzene ring attacks an acylium ion.
  3. C) The acylium ion is resonance stabilized.
  4. D) The acylium ion is often produced from an acyl chloride.
  5. E) More than one equivalent of Lewis acid must be used.

Answer:  A

Section:  18-6

 

28) Which of the following is the electrophile that attacks the aromatic ring during Friedel-Crafts acylation?

  1. A)
  2. B)
  3. C)
  4. D)
  5. E) AlCl3

Answer:  B

Section:  18-6

 

29) Why must Friedel-Crafts acylation reactions be run with more than a single equivalent of AlCl3?

Answer:  These reactions must be run with more than one equivalent of AlCl3 because the product of the reaction contains a carbonyl group that can complex with AlCl3.

Section:  18-6

GLO:  G2, G8

 

30) Provide the major organic product of the reaction shown below.

Answer:

Section:  18-22

 

 

31) Identify the best product for the following reaction.

  1. A)
  2. B)
  3. C)
  4. D)

 

  1. E)

Answer:  E

Section:  18-6

 

 

32) Identify the best product for the following reaction.

  1. A)
  2. B)
  3. C)
  4. D)

 

  1. E)

Answer:  D

Section:  18-6

33) What is the major product of the following Friedel-Crafts alkylation?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  C

Section:  18-7

 

 

34) What is the major organic product of the reaction between benzene and isobutyl chloride in the presence of AlCl3?

  1. A) tert-butylbenzene
  2. B) isobutylbenzene
  3. C) n-butylbenzene
  4. D) chlorobenzene
  5. E) sec-butylbenzene

Answer:  A

Section:  18-7

35) Provide the major organic product of the reaction shown below.

Answer:

Section:  18-22

 

36) Provide the major organic product of the reaction shown below.

Answer:

Section:  18-7

 

 

37) Provide the major organic product of the reaction shown below.

Answer:

Section:  18-7

38) Provide the structure of the major organic product of the following reaction.

Answer:

Section:  18-7

 

 

39) Provide the major organic product of the following.

Answer:

Section:  18-7

 

 

40) Identify the major product for the following reaction.

  1. A)
  2. B)
  3. C)
  4. D)

 

  1. E)

Answer:  E

Section:  18-7

41) What is the major organic product that results when benzene is treated with 1-chlorobutane and AlCl3?

  1. A) ethylbenzene
  2. B) 1-propylbenzene
  3. C) butylbenzene
  4. D) sec-butylbenzene
  5. E) isobutylbenzene

Answer:  D

Section:  18-7

 

42) Provide the major organic product of the following.

Answer:

Section:  18-8

 

43) What is the major organic product of the reaction shown below?

Answer:

Section:  18-8

 

44) Identify the condition(s) that will not work for the following reaction. You may choose more than one answer.

  1. A)
  2. B)
  3. C)
  4. D) CH3CH2CH2Cl + AlCl3
  5. E) CH3CH2CH2OH, H2SO4

Answer:  D, E

Section:  18-7

 

 

45) What is the major organic product of the reaction shown below?

Answer:

Section:  18-9

46) What is the major organic product of the reaction shown below?

Answer:

Section:  18-9

 

 

47) Identify the best product for the following reaction.

  1. A)

+ LiBr

  1. B)
  2. C)
  3. D)

 

  1. E)

Answer:  A

Section:  18-9

 

48) Give the organic products from the following reaction.

Answer:

Section:  18-9

49) Give the organic products from the following reaction.

Answer:

Section:  18-9

 

 

50) What is the major product of the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  D

Section:  18-10

 

51) What is the major product of the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  A

Section:  18-10

 

52) What is the major product of the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  E

Section:  18-10

 

53) Benzene can be reduced to cyclohexane when it is treated with hydrogen in the presence of a nickel catalyst under conditions of high temperature and pressure. Predict the signs of ΔH° and ΔS° for this process.

