Prep 101 Booklet (2013) Part 8
Chem212 Exam Booklet
@PreP101
would react the fastest in an Of the compounds below which
9.
electrophilic
substitution?
@[-e.@l€< @"@,,>ei-o
I I
I
I
10.
(Hückel) stability? Of the compounds below which has aromatic
IlY.Jt
/n êl
x
I
ryv/
I
11.
Provide suitable reagents for the following transformâtion
o
o
ll
,=-'
"C\?
12.
o\)
aromatic species: lndicate how the structures shown below could be converted to an
x
ô
Solutions will be posted at www.prep10l.com/solutlons
153
Chem212 Exam Booklet with AlClg and chloroethane' circle the ones won't react compounds' Of the following
ô' ctr'' Ctr:: «
il
etr'-o^ o
CI
NH!
C
sorH
Br
14.Whichofthereactionbelowwillnotproceedtogivetheproductindicated?
o+ry; o
O*- o,
l!...,,,_...
ç+x=O^
o+ry'o" o+-ry''
Solutions will be posted at www,prep10l.com/solutions
154
OPrep101 15.
Chem212 Exam Booklet
Provide an efflcient synthesis for the following transformâtion:
cl ? .-----r.--------
ô_
cc13
Provide an efficient synthesis for the following transformation:
(^) \r,
U
-.- -:---.'-
Solutions will be posted at www.preplOl'com/solutions
155
-
L*k /", Chem212 Exam Booklet synthesis for the following transformation (need more than 4 steps).
O,N
6,ÿ
?
---.-->
I
18.
Each of the following disub benzenes will be halogenated.
which of the following does the
arrow NOT point to the maior site of halogenation?
oot
^,h ctoll
ffiol
,*4
BztrrrP
I
Solutions will be posted at www.prepl'ol'.com/solutlons
156
Chem2L2 Exam Booklet
@Prep101
19.
Which dibromobenzene can yield only one mononitro derivative?
ÀJ q'fibr+mo-ïeazer:e
Ei
C)
20.
in -
E-
f,i brsrnobr:rrr
Di {o:e thar- or-e oi :hese E) )'anG c! cherr:
Ér!Ê
=1b=crnr:beazene
Reaction of benzene with (CH3»CCHrCI with AlCl3 principally results in:
c+c(cth
ut)
sü(cr-hh$+r
CllzCHtcH(CHl)2
Àir \t ,i_/l
ÀÀ-
lI
lt
CFbCFICF?CFhCt+J
(ftlrLçcH:cH]
Solutions will be posted at www.prepl01.com/solutions
157
OPrep101
Chem212 Exam Booklet
Appendix: lsoprene and Terpenes Terpenes are naturally occurring molecules, present in plants, ând consisl of a carbon chain with alternating single and double bonds.
A terpene is formed from a combination of at least 2 isoprenes and constitutes the basic structure of sterols (4Jused ring structure).
The following figure shows combination of isoprenes to form terpenes, squalene and the familiar fused ring structure of sterols. OPP indicates oxygen attached to a pyrophosphate, which indicates the molecule is "activated" to undergo reactions.
Mechanism for Terpene Formation:
\// \// ///
L--o-1-I r_
fl r
o-T-o-1-o
oo
o-1_
oo
\./
"
Yÿ
l
J(J(J
Monolerpene
.\.
^
t '-:' 'G-p-o-p-o.lôô l_ i_ I
Y
I ..".,_. -
sqratene
I ,a\/*
-î-,y* f-Y ;
J.,
Lan0sl€rol
Solutions will be posted at www.prepl0l.com/solutions
158
Chem212 Exam Booklet
Practice Problem:
Circle the lsoprene units in each of the following terpenes:
I
Zingiberene
(lrom oil ol ginger)
/.|-Selinene
(lrom oil ol celery)
(tromiii ol cloves)
sôlutiôns will be posted at www.preplOl.com/solutions
159
OPreplol
Chem212 Exam Booklet
EXAM WR]TING TIPS
ituftiple Choice Tips Choice TiDs As you browse through, make a
different kind of notation next to those questions which seem easy, those which seem difficult but you can probably solve, and those which completely baffle you. Allocate your time according to the relative worth of questions. Try to save a few minutes at the end for review and revision. Remember: your first answer may not always be your best answer.
