April 20, 2017 | Author: AmanMittal25 | Category: N/A
IIT
TAR.GET
>ilrr
JEE
2OAI
(ALL)
AKO]TTATTC COTIIFOAND,S
ccNrENrs Exercise-I Exercise-II Exercise-III Matrix Exercise-IV-A Exercise-IV-B
2-11 12-13 14-15 16-20 21-25 26-27
AnswerKey
28-32
UBKANT
ACADENTY
(India)privateLimited
fiJehieue J n €-uceAhence
(Raj.) Industrial Area,Kota-324005 A-14(A),RoadNo.1, Indraprastha (07 1, TeL: 44)2423406,320526 3205262Fax: 2423405 Email:
[email protected] Websib: wwwvibrantacademy.com
,
EXErcISE- I e /^.\ How manyn electronare there in the followingspecies: \ I [--ll
(B)4
(A)2
(c)6
andbromide to producecarbocation Easeof ionization
A
(A)Y
(B)
(D)I in? maximum thetreatmentofAg@willbe
(c)
Br
/.-Cl
3.
--sggltt \-/-.,
P ; P rvillbe
(B)(O2sb'6s(c)O
-y
: is themostbasiccompound Whichoneof thefollowing (C)CaHs-N(Cq)2 (B)C6H5-NHCH3 (A)C6Hs-NH2
(D)mixtureof (A)and(B)
(D)C6H5N(C2Hs)2
: cornpounds of thefollowing to rinqmonobrominatiqn reactivitv correctforthede_creasing Whichor.clei.is (il1)c6H6 itv)c6HsNo2 (il)csHscooH (t)c5HscH3 (D)llt > l> ll> lv > (c)li>ll!> lv>l (B) !> lll ll> lv ( A) l > l l > l l l > lv of thefollowing reactivity to ringrnonobromination orderis correctforthedecreasing Whichof thefollowing compounds:
I (A)t> ll > lll > lv
2
€i]-'oo' ,gcooH o]-*o'
II (B)ll> lll>lv> |
III (C)ltlll>ll>lV
IV (D)lit>l>ll>lv
s
ElectrophileNO, attacksthe following:
' (")6.I-*o .'Q)',,,0J-:
..*e ( l v ) l cI \-/
@
InwhichcasesN02 willattackat metaPosition (D)lo n ly (C)lla n dlV (B )l,llandlll ( A)lla n dlV reactionassubstitution forelectrophilic following
(r) (A)i> ll > lll
0l) (B )lll> ll> I
OID ( c) il>lll> |
(D) t> lil > tl
? veof Phenol
Kota(Rai.)Ph.0744'242340o IndustrialArea, Vibrant Academy {I) Pvt. Ltd. "A-14(A)"RoadNo.1,Indraprastha
t2l
Ph
I
+
(A)Ph--FH I Ph Ph
I enfoH 16y
+
Ph
'?c"-' (A)is I I (A), Product "--s ? ") ^ ''. ]
ffiBr
DL ./
Forpreparingmonoalkylbenzene,acylationprocessis preferredthandirectalkylationbecause (B)In alkylation,largeamountof heatis evolved (A) ln alkylation,a poisonousgasis evolved productis formed (D)Alkylationis verycostly (C) In alkylation,pollyalkylated
1f '/ 1b/
,/
AlCl,to givepredominantly: Benzenereactswithn-propylchloridein the presenceof anhydrous (C)3-Propyl-1-chlorobenzene (B) (D)Noreaction (A)n'Propylbenzene lsopropylbenzene
of benzene thegroupof effective wouldbe: andformylation electrophiles lt / -/ Inthesulphonation, acetylation ./
+
''
-
+
+
+
(A)sot,cH3c=o,HCo
^, (B)so3,cH3-c=o,l-{co
(C)SO3,CH3CHO, CO+ HCI pNitrotoluene onfurthernitrationgives:
(D)HSO3,CH3CO,HCO
-Jf
Noz
Noz
Br IndustrialArea, Kota(Raj.)Ph.0744-24234;06 Mbrant Academy (I) Pvt. Ltd.'A-,|4(A}lRoad No.1,lndraprastha
t3t
hereactionis :
T
Y){rlott'i"="offi,"y ocH3
ocH3
y
ocH3
inthereactionis: Themajorproductformed OMe
+ (CHJ,CHCHTBT +
speciesis : theactiveelectrophilic of benzene, In thesulphonation (A) SO2
(c)sol-
(B) SO3
(D)HSO;
bromination of itsaromaticringat thefastestrate? undergoes compounds Whichoneof thefollowing (A)
is: themajorproductformed 21/ ',. Inthereaction L-/ o
J^\ \y
Br,(1more) Fe
o
Br
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t4
-Y
y
HNo3/Hrso!(A)Majorproduct :
MeoAA,, (A)
(B)
(c)
(D) MeO
Not
lncreasing orderof rateof reaction withBry'AlBr, is ' _a^
(D ( A)i l t< t< lt< tv ,o--'/
(m)
(ID
(c ) il < t v < lil < |
(B )lv< lt< l< t v
t'
(IV)
(D)t v < il < ill< |
Whatcombination of acidchlorideor anhydride andarenewouldyouchooseto preparegivencompound ? ./-.
