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Exercise-I Exercise-II Exercise-III Matrix Exercise-IV-A Exercise-IV-B AnswerKey 2-11 12-13 14-15 16-20 21-25 26-27 28-32
UBKANT
ACADENTY
fiJehieuen -uceAhence J
(Raj.) Industrial Area,Kota-324005 A-14(A),RoadNo.1, Indraprastha (0744)2423406,320526 3205262Fax: 2423405 1, TeL : Email: admin@vibrantacademy.com Websib: wwwvibrantacademy.com
EXErcISE- I
e /^.\ How manyn electronare there in the followingspecies: \ I [--ll
(A)2
(B)4
(c)6
(A) Y
/.-Cl
A
Br
(B)
--sggltt P ; P rvillbe
(c)
3.
\-/-.,
(c)O (B)(O2sb'6s
(D)mixture (A)and(B) of
-y
(D)C6H5N(C2Hs)2
: cornpounds of the to reactivitv rinqmonobrominatiqn following for correct thede_creasing or.clei.is Which (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 the reactivity ringrnonobromination following to for orderis correct thedecreasing of Which thefollowing compounds:
II (B)ll> lll>lv> |
..*e (lv)lc I
\-/
at Inwhich cases N02 willattack metaPosition (D)lo n ly (C)lla n dlV (B )l,llandlll ( A)lla n dlV reaction as substitution for following electrophilic
(r)
(A)i> ll > lll
OID ( c) il>lll> |
? veof Phenol
Ph.0744'242340o Kota IndustrialArea, (Rai.) Indraprastha No.1, Vibrant Academy {I) Pvt. Ltd. "A-14(A)"Road
t2l
Ph
(A)Ph--FH
I Ph Ph
I enfoH 16y
Ph
ffiBr
DL ./
1f '/ 1b/ ,/
process preferred is thandirectalkylation because benzene, acylation monoalkyl Forpreparing (B)In alkylation, gasis evolved largeamount heatis evolved (A) ln alkylation, poisonous of a product formed (D)Alkylation verycostly pollyalkylated is (C) In alkylation, is of in AlCl,to givepredominantly: chloride the presence anhydrous Benzene reacts withn-propyl (B)lsopropylbenzene(C)3-Propyl-1-chlorobenzene Noreaction (D) (A)n'Propylbenzene
be: of the would and of electrophiles lt / -/ Inthesulphonation, acetylation formylation benzene group effective
''
./
(A) sot,cH3c=o,HCo
(C)SO3, CH3CHO, + HCI CO gives: pNitrotoluene further nitration on
(B)^, so3,cH3-c=o,l-{co
(D)HSO3, CH3CO, HCO
-Jf
Noz
Noz
Br
IndustrialArea, (Raj.) Kota Ph.0744-24234;06 lndraprastha Mbrant Academy (I) Pvt. Ltd.'A-,|4(A}lRoad No.1,
t3t
hereaction : is
Y){rlott'i"="offi,"y
ocH3
ocH3
ocH3
+ (CHJ, CHCHTBT +
(c)sol-
(D)HSO;
rate ring bromination itsaromatic at thefastest ? of undergoes compounds Which of thefollowing one (A)
J^\ \y
Br,(1 more) Fe
Br
Ph.0744-2423{;06 IndustrialArea, (Raj.) Kota Indraprastha No.1, Vibrant Academy (I) Pvt. Ltd. "A-14(A)"Road
t4
-Y
MeoAA,,
(A) (B)
(c)
y
(D) MeO
Not
(D
( A)i l t< t< lt< tv ,o--'/
(ID
(m)
(c ) il < t v < lil < |
(IV)
Whatcombination acidchloride anhydride arene of or and you would choose prepare given to compound ?
{cF -f
o oo II rflcr Alcl3 )
-13
tl
./-.
g-cH2{H2-cqH
(B) I
./
Whichposition be attacked will mostrapidly thenitronium (-NOr)*when compound by ion the undergoes nitration HNO./H,SO. with :
(A)|
(c)ilr
(D) tv
t5l
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ff@I
(A)@.-+
(D)Noneof frese
Qo,r-1
t\l
O r f d*'-)
NO,
Nq
ct
tl Y
cl
cl
{o,
(B)
(c)
NO,
to/
Y
Hro c6H5cH3 cro'cl" > A >B Thefunctionalgroup present B andname thereaction in of would be (A)-cHo, Gattermann aldehyde synthesis (B)-cHo, Etard reaction (C)-COCH3, Friedel Crafts reaction (D)-CHO, Oxoreaction
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t6t
3y' r
Which chloroderivativebenzene of among folloringuouldundergo-hydrolysis readily aq.NaOH the most with to furnish conesponding the hydroxy derivative.