can Answer Don't waste time laboring over troublesome questions at the start. Be sure to get credit for items you know well. Then, do questions that are difficult but you think you can solve. Last, take a stab at questions that baffle you but you can maybe guess the answer by elimination.
sytÀrtid, Another approach is to answer all the questions from the same section of the course in a row. This will help offset the mixing of questions inherent in the design of the test. please note that this approach demands that care be taken that answer sheets âre correctly completed and that all questions have been answered. The other benefit of this approach is that it allows you to spot clues in one question that may help solve another from the same section of the course lB"
Now try the questions you could not do on the first attempt. Sometimes the answer will occur to you simply because you are more relaxed after having answered other questions. sometimes, too, your ans\^/er to one question provides a clue to the answer of another.
the stem of each question, while covering the answers, and try to ânticipate the right answer by using recall. lf the answer you anticipated is one of the options, it is probably right. Read
Read them at least twice. Circle or underline key words il questions. Avoid jumping to conclusions about what you think the question asks. some of the most common mistakes on multiple-choice exams stem from carelessly misreading the question. some wrong answers are specifically designed to penalize students who have not understood the question correctly.
Multiple choice tests examine your ability to read carefully and thoughtfully as much as they test your ability to recall and reason. Read the questions very carefully. Take into account qualifying words such as NOT, MAy, SOMETIMES, CAN, MUST....
)on't Guess Prematur€ Read ALL the answers and try to identify the "best" answer. lf you are uncertain and time is not a factor, leave the question and come back to it later. Make a notation next
to the question so you know to return to it later. Make one form of notation next to difficult
Solutions will be posted at www.prep101.com/solutions
160
l I
Chem212 Exam Booklet
OPrep101
questions you think you may be able to solve; make another form of notation next to difficult questions that completely baffle you. Return to the former first; leave the latter to the end. Thât way, if you run out of time, you only miss questions you would probably get wrong anyway select the most completely correct answer. More than one answer may be
technically correct.
Eliminate unlikely answers. Many questions only have 2 likely answers and "throwaways". Try to spot these and eliminate them'
t"{h" f".t
2
Utilize information that you have gained in working through other questions Be that the information relevant to one question is sometimes given away by another
"l"rt item on the exam.
ffiffi, Ërr"
f
,.all of the above" as ân option, if you know 2 options are For example, on items with eliminate it and "all of the f of the above" !!u§! be right. lf you are §!I9 1 option is wrong'
above".
:
Answers that are broâd, sweeping generalizations
ffiersthatarequalifiedstatements(often,sometime5, may, etc.) tend to be right.
ffiTffi:BeskepticaloflonganswerspackedWithlotsofiargon.Theyoftenlook may not describe the correct logical right because they have the rigit words in them, but they relationships between these words
@:lfyouhave.time,reviewYouranswersandchangetheonesyou if you have a good reason for doing so' For instan-ce'
but only believe are wrong. change "nrui"rs, your response to the previous four changing an answer from, say, selection "b" simply because have the same item qr"rlioi, *", .lro "b" and you cannot believe that five questions in a row would be flexible in your approach' as the correct response, is likely not a good reason;
Solutions will be posted at www.prepl01'com/solutions
161
+1."
Tn
--, //.. / . s/ooKt,t! e7 .'I ,\J
"cder
Az
"ê
oî a ^eori,u;h c,/
/
a /o,ng
inqoflo_c_
AroM
nLlr, /
"-> 4o< '"
à*,f li"Qay:::
:Z,gl, *a
jRg.'R ,rq"--- t,&e sf/4 t têêKü
-
"/ /4. *...^- *l^, -, Z 7*,"2 {1 u-"efi;vc t
,,
-ÆLu",-,,. I ft^,,. e;=. J ttYate I |
.''-OO
O//Less elocfra*of* -.rMr. (/ \/
yloRe srtBt/_
."
Less s71s.,
--->vbc reet,a^.,///ou
til
Yd'c st*aç
\' ry*-"-,*. I,Irlorl,*
çT1azé.