{cF -f
g-cH2{H2-cqH tl
o oo II rflcr Alcl3 ) -13
(B) I ./
o
Whichposition willbe attackedmostrapidlybythenitronium ion(-NOr)*whenthecompound undergoes nitration withHNO./H,SO.:
(A)|
(c)ilr
(D)tv
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t5l
(A)@.-+
ff@I
1sy--0cHcr3,KoH,A+ (c)
(D)Noneoffrese
y
Whichofthefolowing ismostreactive towar@ cl
Qo,r-1
€
O r f d*'-)
t\l
Nq
NO,
ct
tl Y
\ 11 '\ \\:,/ \ ,1'.'
1go\a16"' --) o'?''
\Q
(B) (Major), Product(B) is
cl
cl
{o, (B)
(c) NO,
to/ Y
Hro c6H5cH3 cro'cl" > A >B Thefunctionalgroup presentin B andnameof thereaction wouldbe (A)-cHo, Gattermann aldehyde synthesis (B)-cHo, Etardreaction (C)-COCH3,FriedelCraftsreaction (D)-CHO,Oxoreaction
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3y' r
Whichchloroderivative of benzeneamongthefolloringuouldundergo-hydrolysis mostreadilywithaq.NaOH to furnishtheconesponding hydroxyderivative.
;r (c)nr"rr,r @cr W
. chtorat
conc.H-Sonproduct. Theproduct is: , (B)DDT (C)Tetrlon
@";
(A)Lindane 3gy' \./
-{
AIcl3 > c6HscoNH2 GuHu+A A in theabovereactionis: (A)NH2CONH2 (B)CTCONH2'
.--, (9)
+ cHs-cH2{H24H2-cl
(A)(c|
!^o
(D)Ethaneperchlonate
(c)cH3coNH2
(D)CH2(CDCONH2
(C)Bofrrtheabove
(D)None
Alcl3
> hydrocarbon(X) major productX is:
curcH-cH, I
cHt
CH,
cl4
f
cuHui%a-h-Hees Theendproductintheabovesequenceis: (A)Toluene (B) Ethylbenzene
-{
tol@",
(c) @
cH2cH2cH2cH3
(D)Noneiscorrect
n.ar}. Reactionof SO, is easierin: (A)Benzene y
(B)Toluene
(C)Nitrobenzene
(D)chlorobenzene
lf themixh.rre ofthefolloiving buraomaticcompoundson oxidafonbysfongoxidising (hotKMnOo): agentgives
9Ht
[ 9 ' [9' -A.
cHo
fzHs
-/\
and lO -A-.l
\,/ (B)MixtureofC.H'CHO+c6H5cooH (D)Noneofttreabove Methylgroupattachedto benzenec€rnbe oxidisedto carborylgroupby reactingwith: (A)FerO. (C)KMnOo (D)Cro {ts)AgNO. (A)MixtureofC'H'CHTOH + (C)OnlyC.H'COOH
9H=C*Iz A(Bt2 CCla
Compound Aand B respectively are: (A)o-Bromostyrene, benzoicacid (C)m-Bromosgrene, benzaldehyde
(a)p-U
Thenumberof benzylic hydrogen atomsin ethylbenzene is: (A)3 (B )5 (c)2
benzaldehyde
,benzylacid (D)7
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n
Ye'
11.
F-"-s Productobtainedwhen benzoylacetic acld is heatedwith soda{me is:
tol@cocH3
re)@cooH
ro@cH,
12.
Etardreactionin thefollowingis: (A)OxidationoftoluenetobenzaldehydebychromylcHoride (B)Oxidationof tolueneto benza(ehydeby alkalineKlvlnOl (C) Drydistillation of calciumbenzoate (D) Reactionof benzenewithCl, in thepresenceof UVlight
/li}.
Thehighestyieldof m-productis possiblebytheelectrophilic substitution of thefoltowing:
n
(A)C6H5CH3
(B)C6H5CH2COOC2H5 (D) C6H5C(COOC2HJ3
(c)c6H5cH(cooc2HJ2 ci
4.
'15.
46. 47.
-r
.
LOJ+H2 \,/ :/
Ni,bisht€trp'(A).Whichofthebllouringcanbeisolatedastheproductofthisreaction. : > higbpressure
Whichof theblloMng iJare producedwhena mixhrrcof bemenerapour and o)(ygenis presedoverV.O, catalystat775K? (A) Oxalicacid (B) Gfyoxal (C)Fumaricacid (D)MateicanhydrirJe , Whichof thefollowingis the leastreactivein thecaseof bromination: (A)Phenol (B)Anitine (C) Nitobenzene (D)Anisote Whichof thefollowingis notan aromaticcompound:
.n0
,"O
(c)O A
(A)zn(Hs)+@nc. ncl,Jcl , (.,dct,NaBHo
(D)O
*rrictonrcaction with,B, f"-"
(B)dcl,
OaA
LiAtH.
1o)AAcl,Zn(Hs)+conc.HCl
49.
Ina reaction of cuH5Ythemajorproduct (>60%) is m-isomer, sothegroupy is: (A)-COOH (B)4t (C)-OH (D)+rH2
52.
Whensulphonilicacid(pH,NC6H4SO3H) is treatedwithexcessof bromine,the productis:
product (A)tribromo (C)monobromo product MbrantAcademy(I)Rt
(B)dibromo product (D)tetrabromo product
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53.
