Hydrocarbons

NCERT Topicwise Analysis of Previous Years' Last Three Years' Weightage

NEET Questions
No. of Questions
NCERTTopic 6
2021 2022 2023 f-
- -;; 5
9_2 Alkan_e_s - - - - - - - - - - - - - - - t - C
0
1 ·. : 4
9.3 Alkenes "'QI
_ Aromatic Hydrocarbons
95
53
0
0 2
z

0
2021 2022 2023

l!J Introduction
► Organic compounds composed of only C and H are called hydrocarbons.
► The main sources of hydrocarbons are natural gas, petroleum and coal.

DI Classification
► Depending upon the types of carbon-carbon bonds present, hydrocarbons can be classified into three main
categories :
(i) saturated (ii) unsaturated (iii) aromatic.
► Saturated hydrocarbons contain carbon-carbon and carbon-hydrogen single bonds. If different carbon atoms are
joined together to form open chain of carbon atoms with single bonds, they are termed as alkanes. On the other
hand, if carbon atoms form a closed chain or a ring, they are termed as cycloalkanes. Unsaturated hydrocarbons
contain carbon-carbon multiple bonds (double bonds or triple bonds or both). Aromatic hydrocarbons are a
special type of cyclic compounds.

EIAlkanes
► Alkanes are saturated hydrocarbons with general formula CnHin+i• where, n is equal to 1, 2, 3 .... e.g., CHimethane),
C2H 6 (ethane), C3 H 8 (propane), etc.
Structure
► Each carbon atom of alkanes is in sp 3 state of hybridisation with its four bonding orbitals directed towards the
four corners of a regular tetrahedron. All the C - C and C - H bonds are strong sigma (cr) bonds. Every C - C
and C - H bond has a length of 1.54 A and 1.09 A respectively. All bond angles are of 109°28'.
Isomerism
►
Alkanes exhibit chain isomerism.
 ~tG- Objective NCERT at Your F·
188 . . . . inge~i
, etlvrnca ) lo not exh1b1t 1somensm, the nurnbe ~
► Although thr first three mcm l)Crs (niell,anc, · ' ' nd propane c
. · . ·b 1 atoms. Thus, butane has two iso r.of is°Iner
. I I .
in other alkanes 1ncreaSl'S w11 't 1e rncreaS(, .11 i thc number o. 1ca r or and ' 111
, l . , octnnc 11 1 clccane as many as seventy five1e s,. Penta~ I
has three, hexa ne has ltvc, hcpt ,inc 135 nine, has erg l ee r , isorn e
' · <;::H ers.
CII I I J

c:t i,-
I
c: 1i - c11 i - r. 1-11' l ',H ' - C-
I CH
C:,111 2: l'H, - t' ll~- l' ll ,- C'II J- CII,, 3
II 1'•' 111 ,1111' / , ,, 1'1'111 ,llll' CH l
//1.'0 •pcnt one

Prepa ration
, . . lro .
► By hydro~cnntion of unsaturntcd hydroca rbons. 1)1 1iyc gcri g,as IIadds to '[l1is alkcnes and alkyn es 111 th e pre)
process is ca ll ed h d encerif
ti1wh· \livi ,kd l",1t.1lys1s likeph1t1.1H1rn,pa 11 .J(.tlltnO
1. . ·ck. ~! to form a canes.
I 111 c y rogen .
atio0
l't/Pd/NI CH
., • C ll ::: C l-1 +2 11 2 --- ➔ CH3
1·1 r.1 N, C (' I I . -
t.:11 : = C\\ 2 , 11 ~- -~ ll.1 - ·J
l 1h,•1w I 1h,11w Eth;inc:
lith )' 111 •
► Re-duction of alkyl halides: Alkyl halides (cxccp l flu orides) on reduction wi th zinc and dilute
hydrochloric acid
~iw ,,lk.mcs.
1' - \ + H , /J\IICl R- H + H X
> Wurtz. ~action : Al\...·y l h;1lides on treatment with sodium metal in dry etherea
l (free fro~ moiSt ure) solutio;i
gi,·e higher a.lbnes. This reaction is known as Wurtz reaction and is used
for the preparation of higher alkan~
cont.1ining even number of carbon atoms.
JI RX - 2;-..:.:i ... :\'.R ~ R - R + 2NaX
L'tht' r

► From carboxylic acids :