L€ss
rdy'J_æ, , /r, Vs.
_JÇ,
,lA,/,
,Llr7ti
J*f *:
o
-
^,,.o..
,$
p {
7r/ "//,-"
d,4 thoe Sé,4
---oo
I
,tÇ
I
srrarn c(*oo |IORE SîAELÇ
O'
Or[,1"1
- tlL,e S-J*r(u.
(czt s)
Â"rÉ
/tnea..s
*n sà(L - 71* *.*,li* fu* ,r,
--?-/ô,p
( sot
s\
- ff1ffi',i;ffTgtt t*
ns ll, YJ Y; cr, Br-,
>t(,,74t. *rtq/"l"
in %._ar(fi.u,.-
( to 4U ' rye;":#î 2,1ft, , ,d*/;a n Wr;Lü .*lh ic_a ,,@Çn / !,î;;oüA t,W il*d/o "iru*,/,^ .v,,/o 4i '-"ù' 'ÿ-.r. , ,r!"Wl '?r't" c'L*4s 'b4,,7'L"'/ r* */ * - *; -"*, -ûhr R-d'--rcr /r. J' /f-"'-",w./,^ ,1x'. rWlia"
'71, (ru
.
/irfu fuâ CHt-Cilr-\, + No7H ffi
cr1)ct-lzgr
I
N^SH
h
gz7:ii,*W n.*"2, ,/,^ ya, i&"-zr" ,/ ,tn / W 'T; Tt.'",/l^ ,,,**bt/"', 11,ald U___ ,t .û_';;î _LA,:i ,' /r.!"- r,,*, /"*,71j*)*i,*ymü aouu" le rS",Nk ;,-M,:,,' i^r_ * LG?,k, skra"y4\ weat4^ wealo^ oA" oAO ,Lry^,
suo ,*P^) ry ?r"r*" :rL b2"
Y:P*,h,l rt
{. J-*. o"X
/Yf?4n
Àr,tu. Lrot a-
tnfln^-
\,* t
,i;t'*r/^4,,o/L^ .
.tç J.üou
f
^ bl*tr,t.//,,t
,.f
C\l'...4--/
/a?ô'
"t5
r
-
.'\-
â
YH-
§^ÿ,_v^.,, BI\
in't^(l
I
'l ,e"L, /pt,
2u:- fosh **l;ool
c.,-c61,-6"lrl^il,Ë*
:,;uAtc
a t*-)il;
4k ,/*ÿ;,,a )o no*,t"/ n':in '
,i#:
I
",.
tl
'r
4prt"rt_R"A*l
Rearl;c,a
o \,., A=---=F \)
L. *- A O'
1>
Resofiance
sl^liLrr)
ôp 6 ="6Lhr *^*n*Wh,:*,ffh o @
l-rl
d $"6.. é,-* ô , , -'o î;t/iù|vÀ', fr r,,rnl
@
Et I
ç,
;ik-"
%
tl
a s"Lo,in
/t t , _ tussr,/4/ :
w-;o*,, P'l*
. 4,, "ur4 ÿ*c7" ^/'4 --,/h n/ ' oJ.*, '* t
/Ou
t
7'-'.
*-ç.^;-r ff:Yffi *,Pil,#w*':*
y* :'-Z ttW; @
NBs
,
^/BÇ
-"%i,X6,
,,,H ^ o(\n w o .\7 W, (R esotto*rr\t
ru'/, I
*lL çdt-r*/.tu /'") t"
^ \ "rd|olr*""5.i''
\*'"i
/' \ t /"''
O ls
a ? iolv,li'nq
'
lo'
3Y{,nr
r
\
t*--, hhrÀ hrl *".-, qry"*w', I Vf"l é q,iætlr ->5 U a.h',^br, d0
,fu^ltys r'z=-
wù',s
-----v ô
L
'f'fu b**
lPor"
=? I
Vs.
,{,
uL *-
?/ç
4tr1'fut%4* î\/ =l/*- V..z *n o 'Vr,'k /^'ry'I Alct-3
"
S,nfi'*' o,*11.
o
)^",!!,ll'1,r" t, ,l.
raa
I
Ar*l-u"!
