Organic Chemistry, 7e (Bruice)

Chapter 19 Reactions of Benzene and Substituted Benzenes

1) Provide the structure of anisole.
Answer:
Section: 19-1
2) Provide the structure of benzenesulfonic acid.
Answer:
Section: 19-1
3) Provide the structure of dibenzyl ether.
Answer:
Section: 19-1
1
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%) )a*e the followin" co*!ound.
A) sec-he+ylbenzene
,) 3-!henylhe+ane
) 2-!henylhe+ane
-) tert-he+ylbenzene
&) isohe+ylbenzene
Answer:
Section: 19-1
.) -raw benzyl bro*ide.
Answer:
Section: 19-1
/) 0hat is the structure of styrene1
A) (
,) ((
) (((
-) (2
&) 2
Answer: A
Section: 19-1
2
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3) 0hich of the followin" is not a correct state*ent about the electro!hilic substitution
*echanis* of benzene1
A) ,enzene functions as a nucleo!hile.
,) 4or*ation of a carbocation inter*ediate is the rate-deter*inin" ste!.
) 5he carbocation inter*ediate contains an s!
3
hybridized carbon in the rin".
-) 5he addition !roduct is a fre6uent *inor !roduct.
&) Aro*aticity is re"ained by loss of 7
8
.
Answer: -
Section: 19-2
9) 0hy does benzene under"o electro!hilic substitution rather than electro!hilic addition1
Answer: 0hen benzene under"oes electro!hilic substitution' the !roduct retains the stability
associated with an aro*atic syste*. 5his stability is lost in electro!hilic addition because the
!roduct is not aro*atic.
Section: 19-2
9) 0hich of the followin" is *ost li:ely to be the first ste! in the "eneral *echanis* for
electro!hilic substitution reactions1
A) (
,) ((
) (((
-) (2
&) 2
Answer: ,
Section: 19-3
1$) Provide the *a;or resonance structures of the inter*ediate si"*a co*!le+ in the reaction of
benzene with the "eneric electro!hile &
8
.
Answer:
Section: 19-3
3
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11) (n the bro*ination of benzene usin" ,r
2
and 4e,r
3
' is the inter*ediate carbocation
aro*atic1 &+!lain.
Answer: )o' the carbocation is not aro*atic since the rin" contains an s!
3
center.
Section: 19-3
12) 0hich ste! in the "eneral *echanis* for electro!hilic aro*atic substitution is rate-
deter*inin"1 &+!lain.
Answer: 5he first ste! involves addition of the electro!hile to benzene to yield a nonaro*atic
cationic inter*ediate. 5he second ste! involves the loss of 78 fro* this cationic inter*ediate to
yield an aro*atic !roduct. 5he rate-deter*inin" or slow ste! is the one in which the aro*atic
rea"ent is converted into a *uch less stable nonaro*atic cation.
Section: 19-3
13) 0hich of the followin" is one of the resonance contributors of the inter*ediate !roduced in a
4riedel-rafts al:ylation of benzene1
A) (
,) ((
) (((
-) (2
&) 2
Answer: A
Section: 19-3
%
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1%) 0hich of the followin" is the first ste! in the *echanis* of bro*ination1
A) (
,) ((
) (((
-) (2
&) 2
Answer:
Section: 19-%
1.) 0hat !ur!ose does 4el
3
serve in the electro!hilic aro*atic substitution reaction between
chlorine and benzene1
A) (t serves as a radical initiator to !roduce the chlorine radical needed to !ro!a"ate the chain
reaction.
,) (t functions by destabilizin" the carbocationic inter*ediate and thereby increases the rate of
7
8
loss.
) (t serves as a <ewis base catalyst by reactin" with l
2
to "enerate chloride ions.
-) (t functions by destabilizin" the benzene throu"h for*ation of a =-co*!le+.
&) (t serves as a <ewis acid catalyst by reactin" with the l
2
and thereby activates it toward
attac: by benzene>s = electrons.
Answer: &
Section: 19-%
1/) Provide a detailed' ste!wise *echanis* for the reaction of benzene with ,r
2
and 4e,r
3
.
?a:e sure to include the activatin" reaction between ,r
2
and 4e,r
3
in your *echanis*.
Answer:
Section: 19-%
.
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13) ,ro*ination of benzene re6uires a <ewis acid catalyst while bro*ination of cyclohe+ene
does not. &+!lain this difference in reactivity.