► Decarboxylation : Sodium salts of carboxylic acids on heating with soda lime (mixture
of sodium hydroxicc
and calcium oxide) give alkanes containing one carbon atom less than the carboxy
lic acid. This process c:
elimination of carbon dioxide from a carboxylic acid is known as decarboxylation
.
RCOO~ a ... NaOH Cao, 630 K > R- H + Na 2C0
3
► Kolbe's electrolysis : An aqueous solution of sodium or potassium salt of a carboxy I
lic acid on electrolysii I
gives alkane containing even number of carbon atoms.
Electrolysis
2RCOON a + 2Hp ---'---+ R - R + 2C02 + 2Na0H + H
I 2

r At anode:
0 0
II _ J . 11 •
2R-C- O ~ 2R-C- ~: ~ 2R + 2C02t; R+ R~ R-R
Acetate ion Acetate free radical Alkyl free
At cathode : radical

Hp+ e·~o w+ H;2H ~HJ i

Methane cannot be prepared by this ~ethod.
Physic al Properties
> Due to presence of weak van der Waals' forces the fi t f
C18 and above are solids at 298 K. "d'
' irs our members, C1 to C4 are gases, C to Cli ,ire Jiqui ~
5
► All alkanes are colourle ss and odourle ss insolub l ·
► The boiling points of alkanes increase with' increasee. m water
l
but dissol . l I
ve m non-po ar so vents.
decreases with branching. 1·111
' 111 mo ecular
' ma d t·
'ss an or the same alkane the b01ln(J po
t o
► Alkanes with even number of carbon atoms have higher melt· .
alkanes with odd number of carbon atoms d t , higher
' mg pomts than the next lower and ne:d
ue o symmetry.
Chemical Prope rties
► Alkanes are generally inert towards acids bases ox·d· .
following reactions under certain condition~. dergo
, I ismg and reducin g agents. However, they un
Chemistry Hydrocarbons
J
189

~ Halogenation: CH 4 + Cl2 520

!'~70 K
C H 1Cl 520 -hv6701\,. CH 2Cl2 s20 -h6701,
.
v
,~ CHCI 3 hv
520 670 K
CC I
-1

nes with halo ge ns is F > Cl > Bi· IJ•

,. The rate o f reac tion of .-ilka 2 2 2 >
ogen s of alka nes is 3° > 2° > 1°_ -
► Rate of repla cem ent of hydr
. re.-ic t"
•I .-incI a reve rsibl b - .· .,
► Fluo.rina tion. is, too viole nt to be controll.ed. .fod. in nti on is, very sow e It
,on. ca n e can 1eu
h . , . . ts ltkc HI OJ or HNO ,
out mt e pr e~ence ot ox1d1s111g agen 1

CH-1 + 12 ~ CH.1 1 + HJ ; HfO 1 +SH I ➔ 31, + JH JO .

· - -
,. Mechanism :
Chain initiation step : Cl - Cl ~ 2CI
Chain propagation step :
CH~ + c I--~ CH _ , + 1-1 -- c I ; c 1-1_·1+ c 1- c 1- - . c I-11c· 1+ c· 1 ..... :.in d so on
step :
. in. terminating . .
Cha
Cl+ Cl ~ Cl 2 ; CH., + C l -➔ CH.1C l; CI~13 + Cl~I 3 - - - ) CJ-1 1 - CJ-1 3
• Ease of substitution of various hydroge ns fo ll ows the sequen ce
3° > 2° > 1° and th eir . rates vary
- re1at1ve

+ •
·th th
,-v-1
-
e natu re ot halo gen,
The relative rate of substitution of 3°, 2°
and I hydroge ns with Cl2 at 298 K is 5
O : 3.8 : 1 whil e with

Br2, it is 1600 : 82 : 1 at 400 K.

► Combustion :
311 +
► Complete combustion : C,,H 2,, + 2 + ( 2
1) o2 ~ nC0 2 + (n + 1)H 2o
Incomplete combustion : CH 4 + o2 ~
C + 2H 20
►
limite d Carbon
black
► Controlled oxidation :
2CH..' + 0 2 Cu tube 2CH 30H ; CH 4 + 0 2 Mop 3 > HCH 0 + H?0
3 Me thano l ~ Metha nal -
(9 · 1) 100 atm/SZ K

(CH 3COO ), Mn
2CH3CH 3 + 302 - 2CH 3C00 H + 2Hp
~
Ethan oic acid
KMn 04 s)
(CH3 bCH (CH 3b C0H (For alkanes having 3° H atom
oxida tion
2-Me thylpr opane 2-Met hylpro pan-2 -ol
CH~
I "
. n: C H (CH )iCH Anhy. AIC1 3 /HCI
. aho
> Isom eris > CH 3-CH -CH3

