Chapter Sixteen MULTIPLE MULTIPLE CHOICE QUESTIONS
Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 1. What is the the correct I! I!"# "# name name for the follo$in% follo$in% compoun&' compoun&'
O
"( ,( #( D( E( "ns:
2)*ethyl)+) )+)heptanone -)*ethyl)) ))octanon none 6)I 6)Isopr opropy opyl)) l))oc octtanon anonee Iso/u o/utyl pr propyl pyl 0e 0etone 11) 11)Di Dim methy ethyl) l)) )he hept ptan anon onee ,
Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 2. What is the the correct structu structure re for -)methyl -)methyl))octa ))octanone' none' O
O
II
I
O O
O
I
"( ,( #( D( E( "ns:
I II III I D
162
III
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Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 3. What is the the correct I! I!"# "# name name for the follo$in% follo$in% compoun&' compoun&'
O
"( ,( #( D( E( "ns:
++) ++)Di Dim methy ethyl) l)2) 2)he hept ptan anon onee +)Et +)Ethy hyl)+ l)++ +)& )&im imet ethy hyl)* l)*et ethy hyl)2 l)2)o )oct ctan anone one +)Et +)Ethy hyl) l)+) +)me meth thyl yl)) 2)he 2)he4a 4ano none ne ++) ++)Di Dim methy ethyl) l)2) 2)oc octtanon anonee 33) 33)Di Dim methy ethyl) l)6) 6)he hept ptan anon onee "
Topic: Nomenclature Section: 16.2 Difficulty Level: Easy . What is the correct correct structure structure for ++)&imet ++)&imethyl)2) hyl)2)heptan heptanone' one' O
O
I
O
II
O
III
H
O
I
"( ,( #( D( E( "ns:
I II III I ,
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Topic: Nomenclature Section: 16.2 Difficulty Level: Easy +. " correct correct name for for the follo$in% follo$in% compoun& compoun& $oul& /e $hich $hich of those /elo$' /elo$' O H
"( ,( #( D( E( "ns:
2+) 2+)Di Dim methy ethyl) l)6) 6)he he4a 4ana nall 2+)D +)Dimethyl hylhe4a e4anal nal 2)"l&ehy&o hy&oiisohe ohe4ane 3+)D +)Dimethyl hylhept eptanone 1)5y 1)5y&r &ro) o)2 2+) +)&i &ime meth thyl yl)1 )1)h )he4 e4an anon onee ,
Topic: Nomenclature Section: 16.2 Difficulty Level: Easy 6. What is the the correct structu structure re for 2+)&imet 2+)&imethylhe4a hylhe4anal' nal' O
O
H
I
II
O
III
O
O
H
I
"( ,( #( D( E( "ns:
I II III I D
H
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Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium -. What is the the correct I! I!"# "# name name for the follo$in% follo$in% compoun&' compoun&' O
"( ,( #( D( E( "ns:
++) ++)Di Dim methy ethyl) l)2) 2)he hept ptan anon onee +)Et +)Ethy hyl)+ l)++ +)& )&im imet ethy hyl)* l)*et ethy hyl)2 l)2)o )oct ctan anone one ++) ++)Di Dim methy ethylc lcy ycloh clohep epttanon anonee ) )Di Dime meth thy ylcyc lcyclo lohe hept ptan anon onee 33) 33)Di Dim methy ethylc lcy ycloh clohep epttanon anonee D
Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium . What is the the correct I! I!"# "# name name for the follo$in% follo$in% compoun&' compoun&' O
"( ,( #( D( E( "ns:
2) 2)&i &im methy ethyl) l)2) 2)pe pent nten enon onee 2+) 2+)&i &im methy ethylc lcyc yclo lope pent nten en)3 )3)o )one ne 2) 2)&i &im methy ethylc lcyc yclo lope pent nt)2 )2)e )eno none ne 3+) 3+)&i &im methy ethylc lcyc yclo lope pent nt)2 )2)e )eno none ne 2)me 2)meth thyl yl)+ )+)m )met ethy hylc lcyc yclo lope pent nt)2 )2)e )eno none ne #
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Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium 7. What is the the correct I! I!"# "# name name for the follo$in% follo$in% compoun&' compoun&'
O
"( ,( #( D( E( "ns:
11 112) 2)Tr Trim imet ethy hyl) l)1 13) 3)he he4e 4eno none ne 12) 12)Di Dim methy ethyl) l)1 13) 3)he he4e 4eno none ne 23) 23)Di Dim methy ethyl) l)1 13) 3)he hept pten enon onee 23) 23)Di Dime meth thy yl)2) l)2)he hept pten en) ))o )one ne +6) +6)Di Dim methy ethyl) l)+) +)he hept pten en) ))o )one ne D
Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium 18. What is the correct structur structuree for 23)&imethyl)2) 23)&imethyl)2)hepten hepten))one ))one'' O
I
O
O
II
III
O
I
O
"( ,( #( D( E( "ns:
I II III I E
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Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium O
11.
