CHAPTER 22—REACTIONS OF BENZENE AND ITS DERIVATIVES MULTIPLE CHOICE
1. What is the the major organi organicc product product obtained obtained from from the followin following g reaction? reaction?
a. b. c. d.
1 2 3 4
ANS: B 2. What is the the major organi organicc product product obtained obtained from from the followin following g reaction? reaction?
a. b. c. d.
1 2 3 4
ANS: B . What is the the major organi organicc product product obtained obtained from from the followin following g reaction? reaction?
a. b. c. d.
1 2 3 4
ANS: ! ". What is the the major organi organicc product product obtained obtained from from the followin following g reaction? reaction?
a. b. c. d.
1 2 3 4
ANS: B #. What is the the major organi organicc product product obtained obtained from from the followin following g reaction? reaction?
a. b. c. d.
1 2 3 4
ANS: B
a. b. c. d.
1 2 3 4
ANS: ! ". What is the the major organi organicc product product obtained obtained from from the followin following g reaction? reaction?
a. b. c. d.
1 2 3 4
ANS: B #. What is the the major organi organicc product product obtained obtained from from the followin following g reaction? reaction?
a. b. c. d.
1 2 3 4
ANS: B
$. What is the electrophile electrophile in the the reaction of ben%ene with a mi&ture of nitric acid and sulfuric acid? a. '(N( b. N() c. N(2) d. ben%ene ANS: B *. What is the the electrophi electrophile le in the reaction reaction of ben%ene ben%ene with with acet+l acet+l chloride, chloride, -' -(-l, and Al-l ? ) a. -'-≡( b. -') c. -'-(2 d. ben%ene −
ANS: A . What is is the electro electrophil philee in the the reaction reaction of of ben%ene ben%ene with with tert /but+l /but+l chloride and Al-l ? ) a. -' b. -l) c. 0-'-) d. ben%ene ANS: . What What is is the the role role of of AlAl-ll in 3riedel -rafts ac+lations using acid chlorides? a. 4ewis ac acid b. electrophile c. base d. nucleophile ANS: A 15. 15. What What is is the the role role of of 3eBr 3eBr in electrophilic aromatic bromination of ben%ene using Br 2? a. nucleophile b. electrophile c. 4ewis ac acid d. base ANS: 11. 11. Which of the the following following undergoe undergoess the most rapid rapid nitration nitration upon upon treatment treatment with 'N( 'N( 6'2S("? a. toluene b. ben%ene c. brom romoben%ene d. nitro itrob ben%e en%en ne ANS: A 12. Which of the the following following undergoe undergoess the most rapid rapid brominatio bromination n upon treatment treatment with with Br 263eBr ? a. ben%ene b. nitroben%ene c. brom romoben%ene d. anisole ANS: !
1. Which of the following undergoes the most rapid sulfonation upon treatment with fuming sulfuric acid? a. ben%ene b. ben%oic acid c. ben%onitrile d. nitroben%ene ANS: A 1". Which of the following undergoes the most rapid ac+lation upon treatment with acet+l chloride and Al-l? a. ben%ene b. toluene c. chloroben%ene d. 1,"/dichloroben%ene ANS: B 1#. Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions? a. -l, -', -N b. Br, (', -(-' c. -l, (', -' d. -N, N(2, -(-' ANS: 1$. Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions? a. Br, -', N(2 b. -', N'2, Br c. -l, (-', -(-' d. N(2, -(-', -((' ANS: B 1*. Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions? a. -N, N(2, -(-' b. -', (-', -(-' c. -l, N'2, -' d. -', N', (-' ANS: A 1. Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions? a. -', (', Br b. -l, N'2, -N c. -(-', N(2, -((' d. N'2, -(-', (' ANS: -
1. Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions? a. -', (-', -(-' b. -l, -N, N(2 c. -l, N'2, -' d. -', N'2, (-' ANS: ! 25. Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions? a. Br, N'2, -' b. -', N'2, (-' c. (', -(-', -', d. Br, -N, N(2 ANS: B 21. Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions? a. -l, -N, N(2 b. -l, N'2, -' c. -', (-', -(-' d. -', N'2, (-' ANS: A 22. Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions? a. -l, (', -'2-' b. -', Br, -(-' c. -', N'2, (' d. -(-', N(2, Br ANS: ! 2. Which of the following substituents is ortho6para directing and deacti7ating in electrophilic aromatic substitution reactions? a. (' b. -l c. -' d. N(2 ANS: B 2". Which of the following substituents is ortho6para directing and deacti7ating in electrophilic aromatic substitution reactions? a. -(-' b. N' c. Br d. -'2-' ANS: -
2#. Which of the following reactions or reaction se8uences will not gi7e isoprop+lben%ene as the major product? a. treatment of ben%ene with isoprop+l alcohol and '3 b. treatment of ben%ene with 1/chloropropane and Al-l c. treatment of ben%ene with propano+l chloride and Al-l 9 followed b+ reaction with n0'g and '-l d. treatment of ben%ene with 1/propene and '3 ANS: 2$. Which of the following reactions or se8uences will pro7ide 1/prop+lben%ene as the major product? a. treatment of ben%ene with isoprop+l alcohol and '3 b. treatment of ben%ene with propano+l chloride and Al-l 9 followed b+ reaction with n0'g and '-l c. treatment of ben%ene with 1/chloropropane and Al-l d. treatment of ben%ene with 1/propene and '3 ANS: B 2*. Which of the following are 7alid resonance structures of the electophile in7ol7ed in 3riedel/-rafts ac+lation of ben%ene upon treatment with -' -(-l and Al-l ?