Answer: An al:ene is a better nucleo!hile than benzene' and thus the ,r-,r bond does not have
to be wea:ened to for* a better electro!hile before reaction.
Section: 19-%
19) @ive the best !roduct for the followin" reaction.
Answer:
Section: 19-%
19) 0hich of the followin" is the electro!hile that attac:s the aro*atic rin" durin" nitration1
A) )A
2
,) 7)A
3
) 7)A
3
-
-) )A
2
8
&) )A
2
-
Answer: -
Section: 19-.
2$) 0hat s!ecific electro!hile is attac:ed by benzene when it under"oes nitration1
A) 7)A
3
,) )A
3
) )A
-) )A
2
&) )A
2
8
Answer: &
Section: 19-.
/
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21) (dentify the best !roduct for the followin" reaction.
A)
,)
)
-)
&)
Answer: A
Section: 19-.
3
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22) Predict the *a;or or"anic !roduct of the followin" reaction.
A) (
,) ((
) (((
-) (2
&) 2
Answer: -
Section: 19-/
23) 0hich of the followin" is the electro!hile that attac:s the aro*atic rin" durin" sulfonation1
A) 7SA
3
8
,) SA
2
8
) 7SA
3
-
-) 7
2
SA
%
&) 7SA
%
-
Answer: A
Section: 19-/
2%) )a*e the *a;or or"anic !roduct which results when %-ethylbenzenesulfonic acid is heated in
a6ueous acid.
Answer: ethylbenzene
Section: 19-/
2.) 0hat is the !rinci!le of *icrosco!ic reversibility1
Answer: 5his !rinci!le states that the *echanis* of a reaction in the reverse direction *ust
retrace each ste! of the *echanis* in the forward direction in *icrosco!ic detail. ,oth the
forward and reverse reactions *ust have the sa*e inter*ediates and transition states.
Section: 19-/
9
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2/) (dentify the best !roduct for the followin" reaction.
A)
,)
)
-)
&)
Answer: A
Section: 19-/
23) 0hich of the followin" is not a correct state*ent concernin" the 4riedel-rafts acylation of
benzene1
A) An al:yl "rou! substitutes for a hydro"en.
,) 5he benzene rin" attac:s an acyliu* ion.
) 5he acyliu* ion is resonance stabilized.
-) 5he acyliu* ion is often !roduced fro* an acyl chloride.
&) ?ore than one e6uivalent of <ewis acid *ust be used.
Answer: A
Section: 19-3
9
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29) 0hich of the followin" is the electro!hile that attac:s the aro*atic rin" durin" 4riedel-rafts
acylation1
A)
,)
)
-)
&) All
3
Answer: ,
Section: 19-3
29) 0hy *ust 4riedel-rafts acylation reactions be run with *ore than a sin"le e6uivalent of
All
3
1
Answer: 5hese reactions *ust be run with *ore than one e6uivalent of All
3
because the
!roduct of the reaction contains a carbonyl "rou! that can co*!le+ with All
3
.
Section: 19-3
3$) Provide the *a;or or"anic !roduct of the reaction shown below.
Answer:
Section: 19-3
1$
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31) (dentify the best !roduct for the followin" reaction.
A)
,)
)
-)
&)
Answer: &
Section: 19-3
11
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32) (dentify the best !roduct for the followin" reaction.
A)
,)
)
-)
&)
Answer: -
Section: 19-3
12
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33) 0hat is the *a;or !roduct of the followin" 4riedel-rafts al:ylation1
A) (
,) ((
) (((
-) (2
&) 2
Answer:
Section: 19-9
3%) 0hat is the *a;or or"anic !roduct of the reaction between benzene and isobutyl chloride in
the !resence of All
3
1
A) tert-butylbenzene
,) isobutylbenzene
) n-butylbenzene
-) chlorobenzene
&) sec-butylbenzene
Answer: A
Section: 19-9
13
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3.) Provide the *a;or or"anic !roduct of the reaction shown below.
Answer:
Section: 19-9
3/) Provide the *a;or or"anic !roduct of the reaction shown below.
Answer:
Section: 19-9
33) Provide the *a;or or"anic !roduct of the reaction shown below.
Answer:
Section: 19-9
1%
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39) Provide the structure of the *a;or or"anic !roduct of the followin" reaction.
Answer:
Section: 19-9
39) Provide the *a;or or"anic !roduct of the followin".