" correct name for C 6 H 5 C H 2 C H 2 C H "( 3),en9ylpropanone ,( 3)!henylpropanal #( 3),en9ylpropanal D( Nonanone E( Nonanal "ns: ,
is'
Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium 12. What is the the correct structu structure re for 3)phenylpr 3)phenylpropanal opanal'' O
O H
O
II
I
III O
H O
I
"( ,( #( D( E( "ns:
I II III I E
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Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium 13. What is the correct structur structuree for +)hy&ro4y)2)pheny +)hy&ro4y)2)phenyl)3)he l)3)he4anone' 4anone' O
Ph
Ph
OH
II
I Ph
OH
O
III
OH OH
OH
O
O
H
I
"( ,( #( D( E( "ns:
O
I II III I #
Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium 1. Which is is the proper proper name for for the structur structuree sho$n' C H O
Ph
Ph
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Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium 1+. What is the correct structur structuree for )chloro)3)met )chloro)3)methyl/en hyl/en9al&ehy 9al&ehy&e' &e' O
O
H
O
H
H
Cl
II
I
Cl
Cl O
H H O Cl
Cl
I
"( ,( #( D( E( "ns:
I II III I "
III
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Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium 16. What is the correct correct structure structure for 3)methyl)+)2 3)methyl)+)2+)&i +)&initro nitropheny phenyl(penta l(pentanal' nal' NO2
O
O
H
O2N
NO2
II
I
O
NO2
NO2
O O2N H
O2N H NO2
III
I
O2N
H
O NO2
"( ,( #( D( E( "ns:
I II III I ,
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Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium 1-. What is the correct structure structure for 3)methyl)+)) 3)methyl)+))chloro chloropheny phenyl(he4an l(he4anal' al' O
O
H
Cl
Cl
I
II O
O
H
H
Cl
I Cl
III Cl
O
H
"( ,( #( D( E( "ns:
I II III I D
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Topic: Nomenclature Section: 16.2 Difficulty Level: *e&ium 1. What is the correct correct structure structure for -)/romo)1 -)/romo)1)octy )octyn))one n))one'' Br
Br
Br
O
O
O
II
I
III
Br Br
I
"( ,( #( D( E( "ns:
O
O
I II III I "
Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 17. What is the the correct I! I!"# "# name name for the follo$in% follo$in% compoun&' compoun&' Br
O
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Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 28. What is the the correct I! I!"# "# name name for the follo$in% follo$in% compoun&' compoun&' O
Cl
"( ,( #( D( E( "ns:
H
S( S()3) )3)chl chloro) oro)1) 1)he he4a 4ano none ne S( S()1) )1)chl chloro) oro)3) 3)he he4a 4ano none ne ;() ;()3) 3)ch chlo lorrocy ocycloh clohe4 e4an anon onee S( S()3) )3)chl chloroc orocy ycloh clohe4 e4an anon onee S() S()1) 1)ch chlo loro ro)3 )3)c )cy ycloh clohe4 e4an anon onee D
Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 21.