;r (c)nr"rr,r @cr
W . chtorat @"; conc.H-Son The is: , product. product (B)DDT (C)Tetrlon
tol@",
!^o
(D)Ethaneperchlonate
(c)cH3coNH2
(D)CH2(CDCONH2
-{
cuHui%a-h-Hees
Theendproduct theabovesequence in is: (A)Toluene (B) Ethylbenzene
.--, (9) + cHs-cH2{H24H2-cl Alcl3
(D)None
-{
(A) (c|
curcH-cH, I
CH,
cHt
(D)None iscorrect (C)Nitrobenzene
(D)chlorobenzene
cl4
(c) @
cH2cH2cH2cH3
\,/ (B)Mixtureof +c6H5cooH C.H'CHO (D)Noneofttreabove groupattached benzene be oxidised carborylgroup reacting Methyl to crn to by with: (A)FerO. (C)KMnOo (D)Cro {ts)AgNO. (A)Mixtureof + C'H'CHTOH (C)OnlyC.H'COOH
[ 9 ' [9'
-A. -/\
9Ht
fzHs
cHo
and -A-. lO l
9H=C*Iz
A(Bt2 CCla
p-U (a)
benzaldehyde
,benzylacid (D)7
ph.Ot4+242g4ff. Vibnnt Academy (I) h,t. L6. "A-14(A]"Road No.1, Indraprastha IndustrialArea, (Raj.) Kote
11.
Ye'
tol@cocH3
12. n
re)@cooH
ro@cH,
Etardreaction thefollowing in is: (A)OxidationoftoluenetobenzaldehydebychromylcHoride (B)Oxidation toluene benza(ehyde alkaline of to by KlvlnOl (C) Drydistillation calcium of benzoate (D) Reaction benzene Cl, in thepresence UVlight of with of yieldof m-product possible theelectrophilic Thehighest is by substitution thefoltowing: of
(A)C6H5CH3 (B)C6H5CH2COOC2H5 (D) C6H5C(COOC2HJ3
ci
/li}.
(c)c6H5cH(cooc2HJ2
4.
-r .
LOJ+H2 \-:/ ,/
'15.
46. 47.
Whichof theblloMng iJare produced whena mixhrrcof bemenerapour and o)(ygen presedoverV.O, is catalyst at775K? (A) Oxalicacid (B) Gfyoxal (C)Fumaricacid (D)MateicanhydrirJe , Whichof thefollowing the leastreactive thecaseof bromination: is in (A)Phenol (B)Anitine (C) Nitobenzene (D)Anisote Whichof thefollowing notan aromatic is compound:
.n0
,"O
(c)O
A dcl, (B)
(D)O
OaA
LiAtH.
1o)AAcl,Zn(Hs)+conc.HCl
y Ina reaction cuH5Y major product of (>60%) m-isomer, thegroup is: the is so (A)-COOH (B)4t (C)-OH (D)+rH2
52.
53.
Ringnitration dimethyl of benzene results theformation onlyonenitrodimethyl in of benzene. dimethyl The benzene is:
^,D:il]
54. product lf p-methory toluene nitrated, major is is: the
(D)None these of
(D) No reaction
ocH3
55.
ocHr
ocH3
Anaromatic compound molecularformula was of C.HoBr, nitrated whenthree isomers formula of CuH.BrrNO,
(B)m{ibomobenzene (D)BothA& C
Which thefollowing of species expected havemaximum is to enthalpy anelectrophilic in aromatic substitution reaction?
H-.-E&'
K*
(D)
Fortheelectrophilic nitration, reaction involving substitution whichof thefollowing regarding the sequence rateof reaction true? is t (A) kcuHot kauou kauru
Fortheelectrophilic substitution reaction involving sulphonation, whichof thefollowing sequence regarding the rateof reaction true? is t (A) kcoHut kauou kauru
Whichof the following structures @respondto the product expected, whenexcessof CuH.reactswith CHrCl, presence anhydrousAlCl, in ? of
cl
cl cl
Vibnnt Academy (I) hrt. Ltd.'A-14(A)'Road IndustrialArea, (Raj.) No.1, Indraprastha Kotra Ph.O7l.l-l24234}o
tel
(D
(A)l> ll> lll> lv (B)lv > lll > ll> l
61.