  1. A) ΔH° > 0, ΔS° > 0
  2. B) ΔH° > 0, ΔS° < 0
  3. C) ΔH° > 0, ΔS° = 0
  4. D) ΔH° < 0, ΔS° > 0
  5. E) ΔH° < 0, ΔS° < 0

Answer:  E

Section:  18-10

MCAT:  16.5

 

54) Which of the following fails to produce benzoic acid when heated in the presence of acidic sodium dichromate?

  1. A) 1-phenylethanol
  2. B) 2-phenylethanol
  3. C) 2-phenylheptane
  4. D) 2-methyl-2-phenylheptane
  5. E) 1-phenylheptanol

Answer:  D

Section:  18-10

MCAT:  20.1

 

55) Provide the structure of the major organic product of the following reaction sequence.

Answer:

Section:  18-10

 

56) Provide the structure of the major organic product of the following reaction.

Answer:

Section:  18-10

MCAT:  11.1

 

 

57) Identify the product(s) for the following reaction.

  1. A)
  2. B)
  3. C)
  4. D)
  5. E)

Answer:  D

Section:  18-13

 

58) Identify the best product for the following reaction.

 

  1. A)
  2. B)
  3. C)
  4. D)

 

  1. E)

Answer:  C

Section:  18-16

 

 

59) Identify the best product for the following reaction.

  1. A)
  2. B)
  3. C)
  4. D)
  5. E)

Answer:  B

Section:  18-10

60) Identify the reaction(s) below that give benzoic acid as a product. You may choose more than one answer.

  1. A) 1-phenylethanol + manganese dioxide + heat
  2. B) 1-phenylethanol + sodium dichromate + acid + heat
  3. C) tert-butylbenzene + sodium dichromate + acid + heat
  4. D) ethylbenzene + sodium dichromate + acid + heat
  5. E) phenylmethanol + manganese dioxide + heat

Answer:  B, D

Section:  18-10

MCAT:  11.1

 

 

61) Identify the best product for the following reaction.

  1. A)
  2. B)
  3. C)
  4. D)
  5. E)

Answer:  C

Section:  18-10

 

 

62) Give the best product for the following reaction.

Answer:

Section:  18-10

 

63) Give the best product for the following reaction.

Answer:

Section:  18-16

 

64) What is the structure of phenol?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  D

Section:  18-1

MCAT:  10.1

 

65) What is the name of the following compound?

  1. A) m-bromomethylbenzene
  2. B) m-bromotoluene
  3. C) 3-bromotoluene
  4. D) A and B
  5. E) B and C

Answer:  E

Section:  18-11

MCAT:  16.4

 

66) What is the structure of 3-phenylpentane?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  E

Section:  18-11

MCAT:  16.4

 

67) The name 2,4,6-tribromobenzene is incorrect. Which of the following is the correct name?

  1. A) tribromobenzene
  2. B) m,m-dibromobromobenzene
  3. C) 3,5-dibromobromobenzene
  4. D) 1,3,5-tribromobenzene
  5. E) m,m,m-tribromobenzene

Answer:  D

Section:  18-11

MCAT:  16.4

 

68) What is the name of the following compound?

  1. A) p-dichlorobenzene
  2. B) 1,4-dichlorobenzene
  3. C) phenyldichloride
  4. D) A and B
  5. E) B and C

Answer:  D

Section:  18-11

MCAT:  16.4

 

69) What is the structure of p-toluidine?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  C

Section:  18-11

MCAT:  16.4

 

70) What is the name of the following compound?

  1. A) o-nitro-m-bromotoluene
  2. B) 3-bromo-6-nitrotoluene
  3. C) m-bromo-o-nitrotoluene
  4. D) 5-bromo-2-nitrotoluene
  5. E) 2-nitro-5-bromotoluene

Answer:  D

Section:  18-11

MCAT:  16.4

 

71) What is the proper name of the compound below?