O
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Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 22. Which is the proper name for the structure structure sho$n' O 2N
O NO2
"( ,( #( D( E( "ns:
3)*e 3)*eth thyl yl)+) )+)1 1) )&i &ini nitr tro/ o/en9 en9yl yl() ()1) 1)pe pent ntan anal al 3)*e 3)*eth thyl yl)1) )1)2 2+) +)&i &ini nitr trop ophen henyl yl()+ ()+)p )pen enta tanal nal 3)*e 3)*eth thyl yl)+) )+)2 2+) +)&i &ini nitr trop ophen henyl yl(p (pent entana anall 3)*e 3)*eth thyl yl)+) )+)2 2+) +)&i &ini nitr trop ophen henyl yl(p (pent entana anal& l&ehy ehy&e &e 3)*e 3)*eth thyl yl)+) )+)2 2+) +)&i &ini nitr trop ophen henyl yl(p (pent ental al&eh &ehy& y&ee #
Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 23. Which is is the proper proper name for for the structur structuree sho$n' O
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Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 2. Which is is the proper proper name for for the structur structuree sho$n /elo$' /elo$' Br O
"( ,( #( D( E( "ns:
-),romo)1 )1)octynal nal -),romo)1 )1)octynon none 2),romo)+ )+-)octynal nal -),r -),rom omo)o)-)m )met ethy hyl)1 l)1)h )hep epty tyne) ne)3) 3)0et 0eton onee -),romo)1) )1)octy ctyn) n))one E
Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 2+. What is the correct structur structuree for ;()-)/romo)1 ;()-)/romo)1)octy )octyn))one' n))one' Br Br
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Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 26. What is the correct structur structuree for S()-)/romo)1) S()-)/romo)1)octyn octyn))one' ))one' Br Br
Br O O
O
II
I
III
Br Br
I
"( ,( #( D( E( "ns:
I II III I #
O
O
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Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 2. Which is the the I!"# I!"# name name for the structure structure sho$n sho$n /elo$' /elo$' H
Br
O
"( ,( #( D( E( "ns:
;() ;()+) +),r ,rom omo) o)2) 2)he hept ptan anal al S( S()+) )+),rom ,romo) o)2) 2)he hept ptan anal al ;() ;()+) +),r ,rom omo) o)2) 2)he hept ptan anon onee S( S()+) )+),rom ,romo) o)2) 2)he hept ptan anon onee ;() ;()3) 3),r ,rom omop open enty tyll meth methyl yl 0eto 0etone ne D
Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 27. What is the correct correct structure structure for ;()+)/r ;()+)/romo)2 omo)2)hepta )heptanone' none' Br
H
Br
H
Br
H
O
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Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 38. What is the correct correct structure structure for S()+)/r S()+)/romo)2) omo)2)heptan heptanone' one' Br
H
Br
Br
H
H
H
O
I
O
II
III
O
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Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 32. What is the correct structure structure for )1)methylcy )1)methylcyclohe4y clohe4yl()2)/ l()2)/utanon utanone' e'
O
II
I
O
III
O
O
O
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Topic: Nomenclature Section: 16.2 Difficulty Level: 5ar& 3. What is the correct structure structure for S())cyclohe4y S())cyclohe4yl)3)me l)3)methyl thyl)2)/uta )2)/utanone' none'
O
II
I
O
I
III
O
O
O
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Topic: ;ea%ents Section: 16. Difficulty Level: Easy 36. Li"l5 L"5( cannot /e use& to convert car/o4ylic aci&s to the correspon&in% al&ehy&es /ecause: "( L"5 L"5 is is not not suff suffic icie ient ntly ly rea react ctiv ive. e. ,( ;#<< ;#<<5 5 is conv conver erte te& & into into ;#<< ;#<
<. "ns: #
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Topic: Topic: ;eaction !ro&ucts Section: 16. an& previous chapters Difficulty Level: *e&ium 3. Select the the structure structure of the maCor maCor pro&uct in in the follo$in% follo$in% reaction. reaction.
i( ,53 )
ii( 52<2<5 52< "( ,( #( D(
Ethyl/en9ene 1)!henylethanol "cetophenone 2)!henylethanal
'
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Topic: Topic: ;eaction !ro&ucts Section: 16. an& previous chapters Difficulty Level: *e&ium 37. Select the the structure structure of the maCor maCor pro&uct in in the follo$in% follo$in% reaction. reaction.