activates
fffi"ffi:,;;H;;; mt"T;fr: o o tl
ogo null
"t"activig o
>4EN'-No'
>-No2> j-H>4-R>-
? ! ^I-*
Ii
t"Q5\-*o, cHi\- ,
H'G r--'
oao
(o)-8-nt-No,
n -W5, (ii)FP
--9+
ffi equivalent) (1
E(Maio0;Ecanbe:
NO, MbrantAcademyg1il-to-."a.r4(A)..Roadffi'.h'|ndustrialArea,Kotr(Rai.)Ph.o74.242y6
tr0l
,o, ./f1\
*^, \V/
FcBg
Br. ,
,Nor
H2so4
H2Soa
tiltor )
NaocHr ,
cH3oH
,o, A ,o, V/
,nvor H2so4
*nvor H2so4
Br2 ) FcBr3
NaocHr cH3oH
,a,, 6
'-' \\L/
H2so4
,nqor)
FeBg
Brz,
H2soa
,ovor)
!"T, , cH3oH
(D) O t r #f f ir f f i
66. the nucleophilic activate dngsof penh andhexafluorobenzene toward Thecumulative effectof theirfluroine X Whatis compound is thefollowing synthesis ? substitution. aromatic
ffi
CH = CFI (A)
(A)-&F-
(x)(cBH4F4o2)
(A)Statement-1 statement-2 andstrtement-2correct is istrue explanation statement-1. for istrue, (B)S&atement-l statement-2 andstatement-2NOT conect . is istrue he explanation statement-1 br isfue, (G)Statement-1 is istrue, statement-2talse. (D)Statement-1 is statement-2true. isfalse, O
67. reactswithMe-C-Cl Statement-l : Nitrobenzene
tl
. to produce m-nitroacetophenone.
to during Sr. Statement-2 NO,groupattached theringis a metadirecting 68. is Statement-l Rateof nitration C.Hr = CeDe CeTe not is of intermediate ratedetermining in nitration benzene, the step of Statement-2 Formation wheland breaking C - H or C - D bond. of
IndustrialArea, (Raj.) Ph.074-242U06 Kota No.l,Indraprastha Vibrant Academy (I) hrt L6.'A-14(A)" Road
nll
1. 2.
catalytic hydroforming: undergoes whenn-octane is compound obtained aromatic Which (D)pXylene (C)o-Xylene (B)m-XYlene (A)ethylbenzene of: by acid Benzoic maybe prepared theoxidation
(B)
3.
H"SO.
+ (C)BenzeneCHfFrcH. cl
-Al\,
+ (D)BenzeneCH.CHzCHTCI +
is t-butylbenzeneformed: reaction ln whichof thefollowing + AlCl, chloride, (A)Benzene iso-butyl H"so4 + > (C)Benzene t-butylalcohol
AYct
\2
';
(")"o,9
,o,"o@
double bondsin it: proves presence threecarbon<arbon of the of reactions benzene Whichof thefollowing (A)Formation atriozonide of to (B)Hydrogenation benzene cyclohexane of of by (C)Formation CuHuClu addition chlorine of acid nitdc of with benzene a mixture concentrated acidandsulphuric on (D)Formation nitrobenzene heating of 7. in Electrophile NOf aftacksthe following whichcasesNOf willbeat metaposition:
(D) withthe about by atomin benzene alkylgroupcanbe brought of of Thereaction replacement a hydrogen reagents: following (B)Alkene andAlCl. (A)Alkylchloride AlCl, and (D)Alkanoland acid (C)Alkanoland alkali is statements conect: of Which thefollowing faster thanthatof benzene (A)Bromination toluene occurs of thanthatof ethylbenzene (B)Nitration toluene faster is of (C)Thebromonium isa goodnucleophile ion ion (D)Effective is nitrating agent nitrate
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(A) -l "v[l
.A\
X (B) I li
\2
(B)CH,=Q11 C;
(c)cH3cH2cl
(D)CH,=Q11-CH2{;
cl
(D)C6H6. /\ ' Alcls
14.
(D)-N =C
is: water with derivative treatment brohine on a that of Thestructure thecompound grves tribromo
cooH
A,.o ,o,LgJ
OH OH
group is activating the the Amongst following, moderately (c)-Nq (B)-NHCOCH3 (A)-NHR 17.
(D)--CH3
is statement / are : False reaction' not addition normallydoes undergo it bonds, three (A)Although contains double benzene of isan (B)m+hlorobromobenzeneisomer m-brcmochlorobenzene' p for three orbitals hybridization. uses (C)Inbenzene, carbon allthe position. goup electrophilic tothemeta the orients incoming in substituentbenzene (D)An electron donating ftom product obtained is )R themeta-substituted
(A)PhSR
(B)PhsR
tl o
o ll (c)P hSR tl o
(D)Ph-S-OR
3
o
ll
trEl
EXERCISE- TII
1. 2. isadded a large to excess benzene of is when2-methylpropene containing andthe HF Whatproduct formed ? is whatmechanism it formed Lewis acidBF.?By mechanism itsformation and for reaction givethecurved-arrow . (Hint: of Predict product thefollowing the can alkylations be usedto formrings.) Friedel-Grafb
*ra$cH2cHzcH24l
3.