  1. A) 1-phenoxyethane
  2. B) ethyl phenyl ether
  3. C) m-butylhydroxybenzene
  4. D) o-butylhydroxybenzene
  5. E) m-butylphenol

Answer:  E

Section:  18-11

MCAT:  16.4

 

72) How many signals does one expect in the proton decoupled 13C NMR spectrum of o-xylene?

  1. A) 8
  2. B) 6
  3. C) 4
  4. D) 3
  5. E) 2

Answer:  C

Section:  14-20, 18-11

MCAT:  16.6

 

73) Provide the structure of benzoic acid.

Answer:

Section:  18-11

MCAT:  16.4

 

74) Provide the structure of anisole.

Answer:

Section:  18-1

MCAT:  16.4

 

75) Can one distinguish among the three isomeric xylenes using 13C NMR? Explain.

Answer:  Yes. In the proton decoupled 13C NMR spectra of these three isomers, different numbers of peaks are present. The ortho isomer has 4, the meta isomer has 5, and the para isomer has 3.

Section:  18-11, 14-20

MCAT:  16.6

 

76) Provide the best name for the organic compound below.

Answer:  o-propylphenol or 2-propylphenol

Section:  18-11

MCAT:  16.4

 

77) Provide the best name for the organic compound below.

Answer:  m-toluidine

Section:  18-11

MCAT:  16.4

 

78) Name the following structure.

 

  1. A) 2-chlorobenzoic acid
  2. B) 3-chlorobenzoic acid
  3. C) 2-chlorobenzaldehyde
  4. D) 3-chlorobenzaldehyde
  5. E) 3-chloroacetophenone

Answer:  B

Section:  18-11

MCAT:  16.4

 

79) Give the best name for the structure.

  1. A) 2-methyl-1,3,5-trinitrobenzene
  2. B) 1,3,5-triaminotoluene
  3. C) 1,3,5-trinitrotoluene
  4. D) 2,4,6-triaminotoluene
  5. E) 2,4,6-trinitrotoluene

Answer:  E

Section:  18-11

MCAT:  16.4

 

80) Give three different correct names for the structure.

Answer:  2-amino-4-methylphenol

2-hydroxy-5-methylaniline

3-amino-4-hydroxytoluene

Section:  18-11

MCAT:  16.4

 

81) Draw p-aminobenzoic acid.

Answer:

Section:  18-11

MCAT:  16.4

 

82) Which of the following compounds reacts most slowly during nitration?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  C

Section:  18-12

MCAT:  17.2

 

83) Which of the following compounds reacts most rapidly during nitration?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  D

Section:  18-12

MCAT:  17.2

 

84) Which of the following substrates is an electron donating group overall?

  1. A) –Br
  2. B)
  3. C) –OCH3
  4. D)
  5. E) –CCl3

Answer:  C

Section:  18-12

MCAT:  17.2

 

85) Which of the following substrates is an electron withdrawing group overall?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  E

Section:  18-12

MCAT:  17.2

 

86) Which of the following substituents acts as a moderate activator and o/p director in electrophilic aromatic substitution reactions?

  1. A) -Br
  2. B) -SO3H
  3. C) -CO2H
  4. D) -NHCOR
  5. E) -CHO

Answer:  D

Section:  18-12

MCAT:  17.2

 

87) Which of the following aromatic rings is alkylated most rapidly by CH3CH2Cl/AlCl3?

  1. A) benzene
  2. B) ethylbenzene
  3. C) chlorobenzene
  4. D) benzenesulfonic acid
  5. E) nitrobenzene

Answer:  B

Section:  18-12

MCAT:  17.2

 

88) Rank the following groups in order of increasing activating power in electrophilic aromatic substitution reactions:

-OCH3, -OCOCH2CH3, -CH2CH3, -Br.

Answer:  -Br < -CH2CH3 < -OCOCH2CH3 < -OCH3

Section:  18-12

MCAT:  17.2

 

89) Which of the following compounds reacts most rapidly with HNO3/H2SO4?