Answer:
Section: 19-9
1.
o!yri"ht # 2$1% Pearson &ducation' (nc.
%$) (dentify the *a;or !roduct for the followin" reaction.
A)
,)
)
-)
&)
Answer: &
Section: 19-9
%1) 0hat is the *a;or or"anic !roduct that results when benzene is treated with 1-chlorobutane
and All
3
1
A) ethylbenzene
,) isobutylbenzene
) butylbenzene
-) sec-butylbenzene
&) isobutylbenzene
Answer: -
Section: 19-9
1/
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%2) Provide the *a;or or"anic !roduct of the followin".
Answer:
Section: 19-9
%3) 0hat is the *a;or or"anic !roduct of the reaction shown below1
Answer:
Section: 19-9
13
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%%) (dentify the conditionBs) that will not wor: for the followin" reaction.
A)
,)
)
-) 7
3
7
2
7
2
l 8 All
3
&) 7
3
7
2
7
2
A7' 7
2
SA
%
Answer: -' &
Section: 19-9
%.) 0hat is the *a;or or"anic !roduct of the reaction shown below1
Answer:
Section: 19-1$
19
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%/) 0hat is the *a;or or"anic !roduct of the reaction shown below1
Answer:
Section: 19-1$
%3) (dentify the best !roduct for the followin" reaction.
A)
8 <i,r
,)
)
-)
&)
Answer: A
Section: 19-1$
19
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%9) @ive the or"anic !roducts fro* the followin" reaction.
Answer:
Section: 19-1$
%9) @ive the or"anic !roducts fro* the followin" reaction.
Answer:
Section: 19-1$
.$) 0hat is the *a;or !roduct of the followin" reaction1
A) (
,) ((
) (((
-) (2
&) 2
Answer: -
Section: 19-12
2$
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.1) 0hat is the *a;or !roduct of the followin" reaction1
A) (
,) ((
) (((
-) (2
&) 2
Answer: A
Section: 19-12
.2) 0hat is the *a;or !roduct of the followin" reaction1
A) (
,) ((
) (((
-) (2
&) 2
Answer: &
Section: 19-12
21
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.3) ,enzene can be reduced to cyclohe+ane when it is treated with hydro"en in the !resence of a
nic:el catalyst under conditions of hi"h te*!erature and !ressure. Predict the si"ns of C7D and
CSD for this !rocess.
A) C7D E $' CSD E $
,) C7D E $' CSD F $
) C7D E $' CSD G $
-) C7D F $' CSD E $
&) C7D F $' CSD F $
Answer: &
Section: 19-12
.%) 0hich of the followin" fails to !roduce benzoic acid when heated in the !resence of acidic
sodiu* dichro*ate1
A) 1-!henylethanol
,) 2-!henylethanol
) 2-!henylhe!tane
-) 2-*ethyl-2-!henylhe!tane
&) 1-!henylhe!tanol
Answer: -
Section: 19-12
..) Provide the structure of the *a;or or"anic !roduct of the followin" reaction se6uence.
Answer:
Section: 19-12
22
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./) Provide the structure of the *a;or or"anic !roduct of the followin" reaction.
Answer:
Section: 19-12
23
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.3) (dentify the !roductBs) for the followin" reaction.
A)
,)
)
-)
&)
Answer: -
Section: 19-12
2%
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.9) (dentify the best !roduct for the followin" reaction.
A)
,)
)
-)
&)
Answer:
Section: 19-12
2.
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.9) (dentify the best !roduct for the followin" reaction.
A)
,)
)
-)
&)
Answer: ,
Section: 19-12
/$) (dentify the reactionBs) below that "ive benzoic acid as a !roduct.
A) 1-!henylethanol 8 *an"anese dio+ide 8 heat
,) 1-!henylethanol 8 sodiu* dichro*ate 8 acid 8 heat
) tert-butylbenzene 8 sodiu* dichro*ate 8 acid 8 heat
-) ethylbenzene 8 sodiu* dichro*ate 8 acid 8 heat
&) !henyl*ethanol 8 *an"anese dio+ide 8 heat
Answer: ,' -
Section: 19-12
2/
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/1) (dentify the best !roduct for the followin" reaction.
A)
,)
)
-)
&)
Answer:
Section: 19-12
/2) @ive the best !roduct for the followin" reaction.
Answer:
Section: 19-12
23
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/3) @ive the best !roduct for the followin" reaction.