a. b. c. d.
1 2 3 4
ANS: A 2. Which of the following is the structure of the comple& of Br 2 with 3eBr in7ol7ed in the electrophilic bromination of ben%ene?
a. b. c. d.
1 2 3 4
ANS: !
2. Which of the following sets of reagents does not result in al;+lation of ben%ene? a. tert /but+l chloride ) Al-l b. tert- but+l alcohol ) '<(" c. meth+lpropene ) '3 d. meth+lpropane ) '2S(" ANS: ! 5. Wh+ does nitroben%ene fail to undergo 3ieldel/-rafts al;+lation with tert /but+l chloride and Al-l ? a. nitroben%ene reacts with Al-l b. nitroben%ene is a poor nucleophile c. the nitro group is a strong electron donating group d. the tert /but+l cation is a poor electrophile ANS: B 1. Wh+ does anisole undergo bromination with Br 2 in the absence of 3eBr whereas bromination of ben%ene re8uires the presence of 3eBr ? a. anisole is a better nucleophile than ben%ene b. the metho&+ group of anisole is an inducti7e electron withdrawing substituent c. Br2 is a good nucleophile d. the reaction is accelerated b+ light ANS: A 2. What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: B
. What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: ". What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: A #. What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: B $. What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: B *. What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: !
. What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: ! . What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: !
"5. What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: B "1. What is the major organic product obtained from the following reaction?
a. b. c. d.
1 2 3 4
ANS: !
"2. What is the major organic product obtained from the following se8uence of reactions?
a. b. c. d.
1 2 3 4
ANS: A ". What is the major organic product obtained from the following se8uence of reactions?
a. b. c. d.
1 2 3 4
ANS: -
"". What is the major organic product obtained from the following se8uence of reactions?
a. b. c. d.
1 2 3 4
ANS: A "#. What is the major organic product obtained from the following se8uence of reactions?
a. b. c. d.
1 2 3 4
ANS: -
"$. What is the major organic product obtained from the following se8uence of reactions?
a. b. c. d.
1 2 3 4
ANS: ! "*. What is the major organic product obtained from the following se8uence of reactions?
a. b. c. d.
1 2 3 4
ANS: A
". Which of the following cannot be prepared from ben%ene in two s+nthetic steps?
a. b. c. d.
1 2 3 4
ANS: ! ". Which of the following cannot be prepared from ben%ene in two s+nthetic steps?
a. b. c. d.
1 2 3 4
ANS: A
#5. Which of the following is the reacti7e intermediate in the nucleophilic substitution of "/bromo/1/ nitroben%ene with sodium h+dro&ide?
a. b. c. d.
1 2 3 4
ANS: A #1. Which of the following is the reacti7e intermediate in the nucleophilic substitution of "/bromo/1/ toluene with sodium amide?
a. b. c. d.
1 2 3 4
ANS: !
#2. Which of the following is the reacti7e intermediate formed in the electrophilic bromination of toluene with Br 2, 3eBr ?
a. b. c. d.
1 2 3 4
ANS: #. Which of the following is the reacti7e intermediate formed in the electrophilic nitration of nitroben%ene with 'N( and '2S("?
a. b. c. d.
1 2 3 4
ANS: B
#". Which of the following is the reacti7e intermediate formed in the electrophilic 3riedel/-rafts ac+lation of toluene with -' -(-l and Al-l?
a. b. c. d.
1 2 3 4
ANS: ! ##. Which of the following compounds undergoes the most rapid nucleophilic substitution with h+dro&ide ion?
a. b. c. d.