  1. A) toluene
  2. B) anisole
  3. C) nitrobenzene
  4. D) benzonitrile
  5. E) fluorobenzene

Answer:  B

Section:  18-12

MCAT:  17.2

 

90) List the following compounds in order of decreasing reactivity toward electrophilic aromatic substitution: toluene, benzene, fluorobenzene, nitrobenzene, phenol.

Answer:  phenol > toluene > benzene > fluorobenzene > nitrobenzene

Section:  18-12

MCAT:  17.2

 

91) In electrophilic aromatic substitution reactions, a chlorine substituent is

  1. A) a deactivator and a m-director
  2. B) a deactivator and an o,p-director
  3. C) an activator and a m-director
  4. D) an activator and an o,p-director
  5. E) none of the above

Answer:  B

Section:  18-12

MCAT:  17.2

 

92) Which of the following structures is the most important contributor to the resonance hybrid formed when toluene undergoes para nitration?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  A

Section:  18-15

MCAT:  2.3, 17.1

 

93) Which of the following structures is the most important contributor to the resonance hybrid formed when anisole undergoes o-bromination?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  D

Section:  18-15

MCAT:  2.3, 17.1

 

94) What is the major product of the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  C

Section:  18-13

 

95) Provide the major organic product(s) of the reaction below.

Answer:

Section:  18-13

 

96) Provide the major organic product(s) of the reaction below.

Answer:

Section:  18-13

 

97) Draw the four major resonance structures of the carbocation intermediate in the reaction of anisole with HNO3/H2SO4 to yield p-nitroanisole.

Answer:

Section:  18-13

MCAT:  17.1

 

98) Draw the three major resonance structures of the carbocation intermediate in the reaction of acetophenone with HNO3/H2SO4 to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

Answer:

Section:  18-13

MCAT:  2.3, 17.1

 

99) List the following compounds in order of decreasing basicity.

Answer:

Section:  8-10

MCAT:  19.3

 

100) List the following compounds in order of decreasing acidity.

Answer:

Section:  8-10

 

101) Which of the following monoalkylbenzenes undergo nitration in HNO3/H2SO4 to yield a product mixture with the highest ortho : para ratio?

  1. A) toluene
  2. B) ethylbenzene
  3. C) propylbenzene
  4. D) isopropylbenzene
  5. E) tert-butylbenzene

Answer:  A

Section:  18-14

 

 

102) What factors affect the ortho/para ratio in electrophilic aromatic substitution reactions?

Answer:  Based solely on probability, one would expect more of the ortho product because there are two ortho positions available to the incoming electrophile versus only on para position. However, the ortho position is sterically hindered relative to the para position. Consequently, the para product will be generated preferentially if either the substituent on the ring or the attacking electrophile is large.

Section:  18-14

MCAT:  17.2

GLO:  G2, G8

103) What is/are the product(s) from the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) no reaction

Answer:  E

Section:  18-15

 

104) Explain why nitrobenzene can be used as a solvent for Friedel-Crafts alkylation.

Answer:  Because of the deactivating nature of the NO2 group, it will not undergo a F.C. reaction.

Section:  18-15

GLO:  G2, G8

 

105) Explain why direct nitration of aniline yields, among other products, m-nitroaniline.

Answer:  In acidic media, the basic amino group forms a protonated ammonium ion which is a meta director.

Section:  18-15

 

106) Provide the structure of the major organic product of the following reaction.

Answer:  No reaction. The ring is too deactivated by the acyl substituent to undergo Friedel-Crafts alkylation.

Section:  18-15

GLO:  G2

107) What is the major organic product that results from the following sequence?

  1. A) styrene
  2. B) propylbenzene
  3. C) isopropylbenzene
  4. D) p-ethylaniline
  5. E) 2-phenyl-1-propanamine

Answer:  E

Section:  18-16

 

108) What is the major organic product of the reaction shown below?