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Topic: Topic: ;eaction !ro&ucts Section: 16. Difficulty Level: *e&ium
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Topic: Synthesis Section: 16. Difficulty Level: *e&ium
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Topic: Synthesis Section: 16. Difficulty Level: *e&ium
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Topic: Synthesis Section: 16. Difficulty Level: *e&ium 3. " %oo& synthe synthesis sis of
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Topic: Topic: ;eaction !ro&ucts Section: 16.+ an& 16.Difficulty Level: 5ar& 76. What $oul& $oul& /e the pro&uct of the the follo$in% follo$in% reaction reaction se@uence' se@uence' OH i( S<#l2 ' ii( #656 "l#l3 O iii( 5S#52#52S5 ,=3 iv( ;aney Ni :52( O
O
OH OH
II
I
I "( ,( #( D( E( "ns:
I II III I E
III
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Topic: Topic: ;eaction !ro&ucts Section: 16.+ an& 16.Difficulty Level: 5ar& 7-. What $oul& $oul& /e the pro&uct of the the follo$in% follo$in% reaction reaction se@uence' se@uence' OH O
i( !#l3 ii( #656 "l#l3 iii( 5S#52#52S5 ,=3 iv( ;aney Ni :5 2(
O
'
OH
II
I
III
OH
I "( ,( #( D( E( "ns:
I II III I ,
Topic: ;ea%ents Section: 16. Difficulty Level: *e&ium 7. Which rea%ent rea%ent $ill not &ifferen &ifferentiate tiate /et$een /et$een 3)/utenal 3)/utenal an& 2)/utanone' 2)/utanone' "( ,r2?##l ,( "%2<<5) #( 52 NN5# NN5#65+ D( *n<<5) E( None of these "ns: #
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Topic: ;ea%ents Section: 16. Difficulty Level: *e&ium 77.
H
H
N N C C 6 H The compoun& C 6 H 5 C /en9al&ehy&e $ith $hich compoun&' "( "mmonia ,( 5y&ra9ine #( Nitro%en D( !henylhy&ra9ine E( 5y&ro4ylamine "ns: ,
5
is pro&uce& /y the reaction of an e4cess of
Topic: Topic: !hysical !roperties ;elationships Stereochemistry Stereochemistry Section: 16. Difficulty Level: *e&ium 188. Stereoisom Stereoisomers ers can e4ist e4ist in the case of $hich $hich of the follo$in%' follo$in%' "( The The hy&r hy&ra9 a9on onee of /ut /utanon anonee ,( The o4ime of acetone #( The The phen pheny ylhy& lhy&ra ra9o 9one ne of of cyc cyclo lohe he4a 4ano none ne D( The cyclic cyclic acetal acetal forme& forme& from from prop propana anall an& an& etha ethane) ne)12) 12)&io &ioll E( The The imi imine of cycl cyclop open enttanon anonee "ns: " Topic: Topic: !hysical !roperties ;elationships Stereochemistry Stereochemistry Section: 16. Difficulty Level: *e&ium 181. Stereoisom Stereoisomers ers can e4ist e4ist in the case of $hich $hich of the follo$in%' follo$in%' "( The The hy&r hy&ra9 a9on onee of /en9 /en9op ophe heno none ne ,( The The o4im o4imee of 2)me 2)meth thy ylcyc lcyclo lope pent ntan anon onee #( The The phe pheny nylh lhy& y&ra9 ra9one one of )me )meth thyl ylcy cycl clohe ohe4an 4anone one D( The The im imine of cycl cyclop open enttanon anonee E( T$o of the a/ove "ns: ,
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Topic: Topic: ;eactions of "l&ehy&es an& etones Section: 16. Difficulty Level: *e&ium 182. Which of the follo$in% follo$in% is forme& forme& $hen 3)methylcy 3)methylcyclopent clopentanone anone reacts reacts $ith hy&ro4ylamine' N-NH-C6H5