Answer:
Section: 19-12
/%) 0hat is the structure of !henol1
A) (
,) ((
) (((
-) (2
&) 2
Answer: -
Section: 19-13
/.) 0hat is the na*e of the followin" co*!ound1
A) m-bro*o*ethylbenzene
,) m-bro*otoluene
) 3-bro*otoluene
-) A and ,
&) , and
Answer: &
Section: 19-13
29
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//) 0hat is the structure of 3-!henyl!entane1
A) (
,) ((
) (((
-) (2
&) 2
Answer: &
Section: 19-13
/3) 5he na*e 2'%'/-tribro*obenzene is incorrect. 0hich of the followin" is the correct na*e1
A) tribro*obenzene
,) m'm-dibro*obro*obenzene
) 3'.-dibro*obro*obenzene
-) 1'3'.-tribro*obenzene
&) m'm'm-tribro*obenzene
Answer: -
Section: 19-13
29
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/9) 0hat is the na*e of the followin" co*!ound1
A) p-dichlorobenzene
,) 1'%-dichlorobenzene
) !henyldichloride
-) A and ,
&) , and
Answer: -
Section: 19-13
/9) 0hat is the structure of p-toluidine1
A) (
,) ((
) (((
-) (2
&) 2
Answer:
Section: 19-13
3$) 0hat is the na*e of the followin" co*!ound1
A) o-nitro-m-bro*otoluene
,) 3-bro*o-/-nitrotoluene
) m-bro*o-o-nitrotoluene
-) .-bro*o-2-nitrotoluene
&) 2-nitro-.-bro*otoluene
Answer: -
Section: 19-13
3$
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31) 0hat is the !ro!er na*e of the co*!ound below1
A) 1-!heno+yethane
,) ethyl !henyl ether
) m-butylhydro+ybenzene
-) o-butylhydro+ybenzene
&) m-butyl!henol
Answer: &
Section: 19-13
32) 7ow *any si"nals does one e+!ect in the !roton decou!led
13
)?H s!ectru* of o-
+ylene1
A) 9
,) /
) %
-) 3
&) 2
Answer:
Section: 19-13
33) Provide the structure of benzoic acid.
Answer:
Section: 19-13
3%) Provide the structure of anisole.
Answer:
Section: 19-13
3.) an one distin"uish a*on" the three iso*eric +ylenes usin"
13
)?H1 &+!lain.
Answer: Ies. (n the !roton decou!led
13
)?H s!ectra of these three iso*ers' different
nu*bers of !ea:s are !resent. 5he ortho iso*er has %' the meta iso*er has .' and the para
iso*er has 3.
Section: 19-13
31
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3/) Provide the best na*e for the or"anic co*!ound below.
Answer: o-!ro!yl!henol or 2-!ro!yl!henol
Section: 19-13
33) Provide the best na*e for the or"anic co*!ound below.
Answer: m-toluidine
Section: 19-13
39) )a*e the followin" structure.
A) 2-chlorobenzoic acid
,) 3-chlorobenzoic acid
) 2-chlorobenzaldehyde
-) 3-chlorobenzaldehyde
&) 3-chloroaceto!henone
Answer: ,
Section: 19-13
32
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39) @ive the best na*e for the structure.
A) 2-*ethyl-1'3'.-trinitrobenzene
,) 1'3'.-tria*inotoluene
) 1'3'.-trinitrotoluene
-) 2'%'/-tria*inotoluene
&) 2'%'/-trinitrotoluene
Answer: &
Section: 19-13
9$) @ive three different correct na*es for the structure.
Answer: 2-a*ino-%-*ethyl!henol
2-hydro+y-.-*ethylaniline
3-a*ino-%-hydro+ytoluene
Section: 19-13
91) -raw !-a*inobenzoic acid.
Answer:
Section: 19-13
33
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92) 0hich of the followin" co*!ounds reacts *ost slowly durin" nitration1
A) (
,) ((
) (((
-) (2
&) 2
Answer:
Section: 19-1%
93) 0hich of the followin" co*!ounds reacts *ost ra!idly durin" nitration1
A) (
,) ((
) (((
-) (2
&) 2
Answer: -
Section: 19-1%
3%
o!yri"ht # 2$1% Pearson &ducation' (nc.