Ringnitrationof dimethylbenzeneresultsin theformationof onlyonenitrodimethylbenzene.Thedimethyl benzeneis:
^,D:il] 54.
(D)Noneof these
lf p-methory toluene is nitrated, is: themajorproduct
(D) No reaction
ocHr
ocH3 55.
Anaromaticcompound of molecularformula C.HoBr,wasnitratedwhenthreeisomersof formulaCuH.BrrNO,
wereobtiained. Theoriginalcompound is: (A)odibromobemene (C)pdibromobenzene 56.
ocH3
(B)m{ibomobenzene (D)BothA&C
Whichof thefollowing speciesisexpectedto havemaximumenthalpyinanelectrophilic aromaticsubstitution reaction?
H-.-E&'
X )-+E*+O '.-G (rD (lll) (B)Species 57.
58.
K*
U
(IV) GII) (c) species(lV)
(D)
M
Fortheelectrophilic substitutionreactioninvolvingnitration,whichof thefollowingsequenceregardingthe rateof reactionis true? (A) kcuHot kauout kauru
(B)kcuno kaoou' kaoru '
(C) kcunu= k"oou= k"uru
(D) kcoHot kauoo' kaoru
Fortheelectrophilic substitution reactioninvolvingsulphonation, whichof thefollowingsequenceregarding the rateof reactionis true? (A) kcoHut kauout kauru
(B)kcuHu kauor' kauru '
(c) kconc= k"uou= kauru
(D) kcunu t k"uou' kaoru
Whichof the followingstructures@respondto the productexpected,whenexcessof CuH.reactswith CHrCl,in presence ? of anhydrousAlCl,
cl
cl cl (Raj.)Ph.O7l.l-l24234}o Vibnnt Academy (I) hrt. Ltd.'A-14(A)'RoadNo.1,Indraprastha IndustrialArea, Kotra
tel
reactivityinelectrophi|icsubstitutionreactionsofthefollowingcompounds: ldentifYtheconectorderof
(D (A)l> ll> lll> lv
61.
(B)lv > lll > ll> l
sroupq.^ir1#"llro;r##;r#R'4+'l'-No' ofelectron.withdrawine is: ccnjugation ofthese sroups ii"-"i",
mt"T;fr:fffi"ffi:,;;H;;; o o tl
activates
"t o "activig
I- ' -n-*' J-* (A) -No,>-c=r{,> ogo null
(B)-8 -r'-8-n'i--on (c) 4=N
>4EN'-No'
? ! ^I-*
>-No2> j-H>4-R>-
oao
T
(o)-8-nt-No,
Ii
>-c=N >-e-oRt --[-*
preparegivencompound: Ghoosethebestmethodto
t"Q5\-*o, cHi\- , H'G r--'
(D) aromaticsubstitution' mostreactivetowardsnucreoph*ic compound given forowing the of which
n -W5, (ii)FP
--9+
. {;ff+ ' 'rsvr
t
ffi(1 equivalent)
E(Maio0;Ecanbe:
NO, MbrantAcademyg1il-to-."a.r4(A)..Roadffi'.h'|ndustrialArea,Kotr(Rai.)Ph.o74.242y6
tr0l
Whichis the bestsynthesisof
,o, ./f1\ *^,
\V/
,o, A ,o, V/
,a,, 6 '-'
\\L/
,Nor
Br. ,
H2so4
FcBg
,nvor
)
H2so4
,nqor)
H2so4
tiltor )
)
*nvor H2so4
H2Soa
)
Brz,
FeBg
Br2 ) FcBr3
NaocHr , cH3oH
NaocHr cH3oH
,ovor)
,
, !"T, cH3oH
H2soa
(D) O t r #f f ir f f i 66.
towardnucleophilic Thecumulative effectof theirfluroineactivatethedngsof penh andhexafluorobenzene X is thefollowing Whatis compound synthesis ? aromaticsubstitution.
ffi
(A)-&F-
(x)(cBH4F4o2)
CH = CFI (A)
(A)Statement-1 iscorrect istrueandstrtement-2 explanation forstatement-1. istrue,statement-2 (B)S&atement-l . is NOThe conectexplanation istrueandstatement-2 br statement-1 isfue, statement-2 (G)Statement-1 istalse. istrue,statement-2 (D)Statement-1 istrue. isfalse,statement-2 O 67.
tl
Statement-l : NitrobenzenereactswithMe-C-Cl
. to producem-nitroacetophenone.
Statement-2 NO,groupattachedto theringis a metadirectingduringSr. 68.
Statement-l Rateof nitrationis C.Hr = CeDe- CeTe is ratedetermining stepin nitrationof benzene,notthe Statement-2 Formationof whelandintermediate breakingof C - H or C - D bond.