of from compounds benzene with expected thereaction eachof thefollowing of Givethestructure theproduct followed treatment answer. with by of of inthepresence oneequivalent AlCl.,
tl (A)(cH3)rcH-c*cl
isobutyrylehlot'ide ' benzoyl chlorlde
o ll
4.
reactions canbe used prepare following that to the compound. acylation Friedel-Crafts Show different two
CH. 5. to the bywater givea ketoneAwith formula C'oH,,oO. Give reacts AlCl,followed with Thefollowing compound for mechanism itsformation. ofAanda curved-arrow thestructure
o
\:/ "."-l-\-cH,cH,_.[.-ct 6. Predict product(s) the of (methoxybenzene) acetylchloride thepresence oneequivalent with in (a)Friedel-Crafts of acylation anisole of by ofAlCl,followed HrO. with in of (b)Friedel-Crafts of of excess ethylbenzene chloromethanethepresence AlClr. alkylation a large reaction, shortm he following acylation as example. (phenylbenzene) by the undergoes Friedel-Grafts Biphenyi
7.
biphenyl
p-phenylacetophenone
group? effect thephenyl of whatis thedirecting Onthebasis thisresult, of 8. products wouldresult frombromination eachof thefollowing of compounds. Predict predominant the that paradirector a metadirector. explain yourreasoning. groupas an ortho, or and Classify eachsubstituent
tnlGn*-[k,,
lndustrialArea, (Raj.)Ph.0744-242U6 Kota Mbrant Academy (I) R/t Ld. 'A-14(A)" RoadNo.l, Indraprastha
tf 4l
1.
(P)o/Pdirectors (Q)metadirectors
o tl
(c) -NH-c-cH,
(D) -s-{H3
o tl
o
2. the Match following: ColumnI
il
(A)
(B)
(O)
>a
Noz
(C)
G)
H
(D)
(S)
il{c)
3.
Compounds
Substituenton pfienyl
group (P)Activating
(Q)Deactivatinggroup
H{H2
(c)
(R)o/p4irector
(S)metadirector
Kotra Ph.074'24234;C6, IndustrialArea, (Raj.) Indraprastha No.1, Road Mbrant Academy (I) hrt Ltd. "A-14(A)"
tf 6l
9.
fasterthan nitration thioanisole the is whythe of underthe same Explain nitration anisole much of conditions.
9CH.
10.
thioanisole anisole youranswer. or of of Explain Whichshouldbe faster:bromination benzene bromination N,Ndimethylaniline?
N,N-dimethylaniline
11.
orN\_ fl fi,i+H. (
\J
12.
m-nitroacetophenone productsexpected (if any)when ethylbenzene reacts under the foltowingconditions. Give the (c) concd.H2SO4 (b) HNO3,H2SO4r (a) Brrin CClo(dark)
o
13.
equiv.),thenHrO (d)C2H5-C-Cl,AlClo(1.1
il
(e)CH.Br,AlCl.
(f)Br,FeBr.
(if reacts when nitrobenzene under follouing the Give products the expected any) conditions.
(a) Cl,FeCl' heat (b) fumingHNO3, H2SO4
o tl
14.
is with the Whenthefollowing compound treated HrSOo, product the resulting of has reaction theformula Suggest structure thisproduct givea curved-arrow a Br, for anddoesnotdecolorize in GClo. and C'uHro for mechanism itsformation.
CHr
HrSe,
15.
cl
(D
2\*o, ttl
\-/ I cHl
+ C6H5CH2SK--+A
(ii)
(ii)NaOCHT,CH3OH
(i)HNor,Hal9l-,, O
(rv)
cl
(v) ",Qo.",
Noz
(vi)
(ii)NaSCH3
+ cH3cH2oNa+ G
(vii)
tl5l
4.
Golumnll
CI
(A)
-'\
9j
(B)
(c)
CH:CH{OOH
(D) 5.
9J
x
ocH
NO,
NO,
X= halogen ( A) . F ( B) - C l
(P)312 (o)1
(R)0.8
(c)- Br
(D)-l 6. Match products following: the of Golumn I
(s)|
Columnll
(A)@*.",_@-F
(B) Violet coloris obtain the by reaction neutral FeClrwith of (C) Reaction benzaldehydewith of LiAlH4HrOgives /
(o)
@cH2{H
(s)
@tt,-'
t14
IndustrialArea, (Raj.) Kota Mbrant Acaderry (I) hlt L6.'A-14(Al" Road No.l,lndraprastha P\.O74-242Y6
(7 Gomprehension-l to 9) mechanism and compounds it follors following of reac{ion aromatic is substitution an important Electophilic
l+ E 4 -r-o RDS .
