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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

private (India) Limited

(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

(D)I in maximum ? thetreatmentofAg@willbe

and carbocation bromide to of Ease ionization produce

(A) Y
/.-Cl

A
Br

(B)
--sggltt P ; P rvillbe

(c)

3.

\-/-.,

(c)O (B)(O2sb'6s

(D)mixture (A)and(B) of

-y

: compound is one Which of thefollowing themostbasic (C)CaHs-N(Cq)2 (B)C6H5-NHCH3 (A)C6Hs-NH2

(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:

I (A)t> ll > lll > lv

II (B)ll> lll>lv> |

i]-'oo' ,gcooH o]-*o'


III (C)ltlll>ll>lV IV (D)lit>l>ll>lv

Electrophile NO, attacksthe following:

' .'Q)',,,0J-: (")6.I-*o


@

..*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

0l) (B )lll> ll> I

OID ( c) il>lll> |
? veof Phenol

(D) t> lil > tl

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

'?c"-' (A) (A) Productis I I , "--s ? ") ^ ''. ]

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

is: inthe Themajorproductformed reaction OMe

+ (CHJ, CHCHTBT +

species : is electrophilic the of In thesulphonation benzene, active


(A) SO2 (B) SO3

(c)sol-

(D)HSO;

rate ring bromination itsaromatic at thefastest ? of undergoes compounds Which of thefollowing one (A)

is: the 21/ ',. Inthereaction majorproductformed L-/ o

J^\ \y

Br,(1 more) Fe

Br

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t4

-Y

HNo3/Hrso! Major (A) product :

MeoAA,,
(A) (B)

(c)
y

(D) MeO

Not

lncreasing orderof rateof reaction Bry'AlBr, ' with is


_a^
t'

(D
( A)i l t< t< lt< tv ,o--'/

(ID

(m)
(c ) il < t v < lil < |

(IV)

(B )lv< lt< l< t v

(D)t v < il < ill< |

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)@.-+

--0cHcr3,KoH,A+ 1sy (c)

(D)Noneof frese

Which thefolowing most of is reactive towar@ cl

Qo,r-1
t\l

O r f d*'-)

NO,

Nq

ct

\ 11 '\ \\:,/ \ ,1'.'


\Q

tl Y

1go\a16"' --) o'?''

(B) (Major), Product is (B)

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

(A)Lindane 3gy' \./

(D)Ethaneperchlonate

AIcl3 > c6HscoNH2 GuHu+A A in theabovereaction is: (A)NH2CONH2 (B)CTCONH2'

(c)cH3coNH2

(D)CH2(CDCONH2

-{

cuHui%a-h-Hees
Theendproduct theabovesequence in is: (A)Toluene (B) Ethylbenzene
.--, (9) + cHs-cH2{H24H2-cl Alcl3

(C)Bofrr above the

(D)None

-{

> hydrocarbon major productX is: (X)

(A) (c|

curcH-cH, I
CH,

cHt
(D)None iscorrect (C)Nitrobenzene
(D)chlorobenzene

n.ar}. Reaction SO, is easierin: of


(A)Benzene y (B)Toluene lf themixh.rre thefolloiving of buraomaticcompoundson oxidafonbysfongoxidising (hotKMnOo): agentgives

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

Compound Aand B respectively are: (A)o-Bromostyrene, benzoic acid (C)m-Bromosgrene, benzaldehyde

p-U (a)

benzaldehyde

,benzylacid (D)7

Thenumber benzylic of hydrogen atomsin ethylbenzene is: (A)3 (B )5 (c)2

ph.Ot4+242g4ff. Vibnnt Academy (I) h,t. L6. "A-14(A]"Road No.1, Indraprastha IndustrialArea, (Raj.) Kote

11.

F-"-s Productobtainedwhen benzoylacetic acld is heatedwith soda{me is:

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 \-:/ ,/

Ni,bishttrp' > (A).Whichofthebllouringcanbeisolatedastheproductofthisreaction. :


higbpressure

'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

*rrict rcaction f"-" on with,B,

Jcl (A)zn(Hs)+@nc. ncl, , (.,dct,NaBHo


49.

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.

Whensulphonilic (pH,NC6H4SO3H)treated acid is withexcessof bromine, product the is:

product (A)tribromo (C)monobromo product


MbrantAcademy(I)Rt

(B)dibromo product (D)tetrabromo product

L6."A-14(Af RoadNo.l,IndraprasthaIndustrlalAca,Korra(Raj.)ph.ot&2423y115 tSl

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,

were obtiained. originalcompound The is: (A)odibromobemene (C)pdibromobenzene


56.

(B)m{ibomobenzene (D)BothA& C

Which thefollowing of species expected havemaximum is to enthalpy anelectrophilic in aromatic substitution reaction?

X +E*+O '.-G )-(rD


(lll) (B)Species 57.