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nll
1.
catalytic hydroforming: undergoes whenn-octane is obtained Whicharomaticcompound (D)pXylene (C)o-Xylene (B)m-XYlene (A)ethylbenzene
2.
of: acidmaybe preparedby theoxidation Benzoic
(B)
3.
by: canbe prepared lsopropylbenzene + CH3CH= CHr.'..'% (A)Benzene
(B) Benzene+
+ CHfFrcH. (C)Benzene
+ CH.CHzCHTCI (D)Benzene +
-Al\,
#
H"SO.
cl is formed: ln whichof thefollowingreactiont-butylbenzene AlCl, chloride, (A)Benzene+ iso-butyl H"so4 + t-butylalcohol > (C)Benzene
AYct
\2
=at, 4 + (CH.)2C (B)Benzene + (CH3)2 (D)Benzene c= CHz
Alcl3 )
NaoHHzo , product is:
';
(")"o,9
,o,"o@
Whichof thefollowingreactionsof benzeneprovesthepresenceof threecarbon + HCt) (acompound c10H12
*ra$cH2cHzcH24l 3.
compounds withbenzene Givethestructureof theproductexpectedfromthereactionof eachof thefollowing withanswer. bytreatment ofAlCl.,followed of oneequivalent inthepresence
oll
o
tl (A)(cH3)rcH-c*cl isobutyrylehlot'ide ' benzoyl chlorlde
4.
reactions thatcanbe usedto preparethefollowing compound. acylation ShowtwodifferentFriedel-Crafts
CH. 5.
theformulaC'oH,,oO. bywaterto givea ketoneAwith Give reactswithAlCl,followed Thefollowing compound foritsformation. mechanism ofAanda curved-arrow thestructure
o \:/ "."-l-\-cH,cH,_.[.-ct 6.
Predicttheproduct(s) of withacetylchloride inthepresence (a)Friedel-Crafts of oneequivalent acylation of anisole(methoxybenzene) ofAlCl,followedby HrO. withchloromethane in thepresence ofAlClr. (b)Friedel-Crafts of a largeexcessof ethylbenzene alkylation
7.
reaction, acylation asshortmbyhe following example. (phenylbenzene) theFriedel-Grafts undergoes Biphenyi
p-phenylacetophenone
biphenyl
effectof thephenylgroup? Onthebasisof thisresult,whatis thedirecting 8.
productsthatwouldresultfrombromination of eachof thefollowing compounds. Predictthe predominant para your group meta director or a director. reasoning. and explain as an ortho, Classify eachsubstituent
o
tnlGn*-[k,,
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1.
ring. on PhenYl Substituent (A)- CH = CH- CO2H
o tl
(P)o/Pdirectors
(B) -o-S-cH3
(Q)metadirectors
o tl
(c) -NH-c-cH,
group (R)Activating
(D) -s-{H3
group (S)Deactivating
il
o 2.
Matchthefollowing: ColumnI
(A)
(B)
(P) COrtisevolvedfromNaHCOrbythereactionof
nitrosotestis givenby Libbermann
(O)
OH O'IS'A.-.NOr " t C -J
>a Noz
(C)
givesyellowoily Compounds
G)
liquidon reactionwithNaNO,+ HCI H
(D)
evolvea colourlessgas Compounds
(S)
il{c)
on reactionwithactivemetals 3.
Compounds
Substituenton pfienyl
group (P)Activating
(Q)Deactivatinggroup H{H2
(c)
(R)o/p4irector
(S)metadirector
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9.
thenitration whythenitration of anisoleis muchfasterthan underthesameconditions. Explain of thioanisole
9CH. 10.
thioanisole anisole Explainyouranswer. Whichshouldbe faster:brominationof benzeneor brominationof N,Ndimethylaniline?
11.
frombenzene:explainyourreasoning. Outlinea synthesisof m-nitroacetophenone
N,N-dimethylaniline
orN\_ fl fi,i+H. (
\J
12.
m-nitroacetophenone products (if when ethylbenzenereacts under the foltowingconditions. expected any) Give the (c) concd.H2SO4 (b) HNO3,H2SO4r (a) Brrin CClo(dark)
o
il
equiv.),thenHrO (d)C2H5-C-Cl,AlClo(1.1
13.
(ifany)whennitrobenzene reactsunderthefollouing Givetheproducts expected conditions. (a) Cl,FeCl' heat
14.
(b) fumingHNO3,H2SO4
o tl
(c) H.c:C-ct,Atct3(1.1 equiv.),then Flo
theproductof the resulting Whenthefollowing compoundis treatedwithHrSOo, reactionhastheformula product givea curved-arrow Suggest a structure Br, in GClo. for this and does not decolorize and C'uHro for itsformation. mechanism
CHr
15.
(f)Br,FeBr.
(e)CH.Br,AlCl.
HrSe,
z
Writetheprincipal organicproductin eachof thefollowingreactions:
cl (D
2\*o, ttl \-/ I cHl
+ C6H5CH2SK--+A
(i)HNor,Hal9l-,, O
(ii)
(rv)
(ii)NaOCHT,CH3OH
cl
(v) ",Qo.",
(ii)NaSCH3
Noz (vi)
+ cH3cH2oNa+ G
(vii)
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4.
Matchthecolumn: ColumnI
Golumnll
CI (A)
(P)Groupattachedto benzeneringis a +Mgrouphere.
-'\
9j
(B)
(Q)Groupattached to benzeneringis a -M grouphere.
(c)
(R)Electrophile wouldattackon orthoor paraposition.
CH:CH{OOH (D) 5.
(S) Rateof electrophilic substitution is lessthanthat of benzene.
9J
Matchthecolumn:
x
ocH
NO,
NO,
X= halogen
(SNAr). relativereactivigtoward
( B) - C l
(P)312 (o)1
(c)- Br
(R)0.8
(D)-l
(s)-|
( A) . F
6.