7.
(o-comPlex) of intermediate reaction ridrposition.Rateofthisrcactionincreaseswithstabilityofoomplex' IngeneralEoatbcksonmoreelectron is of the attiacks, cleavage c-H bond averyfaststep' elecffophile stnong where lnthereaction attack' an towards dectrophilic of in the Anange following thJorder reactivity Me OMe cl
-#o-' U
A \y
(trD
(r)
-r -
v/ (II)
A v/
(v)
(A)V'|V>|I|>|l''|(B)|l|>V>|V>||>|(c)ll|>|V>V>lI>|(D)V>lV>I|l>l>l|
8.
* Reaction'lt I O .J r'r'ot-b
D
(A) rater, > r,'
(B) rater,'> rt
(C)ratet,, = r,
cDr
to preferably at-o position CH. (A) Eoattacks CD. preferably at+ positionto (B)Eoattacks at preferably equally anyof the fourposition at (C) Eocanattiacks here. (D)NotPredicable ({0 Gomprehension'2 to 12) of Presence substitution. are compounds electrophilic and of Thetypicalreaction benzene otheraromatic presence electron of while substitution, the groupactivates ringtowardselectrophilic donating electron the butat thesametimeactivates substitution electrophilic the groupdeactivates ringtowards withdrawing theseare and metiadirecting allof are some groups predominantly substitution. nucleophilic ringtowards g1tups' groupsare activating p4irecting mostoftheo-and halogen, Except deactivating.
10'
(\
crHrp
v
CrH.
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n8l
o
1ny-H'sa*(B) + (c) -Qz*Hgrc!+9* g
D andE are:
(B)
C C
(D)
oo
(i)NBS,CC|.,hv
1i1ay'FeBr.
X represents mixture organic of compounds. mixture The doesnotcontain.
(D)allofthem
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lrel
(13 Gomprehenslon to 15) ring substituted lf benzene. the benzene on of not alwayseasyto predictthe position attiack multiply It is positions, position furthersubstitution not is groupat the 1 and4 the of directing ortho/para bearsdifferent ln fiactors determine cases, electronic theoutcome. other determine effects steric clear. immediately Sometimes group. activated the morestrongly by activating will furtherreaction beat the position and theoutcome, is that no catialyst needed,and it is often difficultto top activating are Somesubstituents so stnongly to the to are Mild after substitution monosubstfution. conditions needed restrict reaction monosubstitution. (by afrer groups sidechainreaction) thatreaction bestopped so can such the to It is possible reduce activity groupis restored. Effective can use the then monosubstitution andagainby a sidechainreaction original groups thering. on blocking be sometimes madeof removable 13. couldbe donein thefirststeP? synthesis Whichof the following
CH.
Br
CH.
? majorprcduct is Whichof thefollowing the inconect
Br
CH.
15.
groups the activating can Whichof thefollowing chainreaction/s be usedto reduce activi$of strongly side like-4H ? (B)ace$lation (A)benzoylation (D)noneof theabove (C)both heabove of
Kota Ph.074-24234;06, IndustrlalArea, (Raj.) Indraprastha No.1, Mbrant Academy (I) Pvt. Ltd.'A-14(A)"Road
l20l
EXERCISE-/IV(A)
../ 1: ./ gives predominantly: Thechlorination toluene presence fenicchloride in of of (A)Benzyl (B)m-chlorotoluene chloride (C)Benzalchloride (D)o-and p-chlorotoluene Themostbasic among following compound the is: (A)Benzylamine (B)Aniline (C)Acetaniline pEE 19861
O 3.
pEEleeol
(D)pnitroanitine
Chlorinationtoluene thepresence light heat in of of and gives: followed treatment aqueous by with NaOH (A)o-cresol (B)p+resol (C)2,4dihydroxytoluene Benzoic pEE 19901 (D) acid given ones belowfortwo aniline in:
pEElse3l
---*(,j
(I)
.i(
(ID
(A)ll is notanacceptable structure canonical because carbonium arelessstable ions ions thanammonium (B)ll is notan acceptable canonical structure because is nonaromatic it (C)ll is notan acceptable canonical structure because nitrogen 10valence the has electrons canonical structure . (D)ll is an acceptable V Moststable carbonium is: ion
(A)p-NO2-C6H4-*CH, (C)p-Cl-C6H4-*CH2 (B)C6H5*CH2 (D)p-CH3O-C6H4-*CHz
HEEleesl
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 Among following statements thenitration aromatic on of the compounds, falseoneis: PEE1994 the (A)Therateof benzene almost sameas thatof hexadeuterobenzene is the (B)Therateof nitration toluene greater is thanthatof benzene. of (C)Therateof nitration benzene greater is thanthatof hexadeuterobenzene of (D)Nitration an electrophilic reaction is substitution In Nitrobenzene be prepared frombenzene using mixture conc.HNO,andconc.HrSOo. the by can a of pEE{ee4 nitrating mixture HNO,actsas a: (C)Reducing (B)Acid (D)Catalyst (A) Base agent representationresonance of structure p-nitrophenoxide is: of ion Themostunlikely PEE19981
7.