H-.-E&'

K*

(IV) GII) (c) species (lV)

(D)

Fortheelectrophilic nitration, reaction involving substitution whichof thefollowing regarding the sequence rateof reaction true? is t (A) kcuHot kauou kauru

(B)kcuno kaoou' kaoru '


(D) kcoHot kauoo' kaoru

= = (C) kcunu k"oou k"uru


58.

Fortheelectrophilic substitution reaction involving sulphonation, whichof thefollowing sequence regarding the rateof reaction true? is t (A) kcoHut kauou kauru

(B)kcuHu kauor' kauru '


(D) kcunu t k"uou' kaoru

= (c) kconc= k"uou 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

reactivityinelectrophi|icsubstitutionreactionsofthefollowingcompounds: the ldentifY conectorderof

(D
(A)l> ll> lll> lv (B)lv > lll > ll> l

61.

sroupq.^ir1#"llro;r##;r#R'4+'l'-No' ofelectron.withdrawine ccnjugation these is: of sroups ii"-"i",

activates

fffi"ffi:,;;H;;; mt"T;fr: o o tl
ogo null

"t"activig o

I(A) >-c=r{,> ' -n-*' J-* -No,


(B) -r'-8-n'i--on -8
(c) 4=N

>4EN'-No'

>-No2> j-H>4-R>-

? ! ^I-*
Ii
t"Q5\-*o, cHi\- ,
H'G r--'

oao

(o)-8-nt-No,

>-c=N >-e-oRt --[-*

: givencompound to prepare the Ghoose bestmethod

(D) substitution' aromatic nucreoph*ic towards mostreactive givencompound of theforowing which

n -W5, (ii)FP

--9+

. {;ff+ ' 'rsvr

ffi equivalent) (1

E(Maio0;Ecanbe:

NO, MbrantAcademyg1il-to-."a.r4(A)..Roadffi'.h'|ndustrialArea,Kotr(Rai.)Ph.o74.242y6

tr0l

Whichis the bestsynthesis of

,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.

by: can lsopropylbenzene be prepared = + (A)Benzene CH3CH CHr.'..'% + (B) Benzene


#

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

=at, 4 + (B)Benzene(CH.)2C + (D)Benzene(CH3)2 CHz c= Alcl3 )

AYct

\2

Hzo product NaoH , is:

';

(")"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
Kota Ph.074+2423/,OG IndustrialArea, (Rai.) Indraprastha N0.1, Mbrant Academy (I) Pvt. Ltd.'A-14(A)"Road 114

reaction? givesFriedelCrafts of Which thefollowing

(A) -l "v[l

.A\

X (B) I li
\2
(B)CH,=Q11 C;

reaction whenbenzene usedwithAlCla? can of Which thefollowing be usedin FriedelCrafts

(c)cH3cH2cl

(D)CH,=Q11-CH2{;

is: benzene into benzene n-propyl for method converting Thegood


+ Anhyd. + AlCl3 (A)C6H6 CHgCH2CHTCI with + Anhyd. + AlClo thentreatment ZnlHg/HCl and (B)C6Ho CH3CH2COGI + Anhyd. with + and AlCl3 thentreatment H2Ni (C)C6Ho CH3CH2COCI

cl
(D)C6H6. /\ ' Alcls

benzene? nitration slowthan will of Which thefollowing undergo

14.

group? directing isortho-para of Which thefollowing (C){H=CH{OOH (B)CCl3 (A) CF3

(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

Kota IndustriatArea, (Raj.)Ph'074,4'24234,06l Mbrant Academy (I) R t L6.'A-14(A)'Road No.l, Indraprastha

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.

Alcl3> + HCt) (acompound c10H12

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.

ring. on Substituent PhenYl (A)- CH = CH- CO2H (B) -o-S-cH3

(P)o/Pdirectors (Q)metadirectors

o tl

(c) -NH-c-cH,
(D) -s-{H3

o tl

group (R)Activating group (S)Deactivating

o
2. the Match following: ColumnI

il

(A)

(P) COrtisevolvedfromNaHCOrbythereactionof OH O'IS'A.-.NOr " t C -J

(B)

test nitroso is givenby Libbermann

(O)

>a
Noz

(C)

givesyellow oily Compounds with liquid reaction NaNO,+ HCI on

G)
H

(D)

gas a evolve colourless Compounds withactivemetals on reaction

(S)

il{c)

3.

Compounds

Substituenton pfienyl

group (P)Activating

(Q)Deactivatinggroup
H{H2

(c)

(R)o/p4irector

(S)metadirector

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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.

yourreasoning. from explain a of Outline synthesis m-nitroacetophenone benzene:

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

(c) H.c:C-ct,Atct3(1. equiv.),then Flo 1

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.

product eachof thefollowing reactions: in Writetheprincipal organic

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)

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tl5l

4.

Match column the : ColumnI

Golumnll

CI
(A)
-'\

9j

(P)Group attached benzene is a +Mgroup to ring here.