 

Answer:

Section:  18-16

 

 

109) What is the best method for carrying out the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  B

Section:  18-16

110) Which is the best method for carrying out the following reaction?

  1. A) +COOH; HNO3/H2SO4
  2. B) CH3Cl/AlCl3; HNO3/H2SO4; KMnO4/H+, heat
  3. C) CH3Cl/AlCl3; KMnO4/H+, heat; HNO3/H2SO4
  4. D) HNO3/H2SO4; CH3Cl/AlCl3; KMnO4/H+, heat
  5. E) HNO3/H2SO4; +COOH

Answer:  C

Section:  18-16

GLO:  G2

 

 

111) Which is the best method for carrying out the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  E

Section:  18-16

GLO:  G2

 

112) Which of the following is the best method for preparing m-chloroaniline from benzene?

  1. A) NH3; Cl2/AlCl3
  2. B) Cl2/AlCl3; NH3
  3. C) Cl2/AlCl3; HNO3/H2SO4; Sn/HCl, HO-
  4. D) HNO3/H2SO4; Cl2/AlCl3; Sn/HCl, HO-
  5. E) HNO3/H2SO4; Sn/HCl; HO-; Cl2/AlCl3

Answer:  D

Section:  18-16

GLO:  G2

113) Provide the major organic products of the reaction shown below.

Answer:

Section:  18-16

 

114) What sequence of reagents can be used to accomplish the conversion shown below?

Answer:

  1. Mg, Et2O
  2. Oxirane
  3. H3O+
  4. PCC

Section:  18-16

GLO:  G2

 

 

115) Identify the product(s) for the following reaction. You may choose more than one answer.

  1. A)
  2. B)
  3. C)
  4. D)

 

  1. E)

Answer:  A, C

Section:  18-16

 

 

116) Identify the product(s) for the following reaction. You may choose more than one answer.

  1. A)
  2. B)
  3. C)
  4. D)

 

  1. E)
  2. F)

Answer:  D, F

Section:  18-13

 

117) Give the product(s) for each step of the following reaction.

Answer:

Section:  18-13

 

 

118) Give the best product(s) for the reaction.

  1. A)
  2. B)
  3. C)

 

  1. D)
  2. E) no reaction

Answer:  E

Section:  18-13

119) What sequence of reagents can be used to make m-bromobutylbenzene from benzene?

Answer:

Section:  18-16

 

120) What sequence of reagents can be used to make m-butylbenzoic acid from benzene?

Answer:

Section:  18-16

 

121) What sequence of reagents can be used to make p-butylbenzenesulfonic acid from benzene?

Answer:

Section:  18-16

 

122) What is the major product of the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  E

Section:  18-17

 

123) Provide a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene.

Answer:

1) HNO3, H2SO4

2) Br2, FeBr3

3) KMnO4, H+

Section:  18-16

GLO:  G2

 

124) What is the major product of the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  B

Section:  18-17

 

125) Provide the structure of the major mononitration product of the compound below.

Answer:

Section:  18-17

 

126) Provide the structure of the major mononitration product(s) of the compound below.

Answer:

Section:  18-17

 

127) Provide the structure of the major organic product of the following reaction.

Answer:

Section:  18-17

 

128) Give the product(s) for the following reaction.

Answer:

Section:  18-17

 

129) Give the product(s) for the following reaction.

Answer:

Section:  18-17

 

130) What is the best method for the preparation of p-chlorotoluene in high yield?

  1. A) start with benzene; methylate; chlorinate
  2. B) start with benzene; chlorinate; methylate
  3. C) start with toluene; chlorinate
  4. D) start with chlorobenzene; methylate
  5. E) start with p-aminotoluene; NaNO2/HCl, 0°C; CuCl

Answer:  E

Section:  18-16

GLO:  G2

 

131) What is the best method for the preparation of m-dibromobenzene from benzene?