D*hlY
Bq
(X,-^\^ _/.\
--/n'1,7r.21"-
"- y,SN,ls tt, = [o/k4 ** ; k k -->€/z
,V ^/1,"*(
I l" l"H qt zrya) J*/) 4*{ l^ *,^,Ç o,r.,,*7r4 o/,,r,"a;/. fu -> Alwry",^* otJç*" carb,.,{»^ i"--U-".* (e3. n assiyru-.,,.&
-->ut^1,1,
ryh
d,üi1a- oF ux)
->P"tl;n J,*.6" e,. alKe,^n'/tJU é^i, ^*"r*":# :=
æ 19ô-
@PreP101
would react the fastest in an Of the compounds below which
9.
electrophilic
substitution?
@[-e.@l€< @"@,,>ei-o
I I
I
I
10.
(Hückel) stability? Of the compounds below which has aromatic
IlY.Jt
/n êl
x
I
ryv/
I
11.
Provide suitable reagents for the following transformâtion
o
o
ll
,=-'
"C\?
12.
o\)
aromatic species: lndicate how the structures shown below could be converted to an
x
ô
Solutions will be posted at www.prep10l.com/solutlons
153
Chem212 Exam Booklet with AlClg and chloroethane' circle the ones won't react compounds' Of the following
ô' ctr'' Ctr:: «
il
etr'-o^ o
CI
NH!
C
sorH
Br
14.Whichofthereactionbelowwillnotproceedtogivetheproductindicated?
o+ry; o
O*- o,
l!...,,,_...
ç+x=O^
o+ry'o" o+-ry''
Solutions will be posted at www,prep10l.com/solutions
154
OPrep101 15.
Chem212 Exam Booklet
Provide an efflcient synthesis for the following transformâtion:
cl ? .-----r.--------
ô_
cc13
Provide an efficient synthesis for the following transformation:
(^) \r,
U
-.- -:---.'-
Solutions will be posted at www.preplOl'com/solutions
155
-
L*k /", Chem212 Exam Booklet synthesis for the following transformation (need more than 4 steps).
O,N
6,ÿ
?
---.-->
I
18.
Each of the following disub benzenes will be halogenated.
which of the following does the
arrow NOT point to the maior site of halogenation?
oot
^,h ctoll
ffiol
,*4
BztrrrP
I
Solutions will be posted at www.prepl'ol'.com/solutlons
156
Chem2L2 Exam Booklet
@Prep101
19.
Which dibromobenzene can yield only one mononitro derivative?
ÀJ q'fibr+mo-ïeazer:e
Ei
C)
20.
in -
E-
f,i brsrnobr:rrr
Di {o:e thar- or-e oi :hese E) )'anG c! cherr:
Ér!Ê
=1b=crnr:beazene
Reaction of benzene with (CH3»CCHrCI with AlCl3 principally results in:
c+c(cth
ut)
sü(cr-hh$+r
CllzCHtcH(CHl)2
Àir \t ,i_/l
ÀÀ-
lI
lt
CFbCFICF?CFhCt+J
(ftlrLçcH:cH]
Solutions will be posted at www.prepl01.com/solutions
157
OPrep101
Chem212 Exam Booklet
Appendix: lsoprene and Terpenes Terpenes are naturally occurring molecules, present in plants, ând consisl of a carbon chain with alternating single and double bonds.
A terpene is formed from a combination of at least 2 isoprenes and constitutes the basic structure of sterols (4Jused ring structure).
The following figure shows combination of isoprenes to form terpenes, squalene and the familiar fused ring structure of sterols. OPP indicates oxygen attached to a pyrophosphate, which indicates the molecule is "activated" to undergo reactions.
Mechanism for Terpene Formation:
\// \// ///
L--o-1-I r_
fl r
o-T-o-1-o
oo
o-1_
oo
\./
"
Yÿ
l
J(J(J
Monolerpene
.\.