v
/
\frzo-
\i,zo
,y
I 11./ r
t-
o-oo-o
of in toluene racemises of slowly the presence smallamount in A solution (+)-2-chloro-2-phenylethane of of: SbOls, to theformation due PEE|9991 (C)Free-radical (D)Carbocation (B)Carbene @l Carbanion pEE2000l baseis: Amongst following strongest the the (B)porNCuH4NH2 (c)mrNCuH4NH2 (D)c6HscH2NH2 (A)c6HsNH2
l2rl
No.l,Indraprastha Kota Ph.0744-2123!;06 IndustrialArea, (Raj.) tbrant Academy (I) Rrt. L6.'A-14(A)" Road
I
I
(A)t>lt >lll>lv
(B )tv>ilt>il>t
pEE2003l
(A)ozN@tt,
,r,t")*@"r, \-/
HzC/
,.,::;)*_@*o,
NH2
pEE20O4l
(A)
(B)
rc/ \'/
acid with of is when4-Methylbenzenesulphonic is hydrolysed excess sodium Wnich thefollowing obtrained of acetate? PEE200q
cH.{ 1n;
/L
\:/
| CoONa
-+
(B) -O cH3
+sos
cocHs+ NaoH
pEE2004
Oto2o,
'nail\o.-",
10102N\"
a
tzzl
tndustrialArea, (Raj.) Kota Ph.0744-242U06 Indraprastha Road No.1, Vibrant Academy(I) Pvt.Ltd.'A-14(A)"
',7.
Statement-1 p-Hydroxybenzoic hasa lower : acid point boiling thano-hydroxybenzoic acid. Statement-2 o-Hydrorybenzoic hasintramolecular : acid hydrogen bonding. (A)STATEMENT-1 isTrue, isTrue; STATEMENT-2 conect STATEMENT-2 isa explanation STATEMENT-1 for (B) STATEMENT-1True,STATEMENT-2True ; STATEMENT-2 NOT a correct is is is for explanation STATEMENT-1 (C)STATEMENT-1 is False isTrue, STATEMENT-2 (D)STATEMENT-1 isTrue is False, STATEMENT-2 PEE2004 Statement-l: Bromobenzene reaction Br,/ Fegives1,4-dibromobenzene upon with as themajorproduct. group moredominant Statement-2 In bromobenzene, inductive : the effect thebromo of is effect directing incoming in thanthemesomeric the electrophile. (A)STATEMENT-1 isTrue, isTrue; STATEMENT-2 conect STATEMENT-2 isa explanation STATEMENT-1 for (B) STATEMENT-1True,STATEMENT-2True ; STATEMENT-2 NOT a correct is is is for explanation STATEMENT-1 (C)STATEMENT-1 isFalse isTrue, STATEMENT-2 (D)STATEMENT-1 isTrue is False, STATEMENT-2 HEE20081
18.
19.
gives with / Statement-l Aniline reaction NaNO, HCIat0"Cfollowed coupling p-naphthol a dark : on by with precipitate. bluecoloured formed thereaction aniline NaNO, HCIat 0" followed of Statement-2Thecolour thecompound : in with / of bycoupling p-naphthol dueto theextended with is conjugation. (A)STATEMENT-I isTrue,STATEMENT-2isTrue;STATEMENT-2isacorrectexplanationforSTATE (B) STATEMENT-1True,STATEMENT-2True ; STATEMENT-2 NOT a correct is is is for explanation STATEMENT.l (C)STATEMENT-1 is False isTrue, STATEMENT-2 pEE 20081 (D)STATEMENT-1 isTrue is False, STATEMENT-2 given Column{wih thereaction(s), theycanundergo, in given Golumnll. Match each themmpounds of that in Golumn-l Golumn-ll flT20091
20.