9%) 0hich of the followin" substrates is an electron donatin" "rou! overall1
A) J,r
,)
) JA7
3
-)
&) Jl
3
Answer:
Section: 19-1%
9.) 0hich of the followin" substrates is an electron withdrawin" "rou! overall1
A) (
,) ((
) (((
-) (2
&) 2
Answer: &
Section: 19-1%
9/) 0hich of the followin" substituents acts as a *oderate activator and oK! director in
electro!hilic aro*atic substitution reactions1
A) -,r
,) -SA
3
7
) -A
2
7
-) -)7AH
&) -7A
Answer: -
Section: 19-1%
3.
o!yri"ht # 2$1% Pearson &ducation' (nc.
93) 0hich of the followin" aro*atic rin"s is al:ylated *ost ra!idly by 7
3
7
2
lKAll
3
1
A) benzene
,) ethylbenzene
) chlorobenzene
-) benzenesulfonic acid
&) nitrobenzene
Answer: ,
Section: 19-1%
99) Han: the followin" "rou!s in order of increasin" activatin" !ower in electro!hilic aro*atic
substitution reactions:
-A7
3
' -AA7
2
7
3
' -7
2
7
3
' -,r.
Answer: -,r F -7
2
7
3
F -AA7
2
7
3
F -A7
3
Section: 19-1%
99) 0hich of the followin" co*!ounds reacts *ost ra!idly with 7)A
3
K7
2
SA
%
1
A) toluene
,) anisole
) nitrobenzene
-) benzonitrile
&) fluorobenzene
Answer: ,
Section: 19-1%
9$) <ist the followin" co*!ounds in order of decreasin" reactivity toward electro!hilic aro*atic
substitution: toluene' benzene' fluorobenzene' nitrobenzene' !henol.
Answer: !henol E toluene E benzene E fluorobenzene E nitrobenzene
Section: 19-1%
91) (n electro!hilic aro*atic substitution reactions' a chlorine substituent is LLLLLLLL.
A) a deactivator and a m-director
,) a deactivator and an o'p-director
) an activator and a m-director
-) an activator and an o'p-director
&) none of the above
Answer: ,
Section: 19-1.
3/
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92) 0hich of the followin" structures is the *ost i*!ortant contributor to the resonance hybrid
for*ed when toluene under"oes !ara nitration1
A) (
,) ((
) (((
-) (2
&) 2
Answer: A
Section: 19-1.
33
o!yri"ht # 2$1% Pearson &ducation' (nc.
93) 0hich of the followin" structures is the *ost i*!ortant contributor to the resonance hybrid
for*ed when anisole under"oes o-bro*ination1
A) (
,) ((
) (((
-) (2
&) 2
Answer: -
Section: 19-1.
39
o!yri"ht # 2$1% Pearson &ducation' (nc.
9%) 0hat is the *a;or !roduct of the followin" reaction1
A) (
,) ((
) (((
-) (2
&) 2
Answer:
Section: 19-1.
9.) Provide the *a;or or"anic !roductBs) of the reaction below.
Answer:
Section: 19-1.
9/) Provide the *a;or or"anic !roductBs) of the reaction below.
Answer:
Section: 19-1.
39
o!yri"ht # 2$1% Pearson &ducation' (nc.
93) -raw the four *a;or resonance structures of the carbocation inter*ediate in the reaction of
anisole with 7)A
3
K7
2
SA
%
to yield p-nitroanisole.
Answer:
Section: 19-1.
99) -raw the three *a;or resonance structures of the carbocation inter*ediate in the reaction of
aceto!henone with 7)A
3
K7
2
SA
%
to yield o-nitroaceto!henone. ircle the resonance for*
which is less stable than the other two.
Answer:
Section: 19-1.
99) <ist the followin" co*!ounds in order of decreasin" basicity.
Answer:
Section: 19-1.
%$
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1$$) <ist the followin" co*!ounds in order of decreasin" acidity.
Answer:
Section: 19-1/
1$1) 0hich of the followin" *onoal:ylbenzenes under"o nitration in 7)A
3
K7
2
SA
%
to yield a
!roduct *i+ture with the hi"hest ratio1
A) toluene
,) ethylbenzene
) !ro!ylbenzene
-) iso!ro!ylbenzene
&) tert-butylbenzene
Answer: A
Section: 19-13
1$2) 0hat factors affect the orthoK!ara ratio in electro!hilic aro*atic substitution reactions1
Answer: ,ased solely on !robability' one would e+!ect *ore of the ortho !roduct because there
are two ortho !ositions available to the inco*in" electro!hile versus only on !ara !osition.
