Organic Chemistry
Carey/Giuliano
10th edition
Chapter 13
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Question 1
Arrange the compounds below in order of
decreasing rate of chlorination.
A) 1>2>3
B) 2>3>1
C) 3>2>1
D) 1>3>2
Question 2
Which compound will react faster with Br 2 in
acetic acid?
A) B)
C) D)
Question 3
Which compound will add a nitro group to the
meta position?
A) B)
C) D)
Question 4
Which positions are activated for chlorination
on the compound shown below?
A) 2 and 3
B) 1 and 3
C) 2 and 4
D) 1 and 4
Question 5
Which combination of reactants will yield n-
propylbenzene as the major product when
reacted with benzene?
A) CH3CH2C(=O)H, AlCl3
B) CH3CH2CH2Cl, AlCl3
C) CH3CH2C(=O)Cl, AlCl3 followed by
Zn(Hg), HCl
D) CH3CH2CH3, AlCl3
Question 6
A Friedel-Craft acylation cannot be performed
on which compound?
A) 3 only B) 4 only
C) 1 and 2 D) 3 and 4
Question 7
The carbocation formed in the first step of the
electrophilic aromatic substitution
mechanism is known as:
A) arenium ion
B) -complex
C) cyclohexadienyl cation
D) all of the above
Question 8
Which compound undergoes electrophilic
aromatic substitution with (CH3)3CCl and AlCl3
at the slowest rate (or not at all)?
A) B)
C) D)
Question 9
Which of the following statements concerning
nucleophilic aromatic substitution in
1,2,3,4,5,6-hexafluorobenzene is true?
A) 1,2,3,4,5,6-hexafluorobenzene is less
reactive than fluorobenzene.
B) 1,2,3,4,5,6-hexafluorobenzene is more
reactive than 1,2,3,4,5,6-hexachlorobenzene.
C) The reaction takes place in a single
elementary step.
D) The carbon-fluorine bond breaks in the rate-
determining step.
Question 10
Which substituent is classified as deactivating
and ortho-para directing in electrophilic
aromatic substitution?
A) -Cl
B) -CH=O
C) -NH2
D) -SCH3
Question 11
Which reactants combine to
give the species shown at
the right as a reactive
intermediate?
A) Benzene, isopropyl bromide, and HBr
B) Bromobenzene, isopropyl chloride, and AlCl3
C) Isopropylbenzene, Br2, FeBr3
D) Isopropylbenzene, light, and heat
Question 12
Which of the following is the most reasonable way to
begin an effective synthesis of the
compound shown?
A) Treat benzene with isopropyl chloride and AlCl3.
B) Treat chlorobenzene with propene and AlCl3.
C) Treat benzene with 2-chloropropene and AlCl3.
D) Treat benzene with 3-chloropropene and AlCl3.
Question 13
Which phenol is most acidic?
A) phenol
B) 2-methyl-6-nitrophenol
C) 3-methyl-5-nitrophenol
D) 2,6-dimethyl-3-nitrophenol
Question 14
Which of the following is the most activating
substituent in electrophilic aromatic
substitution?
A) -CN
B) -CO2CH3
C) -NHC(=O)CH3
D) -SO3H
Question 15
Which compound will react faster with NaOCH3
in methanol (50oC)?
A) B)
C) D)
Question 16
Which organic product would you expect to isolate
from the reaction of p-fluoronitrobenzene with
potassium methoxide?
A) B)
C) D)
Question 17
Which of the structures below is the most stable
resonance structure for the reaction of p-
fluoronitrobenzene with sodium methoxide?
A) 1 only B) 2 only
C) 3 only D) 1 and 2
Question 18
What is the product of the reaction of 2-
chloropyridine with KOCH3 (shown below)?
A) B)
C) D)
Question 19
Which is the product of the reaction of p-
chloronitrobenzene with NH3?
A) B)
C) D)
Question 20
What is the product of the synthetic sequence
shown at the right?
A) B)
C) D)
Question 21
What product will be isolated when o-
bromotoluene is treated with NaNH2 in NH3?
A) B)
C) D) Both A and B
Question 22
What combination of reactants
will give the species shown
as a reactive intermediate?
A) 1-bromo-4-nitrobenzene and NaOH
B) bromobenzene and HONO2
C) 4-nitrophenol with HBr
D) 4-nitrophenol, Br2 and FeBr3
Question 23
The reaction shown below most likely involves
which of the following aromatic substitution
mechanisms?
A) addition-elimination
B) electrophilic substitution
C) elimination-addition
D) both A and C
Question 24
Which of the following compounds give a
single benzyne intermediate on reaction with
sodium amide?
A) 1 only B) 1 and 3
C) 3 only D) 1 and 2
Question 25
Which of the following compounds is the least
reactive toward nucleophilic aromatic
substitution?
A) 1-chloro-4-nitrobenzene
B) 1-iodo-2-nitrobenzene
C) 1-fluoro-4-nitrobenzene
D) 1-bromo-3-nitrobenzene
Question 26
Identify the rate law for the addition-elimination
mechanism of nucleophilic aromatic
substitution.
A) Rate = [aryl halide]
B) Rate = [aryl halide][nucleophile]
C) Rate = [aryl halide][nucleophile]2
D) Rate = [nucleophile]
Question 27
Which of the following statements is true
regarding nucleophilic aromatic substitution
reactions (SNAr)?
A) A nitro (NO2) group strongly activates
the ring toward SNAr.
B) The SNAr reaction is facilitated when
electrons flow from the attacking
species to the aromatic ring.
C) The SNAr follows second-order kinetics.
D) All of the statements above are true.
Question 28
How many different methylaniline isomers will
be formed in the reaction of p-chlorotoluene
with KNH2 in NH3?
A) 1
B) 2
C) 3
D) 4
Question 29
How many different methylaniline isomers will
be formed in the reaction of m-chlorotoluene
with KNH2 in NH3?
A) 1
B) 2
C) 3
D) 4
Question 30
Arrange the aryl halides in order decreasing
reactivity with magnesium.
A) ArF > ArCl > ArBr > ArI
B) ArF > ArCl > ArI > ArBr
C) ArI > ArBr > ArCl > ArF
D) ArF > ArBr > ArCl > ArI
Question 31
Which one of the following compounds has the
greatest dipole moment ()?
A) Chlorohexane
B) Chlorobenzene
C) Benzene
D) 1,3-Pentadiene
Question 32
How many signals would be observed in the
1
H-NMR of the product isolated from the
reaction of p-fluoronitrobenzene with
potassium methoxide in methanol?
A) 2
B) 3
C) 4
D) 5
Question 33
Which of the following aromatic compounds will
not react with KNH2 via the
elimination-addition mechanism?
A) Chlorobenzene
B) 1-ethyl-4-iodobenzene
C) 2-Bromotoluene
D) Benzylbromide
Question 34
What type of nucleophilic aromatic substitution is
the reaction of m-dinitrophenol with NaOH
(shown)?
A) SN2
B) elimination-addition
C) addition-elimination
D) The reaction is an electrophilic aromatic
substitution.
Answer Key – Chapter 13
1. A 11. C 21. D 31. A
2. A 12. A 22. A 32. B
3. D 13. B 23. C 33. D
4. C 14. C 24. B 34. C
5. C 15. D 25. D
6. A 16. C 26. B
7. D 17. C 27. D
8. B 18. B 28. B
9. B 19. B
29. C
10. A 20. C
30. C