  1. A) nitrate; Sn/HCl; NaNO2/HCl, 0°C; brominate twice
  2. B) nitrate; Sn/HCl; NaNO2/HCl, 0°C; brominate twice; H3PO2
  3. C) nitrate; Sn/HCl; NaNO2/HCl, 0°C; H3PO2; brominate twice
  4. D) nitrate; brominate; Sn/HCl; NaNO2/HCl, 0°C; CuBr
  5. E) brominate twice

Answer:  D

Section:  18-16

GLO:  G2

 

132) Which reagent is least likely to be used in the conversion shown?

  1. A) Na2Cr2O7
  2. B) HNO3
  3. C) Sn
  4. D) NaNO2
  5. E) HCl

Answer:  A

Section:  18-18

 

133) Provide the structure of the major organic product of the following reaction.

Answer:

Section:  18-18

 

134) What sequence of reagents can be used to accomplish the conversion shown below?

Answer:

  1. HNO3, H2SO4
  2. Br2, FeBr3
  3. Sn/HCl
  4. HO-
  5. NaNO2, HBr, 0 °C
  6. HBF4

Section:  18-18

135) Identify the best product for the reaction.

  1. A)
  2. B)
  3. C)
  4. D)
  5. E)

Answer:  A

Section:  18-18

 

136) Identify the best product for the reaction.

  1. A)
  2. B)
  3. C)
  4. D)
  5. E)

Answer:  A

Section:  18-18

 

137) Identify the best product for the reaction.

  1. A)
  2. B)
  3. C)
  4. D)
  5. E)

Answer:  C

Section:  18-18

138) What is one of the products of the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  C

Section:  18-19

 

139) What reagent is used to convert an arenediazonium salt into a fluoroarene?

  1. A) HBF4
  2. B) F2
  3. C) HF
  4. D) BF3
  5. E) B2F6

Answer:  A

Section:  18-18

140) Identify the best product for the reaction.

  1. A)
  2. B)
  3. C)

 

  1. D)
  2. E)

Answer:  C

Section:  18-20

 

 

141) Identify the major product for the reaction.

  1. A)
  2. B)
  3. C)

 

  1. D)
  2. E)

Answer:  C

Section:  18-20

142) Which of the following is most reactive toward nucleophilic aromatic substitution?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  D

Section:  18-21

GLO:  G2

 

143) Provide a detailed, stepwise mechanism for the following reaction.

Answer:

Section:  18-21

144) Draw the four major resonance structures of the intermediate which results when o-nitrochlorobenzene is treated with NaOH.

Answer:

Section:  18-21

 

145) Provide a series of synthetic steps by which p-bromoanisole can be prepared from benzene.

Answer:

1) Cl2, FeCl3

2) HNO3, H2SO4

3) NaOCH3

4) Sn, HCl

5) NaNO2, HCl, 0°C

6) CuBr

Section:  18-18, 18-16, 18-21

GLO:  G2

 

 

146) Identify the major product(s) for the reaction.

  1. A)
  2. B)
  3. C)
  4. D)

 

  1. E)

Answer:  C

Section:  18-21

 

 

147) Identify the major product(s) for the reaction.

  1. A)
  2. B)
  3. C)
  4. D)
  5. E)

Answer:  B, C

Section:  18-21

148) Which of the following undergoes solvolysis in water more rapidly?

Answer:

Section:  8-18

GLO:  G2

 

 

149) What is the major product from the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) I and II equally
  5. E) I and III equally

Answer:  A

Section:  18-13

150) What is the major product of the following reaction?

  1. A) I
  2. B) II
  3. C) III
  4. D) A and B equally
  5. E) A and C equally

Answer:  C

Section:  18-13

 

 

151) What is the name of the following compound?

Answer:  1,3-dinitronaphthalene

Section:  18-11

152) Provide the structure of the major organic product of the following reaction.

Answer:

Section:  18-13

 

 

153) Which of the following is the most acidic?