Matchtheproductsof following: GolumnI
Columnll
(A)@*.",_@-F (B)
Violetcoloris obtainby the
(o)
@cH2{H
reaction of neutralFeClrwith (C)
Reaction of benzaldehydewith LiAlH4 / HrOgives
Izct (D) lO l+Kl---+? \./
(s)
@tt,-'
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Gomprehension-l(7 to 9) and it follors followingmechanism is an importantreac{ionof aromaticcompounds Electophilicsubstitution RDS .
l+ E 4 -r-o
-#o-' U
(o-comPlex) intermediateof reaction ridrposition.Rateofthisrcactionincreaseswithstabilityofoomplex' IngeneralEoatbcksonmoreelectron ofc-H bondis averyfaststep' thecleavage attiacks, elecffophile wherestnong lnthereaction attack' andectrophilic towards inthJorderof reactivity Anangethefollowing Me OMe cl
7.
v/(II)
(r)
A \y
A v/
(v)
(trD
(A)V'|V>|I|>|l''|(B)|l|>V>|V>||>|(c)ll|>|V>V>lI>|(D)V>lV>I|l>l>l| -r
8.
-
Reaction'lt I O .J* r'r'ot-b
D (A) rater, > r,'
(B) rater,'> rt
(C)ratet,, = r,
(D)r, andrrare notcomParable
I
i
cDr (A) Eoattackspreferablyat-o positionto CH. at+ positiontoCD. (B)Eoattackspreferably position (C) Eocanattiackspreferablyat equallyat anyof the four here. (D)NotPredicable ({0 to 12) Gomprehension'2 Presenceof substitution. are electrophilic Thetypicalreactionof benzeneand otheraromaticcompounds presence of electron while substitution, electrondonatinggroupactivatesthe ringtowardselectrophilic butat thesametimeactivatesthe substitution the ringtowardselectrophilic groupdeactivates withdrawing andallof theseare metiadirecting some groupsare predominantly substitution. ringtowardsnucleophilic g1tups' mostoftheo-andp4irectinggroupsareactivating Excepthalogen, deactivating.
10'
(\
crHrp
v
(A)major.A istrisubstituted ofA is : Thestructure benzene.
CrH.
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n8l
o 1ny-H'sa*(B) + (c) -Qz*Hgrc!+9* g
D andE are:
(B)
(D)
C
c
C C
C
oo
Whichof thefollowing compound is notformed.
(i)NBS,CC|.,hv
1i1ay'FeBr. X represents mixtureof organiccompounds. Themixturedoesnotcontain.
(D)allofthem
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(13to 15) Gomprehenslon€ easyto predictthe positionof attiackon multiplysubstitutedbenzene.lf the benzenering not always It is is not bearsdifferentortho/paradirectinggroupat the 1 and4 positions,the positionof furthersubstitution ln fiactors determine other cases, electronic the outcome. stericeffectsdetermine clear.Sometimes immediately will beat the positionactivatedbythe morestronglyactivatinggroup. further reaction theoutcome,and Somesubstituentsare so stnonglyactivatingthat no catialystis needed,and it is often difficultto top areneededto restrictthereactionto monosubstitution. aftermonosubstfution.Mildconditions substitution (by groups sidechainreaction)so thatreactioncanbestoppedafrer It is possibleto reducetheactivitysuch thenandagainby a sidechainreactiontheoriginalgroupis restored.Effectiveusecan monosubstitution sometimesbemadeof removableblockinggroupsonthering. 13.
Whichof the followingsynthesiscouldbe donein thefirststeP?
CH.
Br
CH.
Br
Whichof thefollowingis the inconectmajorprcduct?
CH.
15.
Whichof thefollowingsidechainreaction/scanbe usedto reducetheactivi$of stronglyactivatinggroups like-4H ? (B)ace$lation (A)benzoylation (D)noneoftheabove (C)bothof heabove
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EXERCISE-/IV(A) ../ 1: ./
O
givespredominantly: Thechlorination of fenicchloride of toluenein presence (A)Benzylchloride (B)m-chlorotoluene (C)Benzalchloride (D)o-andp-chlorotoluene
pEE 19861
Themostbasiccompound amongthefollowing is: (A)Benzylamine (B)Aniline (C)Acetaniline
pEEleeol (D)pnitroanitine
Chlorination of lightandheatfollowedbytreatment of tolueneinthepresence withaqueousNaOHgives: (A)o-cresol (B)p+resol (C)2,4dihydroxytoluene (D) Benzoicacid pEE 19901
3.
pEElse3l
onesgivenbelowfortwo anilinein:
.i(
---*(,j (I)
(ID
(A)ll is notanacceptable structure canonical because carbonium ionsarelessstablethanammonium ions (B)ll is notan acceptable canonical structure becauseit is nonaromatic (C)ll is notan acceptable canonical structure becausethenitrogenhas10valenceelectrons canonical structure . (D)ll is an acceptable Moststablecarbonium ionis:
V
(A)p-NO2-C6H4-*CH, (C)p-Cl-C6H4-*CH2
HEEleesl (B)C6H5*CH2 (D)p-CH3O-C6H4-*CHz
6. / '/
ArrangeinorderofdecreasingtrendtowardsS.reactions: PEE199fl (l)Chlorobenzene (ll)Benzene (lll)Anilinium chloride (lV)Toluene (A )il > t>ilt> tv (B )ilt > l> ll> lv (c )lv > il > l> ilt (D)t > t i> ilt > t v
7.