7owever' the ortho !osition is sterically hindered relative to the !ara !osition. onse6uently' the
!ara !roduct will be "enerated !referentially if either the substituent on the rin" or the attac:in"
electro!hile is lar"e.
Section: 19-13
%1
o!yri"ht # 2$1% Pearson &ducation' (nc.
1$3) 0hat isKare the !roductBs) fro* the followin" reaction1
A) (
,) ((
) (((
-) (2
&) no reaction
Answer: &
Section: 19-19
1$%) &+!lain why nitrobenzene can be used as a solvent for 4riedel-rafts al:ylation.
Answer: ,ecause of the deactivatin" nature of the )A
2
"rou!' it will not under"o a 4..
reaction.
Section: 19-19
1$.) &+!lain why direct nitration of aniline yields' a*on" other !roducts' m-nitroaniline.
Answer: (n acidic *edia' the basic a*ino "rou! for*s a !rotonated a**oniu* ion which is a
*eta director.
Section: 19-19
1$/) Provide the structure of the *a;or or"anic !roduct of the followin" reaction.
Answer: )o reaction. 5he rin" is too deactivated by the acyl substituent to under"o 4riedel-
rafts al:ylation.
Section: 19-19
%2
o!yri"ht # 2$1% Pearson &ducation' (nc.
1$3) 0hat is the *a;or or"anic !roduct that results fro* the followin" se6uence1
A) styrene
,) !ro!ylbenzene
) iso!ro!ylbenzene
-) p-ethylaniline
&) 2-!henyl-1-!ro!ana*ine
Answer: &
Section: 1.-19
1$9) 0hat is the *a;or or"anic !roduct of the reaction shown below1
Answer:
Section: 1.-19
1$9) 0hat is the best *ethod for carryin" out the followin" reaction1
A) (
,) ((
) (((
-) (2
&) 2
Answer: ,
Section: 19-19
%3
o!yri"ht # 2$1% Pearson &ducation' (nc.
11$) 0hich is the best *ethod for carryin" out the followin" reaction1
A)
8
AA7M 7)A
3
K7
2
SA
%
,) 7
3
lKAll
3
M 7)A
3
K7
2
SA
%
M N?nA
%
K7
8
' heat
) 7
3
lKAll
3
M N?nA
%
K7
8
' heatM 7)A
3
K7
2
SA
%
-) 7)A
3
K7
2
SA
%
M 7
3
lKAll
3
M N?nA
%
K7
8
' heat
&) 7)A
3
K7
2
SA
%
M
8
AA7
Answer:
Section: 19-19
111) 0hich is the best *ethod for carryin" out the followin" reaction1
A) (
,) ((
) (((
-) (2
&) 2
Answer: &
Section: 19-19
112) 0hich of the followin" is the best *ethod for !re!arin" m-chloroaniline fro* benzene1
A) )7
3
M l
2
KAll
3
,) l
2
KAll
3
M )7
3
) l
2
KAll
3
M 7)A
3
K7
2
SA
%
M SnK7l' 7A
-
-) 7)A
3
K7
2
SA
%
M l
2
KAll
3
M SnK7l' 7A-
&) 7)A
3
K7
2
SA
%
M SnK7lM 7A
-
M l
2
KAll
3
Answer: -
Section: 19-19
%%
o!yri"ht # 2$1% Pearson &ducation' (nc.
113) Provide the *a;or or"anic !roducts of the reaction shown below.
Answer:
Section: 19-19
11%) 0hat se6uence of rea"ents can be used to acco*!lish the conversion shown below1
Answer: 1. ?"' &t
2
A
2. A+irane
3. 7
3
A
8
%. P
Section: 19-19
%.
o!yri"ht # 2$1% Pearson &ducation' (nc.
11.) (dentify the !roductBs) for the followin" reaction.
A)
,)
)
-)
&)
Answer: A'
Section: 19-19
%/
o!yri"ht # 2$1% Pearson &ducation' (nc.
11/) (dentify the !roductBs) for the followin" reaction.
A)
,)
)
-)
&)
4)
Answer: -' 4
Section: 19-19
%3
o!yri"ht # 2$1% Pearson &ducation' (nc.
113) @ive the !roductBs) for each ste! of the followin" reaction.