1 2 3 4
ANS: !
#$. Which of the following compounds undergoes the most rapid nucleophilic substitution with h+dro&ide ion?
a. b. c. d.
1 2 3 4
ANS: #*. Which of the following chloroben%enes produces a single isomer upon treatment with NaN' 2?
a. b. c. d.
1 2 3 4
ANS: ! #. Which of the following chloroben%enes does not undergo nucleophilic aromatic substitution upon treatment with NaN' 2?
a. b. c. d.
1 2 3 4
ANS: A #. Which mechanism accounts for the reaction of "/bromo/1/nitroben%ene with sodium h+dro&ide to form "/nitrophenol? a. Bimolecular nucleophilic substitution 0S N2 b. Nucleophilic aromatic substitution b+ elimination/addition c. Nucleophilic aromatic substitution b+ addition/elimination d. =lectrophilic aromatic substitution ANS: $5. Which mechanism accounts for the reaction of chloroben%ene with acet+l chloride and Al-l to form "/chloroacetophenone? a. Bimolecular nucleophilic substitution 0S N2 b. Nucleophilic aromatic substitution b+ elimination/addition c. Nucleophilic aromatic substitution b+ addition/elimination d. =lectrophilic aromatic substitution ANS: ! $1. Which mechanism accounts for the reaction of ben%+l chloride with sodium c+anide to form c+anometh+lben%ene 0phen+lacetonitrile, eisenheimer comple& b. ben%+ne c. c+clohe&adien+l cation d. ben%+l radical ANS: -
$". What t+pe of intermediate is formed in the reaction between bromoben%ene and sodium amide to gi7e aniline? a. >eisenheimer comple& b. ben%+ne c. c+clohe&adien+l cation d. ben%+l radical ANS: B $#. What t+pe of intermediate is formed in upon irradiation of a mi&ture of toluene and chlorine to gi7e ben%+l chloride? a. >eisenheimer comple& b. ben%+ne c. c+clohe&adien+l cation d. ben%+l radical ANS: ! $. Which of the following is not true about ben%+nes? a. he+ are planar b. he+ are formed upon deh+drohalogenation of ar+l halides c. he+ are aromatic d. he+ are intermediates in nucleophilic aromatic substitution reaction which ta;e place b+ an addition/elimination mechanism ANS: !
$.
A =
B
=
- =
! =
=
none of these ANS: A
*5 What major product would +ou e&pect from the following reaction? ('
'N( '2S("
A ('
N(2
B ('
(2 N
- (' N(2
! ('
N(2
= ('
N(2 A
ANS: A
?
71. Predict the major organic product of the following reaction.
( N(2 -'( N(2 A) ( Br
N(2
-'( N(2
B) Br
( N(2
-'( N(2
C) (
Br N(2
-'( N(2
D)
Br
(' N(2
-'( N(2
E)
Br 2 6 3eBr
?
( N(2 Br
-'( N(2
ANS A
PROBLEM
1. What is the major organic product obtained from the following reaction?
ANS:
2. What is the major organic product obtained from the following reaction?
ANS:
. What is the major organic product obtained from the following reaction?
ANS:
". What is the major organic product obtained from the following reaction?
ANS:
#. What is the major organic product obtained from the following reaction?
ANS:
$. What is the major organic product obtained from the following reaction?
ANS:
*. What is the major organic product obtained from the following se8uence of reactions 0if a reaction is li;el+ to gi7e +ou a mi&ture of ortho and para disubstituted compounds +ou should assume that the + can be separated9 continue the s+nthesis with either one)?
ANS:
. What is the major organic product obtained from the following reaction 0if a reaction is li;el+ to gi7e +ou a mi&ture of ortho and para disubstituted compounds +ou should assume that the+ can be separated9 continue the s+nthesis with either one)?
ANS:
. What is the major organic product obtained from the following se8uence of reactions 0if a reaction is li;el+ to gi7e +ou a mi&ture of ortho and para disubstituted compounds +ou should assume that the + can be separated9 continue the s+nthesis with either one)?
ANS:
15. What is the major organic product obtained from the following reaction 0assume that mi&tures of ortho and para disubstituted compounds can be separated9 continue the s+nthesis with either one)?
ANS:
or ortho isomer
11. What is the major organic product obtained from the following reaction 0assume that mi&tures of ortho and para disubstituted compounds can be separated9 continue the s+nthesis with either one)?
ANS:
12.
ANS:
1.
ANS:
1".
ANS:
1#.
ANS:
1$