Amongthefollowing statements on thenitration of aromaticcompounds, thefalseoneis: PEE1994 (A)Therateof benzeneis almostthesameas thatof hexadeuterobenzene (B)Therateof nitration of tolueneis greaterthanthatof benzene. (C)Therateof nitrationof benzeneis greaterthanthatof hexadeuterobenzene (D)Nitration reaction is an electrophilic substitution
v
Nitrobenzene can be preparedfrombenzeneby usinga mixtureof conc.HNO,andconc.HrSOo.In the pEE{ee4 nitrating mixtureHNO,actsas a: (C)Reducing (B)Acid (D)Catalyst (A) Base agent of resonance structure of p-nitrophenoxide ionis: Themostunlikelyrepresentation
/
\frzo-
,y I 11./ r t-
I I
PEE19981
\i,zo
o-oo-o in tolueneracemises of smallamountof slowlyin the presence A solutionof (+)-2-chloro-2-phenylethane of: SbOls, dueto theformation PEE|9991 (C)Free-radical (D)Carbocation (B)Carbene @l Carbanion pEE2000l baseis: Amongstthefollowing thestrongest (B)porNCuH4NH2 (c)m€rNCuH4NH2 (D)c6HscH2NH2 (A)c6HsNH2
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(A)t>lt >lll>lv
(B )tv>ilt>il>t
(D)il> ilt > t > t v
(c )lt > |> ill> t v
pEE2003l
,r,t")*@"r, \-/
(A)ozN@tt,
HzC/
H:c... -lr{g}uoe ,o,
,.,::;)*_@*o,
"r.
NH2
Majorproductof abovereactionis:
(B)
(A)
rc/ \'/
pEE20O4l
acidis hydrolysed withexcessof sodium when4-Methylbenzenesulphonic Wnichof thefollowingisobtrained acetate? PEE200q
1n;cH.{
/L \:/
-+
| CoONa
(B)cH3-O
(cicH3Osolfru +cH3cooH (D)cH3
+sos
Oto2o,
cocHs+ NaoH pEE2004
thestructure is ofthemajorproduct'X'
'nail\o.-",
a
10102N\"
tndustrialArea, Kota(Raj.) Ph.0744-242U06 Vibrant Academy(I) Pvt.Ltd.'A-14(A)"RoadNo.1,Indraprastha
tzzl
',7.
Statement-1: p-Hydroxybenzoic acidhasa lowerboilingpointthano-hydroxybenzoic acid. Statement-2: o-Hydrorybenzoic acidhasintramolecular hydrogen bonding. (A)STATEMENT-1 isTrue,STATEMENT-2 isTrue; STATEMENT-2 isa conectexplanation forSTATEMENT-1 (B) STATEMENT-1 is True,STATEMENT-2 is True ; STATEMENT-2 is NOT a correctexplanation for STATEMENT-1 (C)STATEMENT-1 is False isTrue,STATEMENT-2 (D)STATEMENT-1 isTrue is False,STATEMENT-2 PEE2004
18.
Statement-l: Bromobenzene uponreaction withBr,/ Fegives1,4-dibromobenzene as themajorproduct. Statement-2: In bromobenzene, theinductive effectof thebromogroupis moredominant effect in thanthemesomeric directing theincoming electrophile. (A)STATEMENT-1 isTrue,STATEMENT-2 isTrue; STATEMENT-2 isa conectexplanation forSTATEMENT-1 (B) STATEMENT-1 is True,STATEMENT-2 is True ; STATEMENT-2 is NOT a correctexplanation for STATEMENT-1 (C)STATEMENT-1 isFalse isTrue,STATEMENT-2 (D)STATEMENT-1 isTrue is False,STATEMENT-2 HEE20081
19.
givesa dark withNaNO,/ HCIat0"Cfollowed Statement-l: Anilineon reaction bycoupling withp-naphthol precipitate. bluecoloured formedinthereaction Statement-2 : Thecolourof thecompound of anilinewithNaNO,/ HCIat 0" followed bycoupling withp-naphthol is dueto theextended conjugation. (A)STATEMENT-I isTrue,STATEMENT-2isTrue;STATEMENT-2isacorrectexplanationforSTATE (B) STATEMENT-1 is True,STATEMENT-2 is True ; STATEMENT-2 is NOT a correctexplanation for STATEMENT.l (C)STATEMENT-1 is False isTrue,STATEMENT-2 pEE 20081 (D)STATEMENT-1 isTrue is False,STATEMENT-2
20.
giveninGolumnll. MatcheachofthemmpoundsgiveninColumn{wih thereaction(s), thattheycanundergo, Golumn-l Golumn-ll flT20091
(P) Nucleophilicsubstitution
(O) Elimination
(R) Nucleophilicaddition
(S) Esterification withaceticanhydride
CD Dehydrogenation
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[231
(1) NaOH/tsr,
21. Inthereactior r..$d
T the structureof the productT is.