Answer:
Section: 19-19
%9
o!yri"ht # 2$1% Pearson &ducation' (nc.
119) @ive the best !roductBs) for the reaction.
A)
,)
)
-)
&) no reaction
Answer: &
Section: 19-19
%9
o!yri"ht # 2$1% Pearson &ducation' (nc.
119) 0hat se6uence of rea"ents can be used to *a:e m-bro*obutylbenzene fro* benzene1
Answer:
Section: 19-19
12$) 0hat se6uence of rea"ents can be used to *a:e m-butylbenzoic acid fro* benzene1
Answer:
Section: 19-19
121) 0hat se6uence of rea"ents can be used to *a:e p-butylbenzenesulfonic acid fro* benzene1
Answer:
Section: 19-19
.$
o!yri"ht # 2$1% Pearson &ducation' (nc.
122) 0hat is the *a;or !roduct of the followin" reaction1
A) (
,) ((
) (((
-) (2
&) 2
Answer: &
Section: 19-2$
123) Provide a series of synthetic ste!s by which 2-bro*o-%-nitrobenzoic acid can be !re!ared
fro* toluene.
Answer:
1) 7)A
3
' 7
2
SA
%
2) ,r
2
' 4e,r
3
3) N?nA
%
' 7
8
Section: 19-2$
.1
o!yri"ht # 2$1% Pearson &ducation' (nc.
12%) 0hat is the *a;or !roduct of the followin" reaction1
A) (
,) ((
) (((
-) (2
&) 2
Answer: ,
Section: 19-2$
12.) Provide the structure of the *a;or *ononitration !roduct of the co*!ound below.
Answer:

Section: 19-2$
12/) Provide the structure of the *a;or *ononitration !roductBs) of the co*!ound below.
Answer:
Section: 19-2$
.2
o!yri"ht # 2$1% Pearson &ducation' (nc.
123) Provide the structure of the *a;or or"anic !roduct of the followin" reaction.
Answer:
Section: 19-2$
129) @ive the !roductBs) for the followin" reaction.
Answer:
Section: 19-2$
.3
o!yri"ht # 2$1% Pearson &ducation' (nc.
129) @ive the !roductBs) for the followin" reaction.
Answer:
Section: 19-2$
13$) 0hat is the best *ethod for the !re!aration of p-chlorotoluene in hi"h yield1
A) start with benzeneM *ethylateM chlorinate
,) start with benzeneM chlorinateM *ethylate
) start with tolueneM chlorinate
-) start with chlorobenzeneM *ethylate
&) start with p-a*inotolueneM )a)A
2
K7l' $DM ul
Answer: &
Section: 19-21
131) 0hat is the best *ethod for the !re!aration of m-dibro*obenzene fro* benzene1
A) nitrateM SnK7lM )a)A
2
K7l' $DM bro*inate twice
,) nitrateM SnK7lM )a)A
2
K7l' $DM bro*inate twiceM 7
3
PA
2
) nitrateM SnK7lM )a)A
2
K7l' $DM 7
3
PA
2
M bro*inate twice
-) nitrateM bro*inateM SnK7lM )a)A
2
K7l' $DM u,r
&) bro*inate twice
Answer: -
Section: 19-21
.%
o!yri"ht # 2$1% Pearson &ducation' (nc.
132) 0hich rea"ent is least li:ely to be used in the conversion shown1
A) )a
2
r
2
A
3
,) 7)A
3
) Sn
-) )a)A
2
&) 7l
Answer: A
Section: 19-21
133) Provide the structure of the *a;or or"anic !roduct of the followin" reaction.
Answer:
Section: 19-21
13%) 0hat se6uence of rea"ents can be used to acco*!lish the conversion shown below1
Answer:
1. 7)A
3
' 7
2
SA
%
2. ,r
2
' 4e,r
3
3. SnK7l
%. 7A
-
.. )a)A
2
' 7,r' $ D
/. 7,4
%
Section: 19-21
..
o!yri"ht # 2$1% Pearson &ducation' (nc.
13.) (dentify the best !roduct for the reaction.
A)
,)
)
-)
&)
Answer: A
Section: 19-21
./
o!yri"ht # 2$1% Pearson &ducation' (nc.
13/) (dentify the best !roduct for the reaction.
A)
,)
)
-)
&)
Answer: A
Section: 19-21
.3
o!yri"ht # 2$1% Pearson &ducation' (nc.