  1. A) I
  2. B) II
  3. C) III
  4. D) IV
  5. E) V

Answer:  E

Section:  8-18

154) Provide the major resonance structures of the ion which results when the most acidic hydrogen of cyclopentadiene is lost.

Answer:

Section:  8-18

MCAT:  15.2

 

155) Does cycloheptatriene have a higher or lower pKa than cyclopentadiene? Explain.

Answer:  Cycloheptatriene is a weaker acid than cyclopentadiene and thus has a higher pKa. Cyclopentadiene is more acidic because the cyclopentadienyl anion which results upon deprotonation is aromatic and thus more stable than the corresponding conjugate base of cycloheptatriene.

Section:  8-18

GLO:  G2, G8

 

 

156) Mark the most basic site in the molecule below with an asterisk.

Answer:

Section:  8-18

MCAT:  19.3

157) Which of the following cannot serve as a Lewis acid in electrophilic aromatic substitution?

  1. A) AlCl3
  2. B) FeCl3
  3. C) FeBr3
  4. D) BBr3
  5. E) NH3

Answer:  E

Section:  18-3

MCAT:  1.4

 

158) In nitration of benzene rings, what is the role of sulfuric acid?

  1. A) It protonates the benzene ring in the first step.
  2. B) It protonates the —OH group of the nitric acid.
  3. C) It protonates the nitrogen atom of the nitric acid.
  4. D) It deprotonates the —OH group of the nitric acid.
  5. E) none of the above

Answer:  B

Section:  18-4

 

159) Which of the following electrophilic aromatic substitution is reversible?

  1. A) halogenation
  2. B) nitration
  3. C) Friedel-Crafts Acylation
  4. D) Friedel-Crafts Alkylation
  5. E) sulfonation

Answer:  E

Section:  18-5

 

160) Sulfonation can be reversed

  1. A) upon treatment with Zn/HCl.
  2. B) upon treatment with chromic acid.
  3. C) upon treatment with NBS.
  4. D) in dilute acid at 100°C.
  5. E) upon treatment with NaBH4.

Answer:  D

Section:  18-5

 

161) Which of the following substituent on the benzene ring is a strong deactivator?

  1. A) -Cl
  2. B) -OCH3
  3. C) -COOH
  4. D) -NO2
  5. E) none of the above

Answer:  D

Section:  18-12

MCAT:  17.2

162) Which of the following substituent on the benzene ring is a strong deactivator?

  1. A) -+N(CH3)3
  2. B) -+NH(CH3)2
  3. C) -+NH2CH3
  4. D) -NO2
  5. E) all of the above

Answer:  E

Section:  18-12

MCAT:  17.2

 

163) Which of the following substituent on the benzene ring is a meta director?

  1. A) -Cl
  2. B) -COOH
  3. C) -CHO
  4. D) B and C
  5. E) all of the above

Answer:  D

Section:  18-12

MCAT:  17.2

 

 

164) In electrophilic aromatic substitution, a halogen substituent is considered as

  1. A) strongly activating.
  2. B) strongly deactivating.
  3. C) weakly activating.
  4. D) weakly deactivating.
  5. E) moderately activating.

Answer:  D

Section:  18-12

MCAT:  17.2

 

165) Fill in the empty boxes.

Answer:

Section:  18-16

GLO:  G2

166) Fill in the empty boxes.

Answer:

Section:  18-16

GLO:  G2

 

 

167) Fill in the empty boxes.

Answer:

Section:  18-16

GLO:  G2

168) Propose a synthesis of the following compound benzene.

Answer:

Section:  18-16

GLO:  G2

 

 

169) Propose a synthesis of the following compound benzene.

Answer:

Section:  18-16

GLO:  G2

170) Propose a synthesis of the following compound benzene.

Answer:

Section:  18-16

GLO:  G2

 

171) How would you convert benzene to 1,3,5-tribromobenzene?

Answer:

Section:  18-16

GLO:  G2

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