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Chapter13 (11th Ed) Practice Problems

This document contains 20 multiple choice questions about organic chemistry from Chapter 12. The questions cover topics like electrophilic aromatic substitution, rates of reactions, functional group effects on reactivity, and synthesis reactions.

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16 views

Chapter13 (11th Ed) Practice Problems

This document contains 20 multiple choice questions about organic chemistry from Chapter 12. The questions cover topics like electrophilic aromatic substitution, rates of reactions, functional group effects on reactivity, and synthesis reactions.

Uploaded by

lianahajj
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Organic Chemistry

Francis A. Carey
7th edition

Chapter 12

Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
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 Br2 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

Which set of reagents is best to chlorinate


benzene?
A) HCl, peroxides
B) Cl2, hv
C) Cl2, CCl4
D) Cl2, FeCl3
Question 7

Which set of reagents would convert benzene


into acetophenone (shown) in the highest
yield?

A) B)

C) D)
Question 8
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 9
Which of the following statements is false?
A) All activating groups are ortho, para
directors.
B) Halogen substituents are highly
deactivating but are ortho, para directing.
C) Strongly deactivating substances are meta
directors.
D) Some of the most powerful activating
substances are those with an oxygen
directly attached to the ring.
Question 10

Which group deactivates the ring toward


electrophilic aromatic substitution?
A) -OCH3
B) -CH=CH2
C) -CH3
D) -CF3
Question 11

The carbocation formed in the first step of the


electrophilic aromatic substitution
mechanism is known as:
A) arenium ion
B) s-complex
C) cyclohexadienyl cation
D) all of the above
Question 12

Which compound undergoes electrophilic


aromatic substitution with (CH3)3CCl and AlCl3
at the slowest rate (or not at all)?

A) B)

C) D)
Question 13
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 14
Which step is incorrect in respect to its major
organic product? Give the letter
corresponding to the first incorrect step.

A) Step A B) Step B
C) Step C D) Step D
Question 15

Which substituent is classified as deactivating


and ortho-para directing in electrophilic
aromatic substitution?
A) -Cl
B) -CH=O
C) -NH2
D) -SCH3
Question 16

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 17
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 18

Which phenol is most acidic?


A) phenol
B) 2-methyl-6-nitrophenol
C) 3-methyl-5-nitrophenol
D) 2,6-dimethyl-3-nitrophenol
Question 19

Which is the most likely candidate for


substituent X based on the partial rate
factors for nitration given beside the
structural formula?
A) -OCH3
B) -CH=O
C) -SO3H
D) -Br
Question 20

Which of the following is the most activating


substituent in electrophilic aromatic
substitution?
A) -CN
B) -CO2CH3
C) -NHC(=O)CH3
D) -SO3H
Answer Key – Chapter 12
1. A 11. D
2. A 12. B
3. D 13. B
4. C 14. C
5. C 15. A
6. D 16. C
7. C 17. A
8. A 18. B
9. B 19. D
10. D 20. C

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