I
N-NH2
II
III NO2
O N
I "( ,( #( D( E( "ns:
I II III I #
N H
N-OH
NH2
N
N H
NO2
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Topic: Topic: ;eactions of "l&ehy&es an& etones Section: 16. Difficulty Level: *e&ium 183. Which of the follo$in% follo$in% is forme& $hen )methylpentana )methylpentanall reacts $ith phenylhy&ra phenylhy&ra9ine' 9ine' N-C6H5
N-NH-C6H5
I
II
N-NH2
III
O N
I "( ,( #( D( E( "ns:
I II III I "
N H
N=N-C6H5
NH2
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Topic: Topic: ;eactions of "l&ehy&es an& etones Section: 16. Difficulty Level: *e&ium 18. Which of the follo$in% follo$in% is forme& $hen 223)trimet 223)trimethylcy hylcyclohe4ano clohe4anone ne reacts $ith hy&ro4ylamine' N-NH-C6H5
I
N-NH2
N-OH
III
II
NO2
O N
I "( ,( #( D( E( "ns:
I II III I #
N H
NH2
N
N H
NO2
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Topic: Topic: ;eactions of "l&ehy&es an& etones Section: 16. Difficulty Level: *e&ium 18+. Which of the follo$in% follo$in% is forme& $hen 223)trimet 223)trimethylcy hylcyclohe4ano clohe4anone ne reacts $ith hy&ra9ine' N-NH-C6H5
I
N-NH2
N-OH
II
III NO2
O N
I "( ,( #( D( E( "ns:
I II III I ,
N H
NH2
N
N H
NO2
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Topic: Topic: ;eaction !ro&ucts Section: 16.7 Difficulty Level: *e&ium 186. The pro&uct pro&uct # of the the follo$in% follo$in% reaction reaction se@uence se@uence O C H 3 C C H
F
3
C H
"( C H
,( #(
# N
3
C C O O H
2
#53#52#<<#53 C H 3 C H C H
3
C N
D( #53#5>#5#<<5 E( None of these "ns: "
5 # N
# 5 - N <
5 2< 5 2S < heat
#
$oul& /e:
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Topic: Topic: ;eaction !ro&ucts Section: 16.7 Difficulty Level: *e&ium 18-. The pro&uct pro&uct D of the the follo$in% follo$in% reactio reaction n se@uence O )
#N
5#N
5#l #5- N<
D 52< heat
C H
"( C H
,( #(
3
C C O O H
2
#53#52#<<#53 C H 3 C H C H
3
C N
D( E(
#53#5>#5#<<5 HO
"ns: E
COOH
$oul& /e:
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Topic: Topic: ;eaction !ro&ucts Section: 16.7 Difficulty Level: *e&ium 18. What is the the maCor pro&uct pro&uct of the follo$in% follo$in% reacti reaction on se@uence' 5#N
53
Li"l5
'
O
OH
OH CN
NH2
CN
OH
III
II
I
OH
COOH
"( ,( #( D( E( "ns:
I II III I #
I
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Topic: Topic: ;eaction !ro&ucts Section: 16.7 Difficulty Level: *e&ium 187. What is the the maCor pro&uct pro&uct of the follo$in% follo$in% reacti reaction on se@uence' 5#N
5#l
O
52< heat
OH
OH
OH CN
NH2
CN
OH
III
II
I
OH
COOH
"(
I
I
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Topic: Topic: ;eaction !ro&ucts Section: 16.7 Difficulty Level: *e&ium 118. What is the the maCor pro&uct pro&uct of the follo$in% follo$in% reacti reaction on se@uence' O
5 # N
5 2S <
5 2< heat C N
N O S O 3 H
C N
C O H
H O S O 3 H
C N H
O
I "( ,( #( D( E( "ns:
I II III I ,
II
III
I
2
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Topic: Topic: !hysical !roperties ;elationships Stereochemistry Stereochemistry Section: 16.7 Difficulty Level: *e&ium 111. 111. In $hich of the follo$in% reactions reactions is the final pro&uct e4pecte& to to /e forme& as a racemic mi4ture' H "( # 65 +* % , r