^
t '-:' 'G-p-o-p-o.lôô l_ i_ I
Y
I ..".,_. -
sqratene
I ,a\/*
-î-,y* f-Y ;
J.,
Lan0sl€rol
Solutions will be posted at www.prepl0l.com/solutions
158
Chem212 Exam Booklet
Practice Problem:
Circle the lsoprene units in each of the following terpenes:
I
Zingiberene
(lrom oil ol ginger)
/.|-Selinene
(lrom oil ol celery)
(tromiii ol cloves)
sôlutiôns will be posted at www.preplOl.com/solutions
159
OPreplol
Chem212 Exam Booklet
EXAM WR]TING TIPS
ituftiple Choice Tips Choice TiDs As you browse through, make a
different kind of notation next to those questions which seem easy, those which seem difficult but you can probably solve, and those which completely baffle you. Allocate your time according to the relative worth of questions. Try to save a few minutes at the end for review and revision. Remember: your first answer may not always be your best answer.
can Answer Don't waste time laboring over troublesome questions at the start. Be sure to get credit for items you know well. Then, do questions that are difficult but you think you can solve. Last, take a stab at questions that baffle you but you can maybe guess the answer by elimination.
sytÀrtid, Another approach is to answer all the questions from the same section of the course in a row. This will help offset the mixing of questions inherent in the design of the test. please note that this approach demands that care be taken that answer sheets âre correctly completed and that all questions have been answered. The other benefit of this approach is that it allows you to spot clues in one question that may help solve another from the same section of the course lB"
Now try the questions you could not do on the first attempt. Sometimes the answer will occur to you simply because you are more relaxed after having answered other questions. sometimes, too, your ans\^/er to one question provides a clue to the answer of another.
the stem of each question, while covering the answers, and try to ânticipate the right answer by using recall. lf the answer you anticipated is one of the options, it is probably right. Read
Read them at least twice. Circle or underline key words il questions. Avoid jumping to conclusions about what you think the question asks. some of the most common mistakes on multiple-choice exams stem from carelessly misreading the question. some wrong answers are specifically designed to penalize students who have not understood the question correctly.
Multiple choice tests examine your ability to read carefully and thoughtfully as much as they test your ability to recall and reason. Read the questions very carefully. Take into account qualifying words such as NOT, MAy, SOMETIMES, CAN, MUST....
)on't Guess Prematur€ Read ALL the answers and try to identify the "best" answer. lf you are uncertain and time is not a factor, leave the question and come back to it later. Make a notation next
to the question so you know to return to it later. Make one form of notation next to difficult
Solutions will be posted at www.prep101.com/solutions
160
l I
Chem212 Exam Booklet
OPrep101
questions you think you may be able to solve; make another form of notation next to difficult questions that completely baffle you. Return to the former first; leave the latter to the end. Thât way, if you run out of time, you only miss questions you would probably get wrong anyway select the most completely correct answer. More than one answer may be
technically correct.
Eliminate unlikely answers. Many questions only have 2 likely answers and "throwaways". Try to spot these and eliminate them'
t"{h" f".t
2
Utilize information that you have gained in working through other questions Be that the information relevant to one question is sometimes given away by another
"l"rt item on the exam.
ffiffi, Ërr"
f
,.all of the above" as ân option, if you know 2 options are For example, on items with eliminate it and "all of the f of the above" !!u§! be right. lf you are §!I9 1 option is wrong'
above".
:
Answers that are broâd, sweeping generalizations
ffiersthatarequalifiedstatements(often,sometime5, may, etc.) tend to be right.
ffiTffi:BeskepticaloflonganswerspackedWithlotsofiargon.Theyoftenlook may not describe the correct logical right because they have the rigit words in them, but they relationships between these words
@:lfyouhave.time,reviewYouranswersandchangetheonesyou if you have a good reason for doing so' For instan-ce'
but only believe are wrong. change "nrui"rs, your response to the previous four changing an answer from, say, selection "b" simply because have the same item qr"rlioi, *", .lro "b" and you cannot believe that five questions in a row would be flexible in your approach' as the correct response, is likely not a good reason;
Solutions will be posted at www.prepl01'com/solutions
161
+1."