.NH,
Gv
cH. pEE2olol
{ 1,y
NH
(c) ('
)c pEE20{01
P,Q andS Thecompounds
(o) mixture.Themajorproductformed in eachcase usingHNO./H2SO4 subjectedto nitration wereseparately is respectively,
g-o
NO,
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itcQ: 23.
Whennitlobenzene isfeatedwih Br, in presence of FeBr.themajorproductbrmedis m-bromonitrobemene, pEEree4 Statementswhich are relatedobtainthe m-isomerare: (A)Theelectrondensi$on metacarbonis morethanon orthoand paraposition. (B)Theintermediatecarbonium ionbrmedafterinithlathckofBf athckthemetaposition is leastdestrabilized. (C) Lossof aromaticity whenBf attacksat he orho andp3rapositionsand notat metraposition (D) Easierlossof H'to regionaromatici$formthe metapositionthanftomorthoandparaposition. (CrHrCHrCl)canbe preparcdfromtoluenebychlorination Benzylchlorftle with: (A)SOrClr/hv (c)crrl hv . (B)SOC|2 (D)NaOCl
pEEleoql
'i{
Toluene, whentreated withBrrlFe,givesp-bromotoluene asthemajorprcduct, because theCH,group: (A) is pan directing (B)is metadirecting pEEleeel (C)activatesthe ringby hyperconjugation
Inthereaction
(D)deactivates thering
ilaoH(aqHBr2 ) the intermediate(s) is(are)
pEE2010l
o Br
(c)
(A)
Br
Br Matchthe Golumn n. Column{
Column-ll
(P)
[rT20r0l
Racemicmixture
OH OH
ll (B) H3c*-9-cH,
(O) Additionreaction
tl cH3 cH3
(R) Substitutionreaction
tol.t+cr
Baee)O
(S) Couplingreaction (D Carbocationintermediate
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l20l
EXERCTSE - rV(B) t.
O
acr, >(n) +(cH.)rcH.cH2cl (i)Br".Heat.Lieht
pEEree4 pEElse4l
2,
C.huCrriu
3.
gives (A),CsH6ontreatmentwith dilutesulphuric acidcontaining mercuricsulphate An organiccompound a compound(B),whichcan also be obtainedfroma reactionof benzenewith an acidchloridein the (B),whentreatedwithiodineinaqueousKOH, Thecompound presence chloride. aluminium of anhydrous yields(C) and a yellowcompound(D). ldentify(A),(B),(C) and (D) withjustification. Showhow(B) is pEE1994l (A) formedfrom ?
4.
Toluenereactswithbromineinthepresenceof lightto givebenzylbrominewhilein presenceof FeBr,it gives pEElee6l p-bromotoluene. fortheaboveobservations. Giveexplanation
5.
transformations: Showthestepsto carryoutthefollowing (a) Ethylbenzene-tbenzene (b) --+ 2-phenylpropionic acid Ethylbenzene
6.
C6H.CH2CHCIC6Hs
7.
reactionratherthanthuselectrophilic substitution benzenegiveselectrophilic additionreaction Normally, it hasdoublebonds. although FEE2000l
8.
frombromobenzene in NOTmorethanfivesteps?Stateclearly Howwouldyousynthesis4 methoxyphenol of theintermediate compounds in yoursynthetic thereagentsusedin eachstepandshowthestructures pEE2001l scheme.
9.
in 3 or lesssteps. conversions Carryoutfollowing
(iDNaCN
alcoholktr(oH'heat (A) + (B)
pEEressl
pEEleesl
pEE2003l
10.
AcompoundCaHTO2C|exists in ketoformAandenolicformB. EnolicformB predominates atequilibrium. pEE2003l acidgivesstructures ofAand B. withKMnOogivesm-chlorobenzoic Onoxidation
11.
whereas S-bromo-1,3-cyclopentadiene is ioniccompound, 7-bromo-1, 3, S-cycloheptatriene can'tioniseeven pEE20O4l Explainwhy? thepresence of Ag@,
12.
Givereasons:
(a)
,,,(f.T,
pEE2005l
czH,oH(aq) sorution , acidic H3
tiil r,.O< \:,/
crnros(uq') , neutral
cH.
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(b)
NaoH(aq') t F (tiberated) I
,,,
orrV cHr
n/F ill liiyup\
NaoH(aq') , F is notliberated
cH2NO2 ,()
s1) Noz (cl
Noz
(d)
13.
is formedbutnot
rTiYcH3 NaBr+Mnoz conc'HNo, fBrownfumtt*d)r. ,c(intermediat")V o " D(Explosiveproduct) [pungentsmell ) B andAto C. FindA, B,C andD.AlsowriteequationsAto FEE2(X)51
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azn
r. c
2 .8
3.8
4.D
5.8
6.C
7.8
8,4
9 .D
10. D
11. B
12. C
13. B
14. B
15, A
16. D
17. C
18. D
19. B
20. B
21. D
22. C
23. A
24. B
25. D
26. A
27. D
28. A
A.B
30. B
31. A
32. B
33. B
u .B
35. D
36. B
37. C
38. C
39. D
41. A
42. A
l|3.0
4 .4
45. D
46. C
'S0. C 47. B
49. A
t0. B
51. A
52. A
53. C
54. B
'f8. D 55. B
57. C
58. A
59. D
60. c
61. A
62. B
63. B
u.B
65. A
66. C
67. D
68. A
56. A
EXERCISE.II l. 6. ll. 16.