C 6 H 5 C
F
O
O
,( 5 # N
F
C H 3 C C H
3
O
#(
H
F
D(
5#N
H C H 3 C
F
O
4 s # 5 3< 5
F
5 # l
O
E(
C H 3 C H C H 2 C O C 2 H C H
3
5
F i ) , u ( 2 " l 5
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Topic: Topic: ;eaction !ro&ucts Section: 16.7 Difficulty Level: 5ar& 112. What is the the maCor pro&uct pro&uct of the follo$in% follo$in% reacti reaction on se@uence' 52S<
5#N
Li"l5
53
O
52< heat
OH
OH CN
NH2
CN
OH
III
II
I
OH
COOH
"(
I
I
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Topic: Topic: ;eaction !ro&ucts Section: 16.7 Difficulty Level: 5ar& 113. What is the the maCor pro&uct pro&uct of the follo$in% follo$in% reacti reaction on se@uence' 5#N
Li"l5
5#l
53
O
52< heat
OH
OH
OH CN
NH2
CN
OH
III
II
I
OH
COOH
"(
I
I
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Topic: Topic: ;eaction !ro&ucts Section: 16.18 Difficulty Level: *e&ium 11. The pro&uct pro&uct 5 of the the follo$in% follo$in% reactio reaction n se@uence O
# 65 +# 5 2, r
F
$oul& /e: "(
C H
# 65 +(3!
3
C 6 H 5 C H 2 C C 6 H
5
=
# 65 +L i ether
C 6 H 5 C C H
3
5
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Topic: Topic: ;eaction !ro&ucts Section: 16.18 Difficulty Level: *e&ium 11+. What $oul& /e the the final final pro&uct' pro&uct' O
# 5 3I "( ,(
# 65 +(3!
# 65 +L i ether
C 6 H 5 C C H 3 C H
C H
2
C 6 H 5 C C H
3
'
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Topic: Topic: ;eaction !ro&ucts Section: 16.18 Difficulty Level: *e&ium 116. What $oul& /e the the final final pro&uct' pro&uct' O
Na5 #53I
"( ,(
F C 6 H 5 C
!:
C H 3 C 6 H 5
C H
2
'
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Topic: Topic: ;eaction !ro&ucts Section: 16.18 Difficulty Level: *e&ium 11-. What is the the reactant W in the synthesis synthesis %iven %iven /elo$' /elo$'
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Topic: Synthesis Section: 16.18 Difficulty Level: *e&ium 11. Which reacti reaction on se@uence se@uence $oul& /e use& use& to prepare prepare '
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Topic: Synthesis Section: 16.18 Difficulty Level: *e&ium 117. Which Witt Witti% i% rea%ent $oul& $oul& /e use& to synthesi synthesi9e 9e
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Topic: Topic: ;eaction !ro&ucts Section: 16.12 Difficulty Level: *e&ium 121. !re&ict !re&ict the maCor or%anic or%anic pro&uct pro&uct of the follo$in follo$in% % reaction: reaction:
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Topic: Spectroscopy Section: 16.13 Difficulty Level: *e&ium 123. " comp compoun oun& & $ith form formula ula #+518< %ives t$o si%nals only one a triplet an& the other a
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Topic: Spectroscopy Section: 16.13 Difficulty Level: *e&ium 12+. The 15 N*; spectrum of a compoun& $ith formula #-51< %ives t$o si%nals. si%nals. Which
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Topic: Spectroscopy Section: 16.13 Difficulty Level: *e&ium 12. The 15 N*; spectrum of a compoun& $ith formula #-51< %ives a &ou/let at 7.2 ppm.
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