CHEM 334 Study Guide - Spring 2019, Comprehensive Final Exam Notes - Acid, Carbocation, Sodium Hydroxide

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8 May 2019
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Practice Problems for Chapter 17: Reactions of Aromatic Compounds
1) Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene
with the generic electrophile E+.
3) Under what reaction conditions does the electrophilic chlorination of aromatic compounds usually
occur?
A) Cl2, AlCl3
B) Cl2, H2O
C) Cl2, CCl4
D) NaCl, H2O
E) NaCl, CH3OH
4) In the bromination of benzene using Br2 and FeBr3, is the intermediate carbocation aromatic?
Explain.
5) In electrophilic aromatic substitution reactions a bromine substituent:
A) is a deactivator and a m-director.
B) is a deactivator and an o,p-director.
C) is an activator and a m-director.
D) is an activator and an o,p-director.
E) none of the above
6) Which of the following is the best choice of reagents to effect the electrophilic iodination of an
aromatic ring?
A) KI, acetone
B) I2, CH3CN
C) KI, HNO3
D) I2, HNO3
E) none of the above
TEEF TEEHEE FI
CHAN detail
Mr If
nonaromatic
sp3
OACTIVATORS
HALOGENS.co
pdirectors deactivating
resonant
or
inductive WPdirectors
oNk R
HClt
NO
O
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9) 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.
10) Which of the following species is attacked by benzene in the electrophilic nitration reaction?
A) HNO3
B) NO2+
C) NO2
D) NO+
E) N3-
12) Provide the necessary reagents to accomplish the following transformation.
13) Which of the following is the strongest activating group in electrophilic aromatic substitution
reactions?
A) -CH2CH3
B) -OCH3
C) -CO2CH3
D) -NO2
E) -N(CH3)2
BrBr tFeBrs BrBro Bras
µr trEe
BB IIFeBr5 4HbrFeb
I040
off 2112504
For zBrztFeBr
Oortho
D
903
meta para
step1block
para
reactive
knee
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