(P) Nucleophilicsubstitution
(O) Elimination
(R) Nucleophilicaddition
CD Dehydrogenation
No.1, Indraprastha IndustrialArea, (Raj.) Ph.0744-2423406 Mbrant Academy (I) Pvt. Ltd. "A-f 4(A)" Road Kota
[231
(1) NaOH/tsr,
.NH,
Gv
{
1, y
cH. pEE2olol
NH
(c)
('
)c
pEE20{01
P, Thecompounds Q andS
(o)
mixture.Themajorproductformed eachcase in HNO./H2SO4 using subjected nitration wereseparately to is respectively,
g-o
NO,
(Raj.) Kota Indraprastha'lndustrialArea, Ph.074-242U06 No.1, Road Vibrant Academy (I) Pvt. Ltd. "A-14(A)u
a?4'l
itcQ: 23.
product Whennitlobenzenefeatedwih Br, in presence FeBr. major is of the brmedis m-bromonitrobemene, pEEree4 Statementswhich related are obtain m-isomerare: the (A)Theelectron densi$on metacarbonis morethanon orthoand paraposition. (B)Theintermediatecarbonium ionbrmedafterinithlathckof athckthemetaposition leastdestrabilized. Bf is (C) Lossof aromaticity position whenBf attacks he orho andp3rapositions notat metra at and (D) Easier lossof H'to regionaromatici$ formthe metaposition thanftomorthoandparaposition. (CrHrCHrCl) be preparcd fromtoluene chlorination Benzylchlorftle can by with: (A)SOrClr/hv (c)crrl hv . (B)SOC|2 (D)NaOCl
'i{
pEEleoql
gives p-bromotoluene major prcduct, Toluene, treated BrrlFe, when with asthe because CH,group: the (A) is pan directing (B)is meta pEEleeel directing
(C)activates ringby hyperconjugation the (D)deactivates ring the
Inthereaction
pEE2010l
o
Br
(A)
(c)
Br Br
Column-ll
[rT20r0l
(P)
OH OH
Racemicmixture
ll (B) H3c*-9-cH,
tl cH3 cH3
(R) Substitutionreaction
tol.t+cr
Baee)O
l20l
EXERCTSE rV(B) t.
2, 3.
pEEree4
pEElse4l
C.huCrriu
(iDNaCN
sulphuric containing gives (A), dilute acid mercuric on sulphate compound CsH6 treatmentwith An organic froma reaction benzene of with an acidchloride the (B), in a compound whichcan also be obtained (B),whentreated iodine aqueous The with presence anhydrous chloride. compound in KOH, aluminium of (A), (D). ldentify (B),(C) and (D) withjustification. yields(C) and a yellow compound Showhow(B) is pEE1994l (A)? from formed of bromine whilein presence FeBr,it gives in with of reacts bromine thepresence lightto givebenzyl Toluene pEElee6l p-bromotoluene. explanation theabove for observations. Give transformations: out to Show steps carry thefollowing the (a) Ethylbenzene-tbenzene (b) --+ acid Ethylbenzene 2-phenylpropionic
C6H.CH2CHCIC6Hs alcoholktr(oH'heat (A) + (B)
4. 5.
pEEressl
6.
pEEleesl
7. 8.
giveselectrophilic rather reaction thanthuselectrophilic substitution benzene addition reaction Normally, it bonds. although hasdouble FEE2000l from in 4 State clearly Howwouldyousynthesis methoxyphenol bromobenzene NOTmorethanfivesteps? of usedin eachstepandshowthestructures theintermediate compounds yoursynthetic in thereagents pEE2001l scheme. in conversions 3 or lesssteps. Carry following out
9.
pEE2003l
10.
formB. Enolic enolic formB predominates Acompound in keto CaHTO2C|exists formAand atequilibrium. pEE2003l givesm-chlorobenzoic givesstructures Aand B. acid of with Onoxidation KMnOo whereas S-bromo-1,3-cyclopentadiene is ionic ionise even 7-bromo-1, S-cycloheptatriene compound, 3, can't pEE20O4l why? Explain thepresence Ag@, of Givereasons:
11.
12.
pEE2005l
(a)
,,,(f.T,
tiil r,.O< \:,/
crnros(uq') , neutral
(b)
,,,
NaoH(aq') (tiberated) t F
I
orrV cHr
n/F
ill liiyup\
cH2NO2
NaoH(aq')F is notliberated ,
s1)
Noz (cl
,()
Noz
(d)
13.
rTiYcH3 NaBr+Mnoz conc'HNo, V fBrownfumtt*d)r. ,c(intermediat") o " D(Explosiveproduct) [pungentsmell ) Ato B write equationsAtoand C. Find B,C andD.Also A, FEE2(X)51
IndustrialArea, (Raj.) Kota Ph.0744-242Y06 No.1, Indraprastha Vibrant Academy (I) P\rt. Ltd.'A-14(A)" Road
azn
r. c
8,4 15, A 22. C A.B 36. B
l|3.0
3.8 10. D 17. C 24. B 31. A 38. C 45. D 52. A 59. D 66. C
4.D 11. B 18. D 25. D 32. B 39. D 46. C 53. C 60. c 67. D
5.8 12. C 19. B 26. A 33. B 'S0. C 47. B 54. B 61. A 68. A
u .B
41. A 'f8. D 55. B 62. B
t0. B 57. C
u.B
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 -
2.