Tn
--, //.. / . s/ooKt,t! e7 .'I ,\J
"cder
Az
"ê
oî a ^eori,u;h c,/
/
a /o,ng
inqoflo_c_
AroM
nLlr, /
"-> 4o< '"
à*,f li"Qay:::
:Z,gl, *a
jRg.'R ,rq"--- t,&e sf/4 t têêKü
-
"/ /4. *...^- *l^, -, Z 7*,"2 {1 u-"efi;vc t
,,
-ÆLu",-,,. I ft^,,. e;=. J ttYate I |
.''-OO
O//Less elocfra*of* -.rMr. (/ \/
yloRe srtBt/_
."
Less s71s.,
--->vbc reet,a^.,///ou
til
Yd'c st*aç
\' ry*-"-,*. I,Irlorl,*
çT1azé.
L€ss
rdy'J_æ, , /r, Vs.
_JÇ,
,lA,/,
,Llr7ti
J*f *:
o
-
^,,.o..
,$
p {
7r/ "//,-"
d,4 thoe Sé,4
---oo
I
,tÇ
I
srrarn c(*oo |IORE SîAELÇ
O'
Or[,1"1
- tlL,e S-J*r(u.
(czt s)
Â"rÉ
/tnea..s
*n sà(L - 71* *.*,li* fu* ,r,
--?-/ô,p
( sot
s\
- ff1ffi',i;ffTgtt t*
ns ll, YJ Y; cr, Br-,
>t(,,74t. *rtq/"l"
in %._ar(fi.u,.-
( to 4U ' rye;":#î 2,1ft, , ,d*/;a n Wr;Lü .*lh ic_a ,,@Çn / !,î;;oüA t,W il*d/o "iru*,/,^ .v,,/o 4i '-"ù' 'ÿ-.r. , ,r!"Wl '?r't" c'L*4s 'b4,,7'L"'/ r* */ * - *; -"*, -ûhr R-d'--rcr /r. J' /f-"'-",w./,^ ,1x'. rWlia"
'71, (ru
.
/irfu fuâ CHt-Cilr-\, + No7H ffi
cr1)ct-lzgr
I
N^SH
h
gz7:ii,*W n.*"2, ,/,^ ya, i&"-zr" ,/ ,tn / W 'T; Tt.'",/l^ ,,,**bt/"', 11,ald U___ ,t .û_';;î _LA,:i ,' /r.!"- r,,*, /"*,71j*)*i,*ymü aouu" le rS",Nk ;,-M,:,,' i^r_ * LG?,k, skra"y4\ weat4^ wealo^ oA" oAO ,Lry^,
suo ,*P^) ry ?r"r*" :rL b2"
Y:P*,h,l rt
{. J-*. o"X
/Yf?4n
Àr,tu. Lrot a-
tnfln^-
\,* t
,i;t'*r/^4,,o/L^ .
.tç J.üou
f
^ bl*tr,t.//,,t
,.f
C\l'...4--/
/a?ô'
"t5
r
-
.'\-
â
YH-
§^ÿ,_v^.,, BI\
in't^(l
I
'l ,e"L, /pt,
2u:- fosh **l;ool
c.,-c61,-6"lrl^il,Ë*
:,;uAtc
a t*-)il;
4k ,/*ÿ;,,a )o no*,t"/ n':in '
,i#:
I
",.
tl
'r
4prt"rt_R"A*l
Rearl;c,a
o \,., A=---=F \)
L. *- A O'
1>
Resofiance
sl^liLrr)
ôp 6 ="6Lhr *^*n*Wh,:*,ffh o @
l-rl
d $"6.. é,-* ô , , -'o î;t/iù|vÀ', fr r,,rnl
@
Et I
ç,
;ik-"
%
tl
a s"Lo,in
/t t , _ tussr,/4/ :
w-;o*,, P'l*
. 4,, "ur4 ÿ*c7" ^/'4 --,/h n/ ' oJ.*, '* t
/Ou
t
7'-'.
*-ç.^;-r ff:Yffi *,Pil,#w*':*
y* :'-Z ttW; @
NBs
,
^/BÇ
-"%i,X6,
,,,H ^ o(\n w o .\7 W, (R esotto*rr\t
ru'/, I
*lL çdt-r*/.tu /'") t"
^ \ "rd|olr*""5.i''
\*'"i
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