A ,B,C ,D A,B,C c,D B
2. 7. 12. 17.
A ,B A,B,C B B,C,D
38. 13. 18.
A,C,D A,B,D C c,D
4. 9. 14.
A,B,C,D A,B C
5. 10. 15.
A,B A B,C,D
EXERCISE- III o
(t)rA*
2.
6.
(a)
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t
+ M effectof phenyl
7.
o 8.
ue (o/p)
frt(t'rte).
(C)(meta)
B(c/p) 9. 10.
to 2p3p, thats whyanisoleis morereactivetowards n of 2p-2pin comparison Dueto effectivedelocalizatio nitration. - NMe.groupis + M effectinggrouP
o tl
11.
Ar^, Benzene+ffi
12.
(a)Noreaclion.
SO.H (o/P)
NOr(dp)
Br(c/p)
13.
(C)Noreaction.
(A) NO
cl 14.
Cl 15.
Br
(i)
Noz
,u,''9ot"' cH2scH3
Noz
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Matrix 1.
A-+P,S;
B-+P,R;
C+P,R;
D-+P,S
2.
A-+ Q ; B-+ P,R,S; C + R,S ; D + P,Q,R,S
3.
A-+P,R;
B-+P,R;
C-+P,R;
D-+P,R
4.
A+ P,R,S; B + R ; C -+Q,S ; D+Q,R,S
5.
A-+P;B-+Q;C+R;D-+S
6.
A+P;B+Q;C+R
7. 14"
88.C9.410.A D15.C
11.
B
;D+S,E+T
12.
A
13.
C
EXERCTSE - tV(A) 1 . D 2 . A 3.D 4.C 5.D 6.C
7.C
8 . A 9 . C 10.D 11 .D 12.C13.8
14.
{5-
C
16.
B
17.
18.
D
C
2 0 .( A) - +R Q,T; ( B) - +P ,S ,T; (c) -+ R, S ; (D)+ P 24.
A,C
25 .
A,C
26.
AC
27.
19.
D
21.
C
22.
C
D
A,B
A -R, S ; B -T ; C-P , Q , ; D-R
F,(ERCISE- IV(B) CHTCHT -
1.
[Ottt""'
2.
CHBCHT Br^
lfrl1},|
Q
CHCNCH?
..Ar NacN,
I
2-phenylpropane niitrile
COOK
3.
( c ) l oI
(A)
\-/
4.
whichattacksthe benzeneringat o-,p-position ln presence of FeBr.,Br, producesBf(an electrophile) to givep-bromotoluene. In presence of light,sidechainis attackedto producebenzylbromide.
5.
(a)
(i)C6H'cH(OH)C=CH
H:o'
, C5HrCHGgg ""1 OH;
C.H.CH=CHCHOffi#C.H'CH=C=CH
I
. ott-
C.H'CH=C=CH
OH
(b)
6.
c6HscH2cH2cHctc6H5 -q-t
Soda lime
c.HucH= cHcoHs (Cisandtransforms)
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7.
dueto delocalisation of n-electrons. stabilization Alsocturing hasresonance electrophilic Benzene addition substitution In electrophilic reactionaromaticity is retained. it losesitsaromaticity. reactions, O).Ia
Br 8.
-\
fo l \2
, -., N aoH ,[rrt
or,igr*,.rr*J \2
OMe
.4..' lCl
Me2Soo V,
OMe
c o n c . H, S-\oo nfO]
Na o H, /
so3H
Alternativerout Br -'^'-
I ONa OMe
-A..
lCl
-\ M%so;-pffi# OMe
OMe
HrorIo *-A..l
{2
ONa
OH COOH
COOH
COOF{ 9.
Br
lgj -T-'LQ-[*o.* ----
tlBIi/KHF?
conc.llrsor
,\
-\
OH C=CH{FIO
10.
tol \-r^Cl
(B) Enol conjugation Enolformis morestabledueto extended
otl
c-oH
(A) Moo > -fr to'l
\.^cr
11.
givestropolium ionwhichis aromatic with6r electrons. 7-bromo-1,3,4-cycloheptatriene Onionization Br /.^
I\_:/ i1
(9
'
+Brr
cationwith antiaromatic can'tioniseas itwillinthatcasegivehighlyunstable 5-bromo-1,3-cyclopentadiene 4 r electrons.
Pr e ,A'.
t
t _]) + - u + Br lndustrialArea, Kota(Raj.)Ph.0744-2423406 Mbrant Academy (I) Pvt. Ltd.'A-14(A)" RoadNo.1,Indraprastha
131l
12.
cHs I
dueto partialdoublebondcharacter (a) (i) HrCu - C - OC2H, + HBr(acid) ; (ii)no reaction I CH,
Or-rzort
ttl (b) (i) o2N'-,/
+ F- is liberated mechanism is notpossiblein'(ii)case ; (ii)Bimomecular
cHr (c) (i)dueto presence atomNOgroupis electron of lonepairof nitrogen denating andortho,paradirecting (ii)NO2groupis electronwithdrawing andmetadirecting (d) Dueto reductionof centralring,threefour memberedantiaromatic ringsbecomestablewhileon ringcanbe stabilized. of terminalringonlyoneantiaromatic recuction
13.
(A) H2SO4
(B) Br,
Noz
I
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