(B)

(Q)Groupattached benzene is a -M group to ring here.

(c)
CH:CH{OOH
(D) 5.

(R)Electrophile would attack ortho paraposition. on or

9J
x

(S) Rateof electrophilic substitution lessthanthat is of benzene.

Match column the :

ocH

NO,

NO,

X= halogen ( A) . F ( B) - C l

(SNAr). relative reactivigtoward

(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

Izct (D) lO l+Kl---+?


\./

(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,

(D)r, andrrare notcomParable

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.

(A)major. istrisubstituted of The benzene. structure A is : A

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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

Which thefollowing of compound notformed. is

1i1ay'FeBr.
X represents mixture organic of compounds. mixture The doesnotcontain.

(D)allofthem

Mbrant Academy (I) Pvt. Ltd. "A-14(A)" RoadNo.l, Indraprastha IndustrialArea, (Raj.)Ph.O7M'2423406 Kota

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

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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

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I
I

(A)t>lt >lll>lv

(B )tv>ilt>il>t

(c )lt > |> ill> t v

(D)il> ilt > t > t v

pEE2003l

(A)ozN@tt,

,r,t")*@"r, \-/
HzC/

,.,::;)*_@*o,
NH2

H:c... -lr{g}uoe ,o, "r.

of is: Majorproduct abovereaction

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

cH3 (cicH3Osolfru +cH3cooH (D)

Oto2o,

product'X' thestructure themajor is of

'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

(S) Esterification acetic anhydride with

CD Dehydrogenation

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[231

21. Inthereactior r..$d

(1) NaOH/tsr,

.NH,

T the structure the product is. of T

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,

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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

ilaoH(aqHBr2 intermediate(s) ) the is(are)

pEE2010l

o
Br
(A)

(c)
Br Br
Column-ll

Matchthe Golumn n. Column{

[rT20r0l

(P)
OH OH

Racemicmixture

ll (B) H3c*-9-cH,
tl cH3 cH3

(O) Addition reaction

(R) Substitutionreaction

tol.t+cr

Baee)O

(S) Coupling reaction (D Carbocationintermediate

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l20l

EXERCTSE rV(B) t.
2, 3.

acr, +(cH.)rcH.cH2cl >(n)


(i)Br".Heat.Lieht

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< \:,/

czH,oH(aq) sorution , acidic


H3 cH.
[261

crnros(uq') , neutral

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(b)

,,,

NaoH(aq') (tiberated) t F
I

orrV cHr

n/F
ill liiyup\
cH2NO2

NaoH(aq')F is notliberated ,

s1)
Noz (cl

,()

Noz

(d)

is formed not but

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

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azn

r. c
8,4 15, A 22. C A.B 36. B
l|3.0

2 .8 9 .D 16. D 23. A 30. B 37. C 4 .4 51. A 58. A 65. A

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

6.C 13. B 20. B 27. D

7.8 14. B 21. D 28. A 35. D 42. A 49. A 56. A 63. B

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)

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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

A-+P;B-+Q;C+R;D-+S 88.C9.410.A D15.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

2 0 .( A) - +R Q,T; ( B) - +P ,S ,T; (c) -+ R, S ; (D)+ P 24. A,C 25 . A,C 26. AC 27.

A -R, S ; B -T ; C-P , Q , ; D-R

F,(ERCISE IV(B) CHTCHT CHBCHT Br^

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'

, C5HrCHGgg ""1 OH;

C.H.CH=CHCHOffi#C.H'CH=C=CH OH
Soda lime

. ott-

C.H'CH=C=CH

(b)

6.

c6HscH2cH2cHctc6H5 -q-t

c.HucH= cHcoHs (Cis trans forms) and


l30l

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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

, N aoH ,[rrt -.,

O).Ia

Me2Soo V,

.4..' lCl

OMe

OMe

c o n c . H, S o o n-\-] fO so3H

Na o H, /

rout Alternative Br -'^'Br -\ M%so;-pffi# OMe

I ONa
OMe OMe

-A..

lCl
ONa COOF{ 9.
,\

HrorIo l *-A..

{2

OH COOH COOH
tlBIi/KHF?

lgj -T-'LQ-[*o.* ---conc.llrsor -\

OH C=CH{FIO

10.

tol
\-r^Cl

(B) Enol conjugation is due Enolform morestable to extended

o tl

c-oH

(A) Moo > -fr to'l


11.

\.^cr

gives tropolium whichis aromatic 6r electrons. ion with 7-bromo-1,3,4-cycloheptatriene Onionization Br /.^

I i1 \_:/
Pr e
,A'.

'

(9

+Brr

givehighly with cation unstable antiaromatic as can'tionise itwillinthatcase 5-bromo-1,3-cyclopentadiene 4 r electrons.


t

t _]) + - u + Br
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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

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a34