(t)rA*
6.
(a)
IndustrialArea, (Raj.)Ph.0744-2423400 Kota Vf brant Academy (I) h/t. Ltd. 'A-14(A)" RoadNo.1,Indraprastha
t28l
7.
+ M effectof phenyl
o
8.
(C)(meta)
frt(t'rte).
ue (o/p)
B(c/p)
9. 10.
towards is to in n delocalizatioof 2p-2p comparison 2p3p, thats whyanisole morereactive Dueto effective nitration. grouP is - NMe.group + M effecting
11.
Ar^, Benzene+ffi
o tl
12.
(a)Noreaclion.
NOr(dp)
SO.H (o/P)
Br(c/p)
13.
(A)
(C)Noreaction.
cl
14.
NO
Cl 15. (i)
Br
Noz
,u,''9ot"' cH2scH3
Noz
l2el
Ph.07+21234;06 Kota IndustrialArea, (Rai.) lndraprastha No.1, Road Mbrant Acadenry(I) hrt LH. "A-14(A)"
Matrix
1. 3. 5. 7. 14"
A-+P,S; A-+P,R; B-+P,R; B-+P,R; C+P,R; C-+P,R; D-+P,S D-+P,R 2. 4. 6. A-+ Q ; B-+ P,R,S C + R,S ; D + P,Q,R,S ; A+ P,R,S B + R ; C -+Q,S ; D+Q,R,S ; A+P;B+Q;C+R 11. B 12. A ;D+S,E+T 13. C
EXERCTSEtV(A) 1 . D 2 . A 3.D 4.C 5.D 6.C 8 . A 9 . C 10.D 11 .D 12.C13.8 {5C 16. B 17. D 18. C 19. 21. D C 22. C A,B 7.C 14. D
1.
[Ottt""'
2.
lfrl1},|
COOK
..Ar NacN,
CHCNCH?
2-phenylpropaneitrile ni
3.
(A)
(c)lo I
\-/
4.
whichattacks benzene at o-,p-position ln presence FeBr.,Br, produces of Bf(an electrophile) the ring to givep-bromotoluene.presence light, is In of sidechain attacked produce to benzyl bromide.
(a)
5.
(i)C6H'cH(OH)C=CH
H:o'
C.H.CH=CHCHOffi#C.H'CH=C=CH OH
Soda lime
. ott-
C.H'CH=C=CH
(b)
6.
c6HscH2cH2cHctc6H5 -q-t
IndustrialArea, (Raj.) Kota No.1, Indraprastha Ph.0744-2423406 Vibrant Academy (I) Pvt. Ltd. "A-14(A)"Road
7.
due of stabilization to delocalisationn-electrons. cturing Also has electrophilic Benzene resonance addition substitution In reaction aromaticity retained. is it reactions, losesitsaromaticity. electrophilic Br
8.
fo l \2
-\
or,igr*,.rr*J \2
O).Ia
Me2Soo V,
.4..' lCl
OMe
OMe
c o n c . H, S o o n-\-] fO so3H
Na o H, /
I ONa
OMe OMe
-A..
lCl
ONa COOF{ 9.
,\
HrorIo l *-A..
{2
OH COOH COOH
tlBIi/KHF?
OH C=CH{FIO
10.
tol
\-r^Cl
o tl
c-oH
\.^cr
gives tropolium whichis aromatic 6r electrons. ion with 7-bromo-1,3,4-cycloheptatriene Onionization Br /.^
I i1 \_:/
Pr e
,A'.
'
(9
+Brr
t _]) + - u + Br
lndustrialArea, (Raj.) Ph.0744-2423406 Kota Indraprastha No.1, Mbrant Academy (I) Pvt. Ltd.'A-14(A)" Road
131l
12.
due (a) (i) HrCu - C - OC2H, + HBr(acid) ; (ii)no reaction to partial double bondcharacter I CH, ttl (b) (i) o2N'-,/
cHs I
Or-rzort
+ F- is liberated(ii)Bimomecular mechanism notpossible is in'(ii)case ;
cHr para is (c) (i)dueto presence lonepairof nitrogen atomNOgroup electron of denating ortho, and directing (ii)NO2 groupis electron withdrawing metadirecting and antiaromatic (d) Dueto reduction central ring,threefour membered ringsbecome of stable whileon ring of ring recuction terminal onlyoneantiaromatic canbe stabilized.
13.
(A) H2SO4
(B) Br,
Noz
lndustrialArea, (Rai.) Kota Ph.074+2423/;Cf' Vibrant Academy (I) Pvt. Ltd. %-14(A)"Road No.l,Indraprastha
a34