133) (dentify the best !roduct for the reaction.
A)
,)
)
-)
&)
Answer:
Section: 19-21
.9
o!yri"ht # 2$1% Pearson &ducation' (nc.
139) 0hat is one of the !roducts of the followin" reaction1
A) (
,) ((
) (((
-) (2
&) 2
Answer:
Section: 19-22
139) 0hat rea"ent is used to convert an arenediazoniu* salt into a fluoroarene1
A) 7,4
%
,) 4
2
) 74
-) ,4
3
&) ,
2
4
/
Answer: A
Section: 19-22
.9
o!yri"ht # 2$1% Pearson &ducation' (nc.
1%$) (dentify the best !roduct for the reaction.
A)
,)
)
-)
&)
Answer:
Section: 19-23
/$
o!yri"ht # 2$1% Pearson &ducation' (nc.
1%1) (dentify the *a;or !roduct for the reaction.
A)
,)
)
-)
&)
Answer:
Section: 19-23
/1
o!yri"ht # 2$1% Pearson &ducation' (nc.
1%2) 0hich of the followin" is *ost reactive toward nucleo!hilic aro*atic substitution1
A) (
,) ((
) (((
-) (2
&) 2
Answer: -
Section: 19-2%
1%3) Provide a detailed' ste!wise *echanis* for the followin" reaction.
Answer:
Section: 19-2%
/2
o!yri"ht # 2$1% Pearson &ducation' (nc.
1%%) -raw the four *a;or resonance structures of the inter*ediate which results when o-
nitrochlorobenzene is treated with )aA7.
Answer:
Section: 19-2%
1%.) Provide a series of synthetic ste!s by which p-bro*oanisole can be !re!ared fro* benzene.
Answer: 1) l
2
' 4el
3
2) 7)A
3
' 7
2
SA
%
3) )aA7
3
%) Sn' 7l
.) )a)A
2
' 7l' $D
/) u,r
Section: 19-2%
/3
o!yri"ht # 2$1% Pearson &ducation' (nc.
1%/) (dentify the *a;or !roductBs) for the reaction.
A)
,)
)
-)
&)
Answer:
Section: 19-2%
/%
o!yri"ht # 2$1% Pearson &ducation' (nc.
1%3) (dentify the *a;or !roductBs) for the reaction.
A)
,)
)
-)
&)
Answer: ,'
Section: 19-2%
/.
o!yri"ht # 2$1% Pearson &ducation' (nc.
1%9) 0hich of the followin" under"oes solvolysis in water *ore ra!idly1
Answer:
Section: 19-99
1%9) 0hat is the *a;or !roduct fro* the followin" reaction1
A) (
,) ((
) (((
-) ( and (( e6ually
&) ( and ((( e6ually
Answer: A
Section: 99
//
o!yri"ht # 2$1% Pearson &ducation' (nc.
1.$) 0hat is the *a;or !roduct of the followin" reaction1
A) (
,) ((
) (((
-) A and , e6ually
&) A and e6ually
Answer:
Section: 99
1.1) 0hat is the na*e of the followin" co*!ound1
Answer: 1'3-dinitrona!hthalene
Section: 99
1.2) Provide the structure of the *a;or or"anic !roduct of the followin" reaction.
Answer:
Section: 99
/3
o!yri"ht # 2$1% Pearson &ducation' (nc.
1.3) 0hich of the followin" is the *ost acidic1
A) (
,) ((
) (((
-) (2
&) 2
Answer: &
Section: A1.-.
1.%) Provide the *a;or resonance structures of the ion which results when the *ost acidic
hydro"en of cyclo!entadiene is lost.
Answer:
Section: A1.-.
1..) -oes cyclohe!tatriene have a hi"her or lower !Na than cyclo!entadiene1 &+!lain.
Answer: yclohe!tatriene is a wea:er acid than cyclo!entadiene and thus has a hi"her !Na.
yclo!entadiene is *ore acidic because the cyclo!entadienyl anion which results u!on
de!rotonation is aro*atic and thus *ore stable than the corres!ondin" con;u"ate base of
cyclohe!tatriene.
Section: A1.-.
/9
o!yri"ht # 2$1% Pearson &ducation' (nc.
1./) ?ar: the *ost basic site in the *olecule below with an asteris:.
Answer:
Section: A1.-.
/9
o!yri"ht # 2$1% Pearson &ducation' (nc.