> Aromatisation ·CH

3

6 14
2 3

• L
11-Bu tane

. exane
11- , 1
Crp 3 or Vz05 orMo p3/Alz03
773 K/10-20 atm )
o~ I
iso- Butan e

+ 4H2
Benze ne

> Reaction with stea m : CH 4 + H 20 + CO + 3H 2

C6H1 2 + H2

C4Hs + C2H6
► Pyrolysis or cracking : C 6 H 14
C3H 6 + C2H 4 + CH4
Conformations groups about C - C bond axis are
> The different arra ngem ent of atoms
in space that results from free rotation of
n as conformational or
d conf orm atio nal isom ers or rota tion al isomers and this phen ome non is know
calle
rotational isom eris m. ,,.,---.r;:r,i1
► Conformations of ethane : ~ arra ngem ent of hydrogen atoms) are poss
ible for ethane, if
conf orm ation s (rela tive
► An infin ite num ber of
cule undisturbed.
g the C - C axis keeping the rest of mole
one of the methyl grou ps is rotated alon
is by an angle such that
In this conf ormation, rotation abou t C - C single bond
► Ecli psed conf orm atio n :
s of rear carbon atom
pletely cover or eclip se the hydrogen atom
hydrogen atoms of front carb on atom com unstable.
on are visible. This conformation is most
i.e., only three hydrogen atoms of front carb
 wt,t G- Objective NCERT at Your F'
. l b d . b inge~ip1
190 . b t c-C smg e on 1s y an
• · 1at1on a ou h angl
• onforma11on, 10 ' . e from each ot er making it es
► Staggered conformation : In t 111 s c . . , al maximum di st anc stable b0
.. ·bon atoms ,He . '
that hydrogen atoms of. two L.lt
1/

12 s kJ/mol as compared to eclipsed conformation. . . cdiate conformations between the two e

-- '. . . I . f 1ossiblc 1nte1 111 ' . Xtren
► Skew conformation: The inltn1te num )Cl o I _·.', I t .1s skew confornrnt1ons. 1e
. . d . , -,d) nn.' refctr ec O • · 1-1
conformat,ons (eclrpsed an staggerc H

7
1-;H· ·l l ) H .. II 11 _. . 11 /&·I H~l-1 H~l
II H H
H I\ I I. ::: H H 1-1 I-I H ~\ H

H
>·-1-1 11
/ '• II 11 / ·II
lidip~cd Staggered
II
Skew
C,Htdw,,r !'- 1',' W f,,nn
Fulh ,,·lip., ,,t r.,nn ~1.1~,:,' "'' 1,,rn1 New man projection of ethane
s.,wlwr~l' l'l\'k<li,,n ,, .. l'lh :llll'

D) Alkenes
►
. h;1ve gene,.a I for.mu la' C 11 H 211 are called alkenes. They contain dou ble
Those uns.1tur,l!eJ hydrocarbons whteh
~ which is consrdaed
bond (C~ == C) . · ·
as ;1 lunctwna .
I g1oup, e·g., C 2 H ,, (ethene or ethylene), C3 H 6 (prop eneor
rropylene ).

Structu re
► In ethylene mokculc', one' of the' sp 2-hybridised orbitals of one carbon atom overlaps axially with one of the sp2.
orbitals of mother carbon atom. Two of the sp2-hybridised orbitals of each carbon atom overlap separately and
along the' a.'\c'S with the' ls orbitals of the hydrogen atoms. The pure p-orbital on each of the two carbon atoms
0\-erlap c'ach other latc'rally (sideways) and thus, a new type of bond (rr) is formed between the two carbon atoms.

Isomerism
CH 3
► Chain isomerism : This type of isomerism is shown by all I
. 1our
alkc'n es h avrng c or more car bon atoms, e.g., pentene H3C- CH2- CH2- CH= CH 2 ·, CH == C- CH CH
2 1 3
has following two chain isomers. I- Pentene 2-Methyl-1-butene
► Position isomerism : The two isomers differ in the position of double bond kno
,
·t· ·
wn as posi 10n isomers. e.g.,
CH 1 =CH-CH 2 -CH 3 ; CH 3 -CH=CH-CH
I -Bu1c:ne 2-Butene 3

► Ring chain isomerism : In this type of iso · · ·

chain, e.g., mensm, one isomer is open-chain compound and the other is closed

fH2-,H 2
CH2-CH2
Cyclobutane
► Geometrical isomerism: A carbon-carbon double bond . d
of rr-bond prevents free rotation about the d bl b is ~a e up of one cr-bond and one rr-bond. The presence
djfc ou e ond with th I f ·
e resu t o the type abC = Cab can exist in n,,o
ierent geometrical isomeric forms i e . c
. , . ., c1s-1orm and trans-for
► ~he isomer in which two identical groups lie on th m.
side of the double bond is called . . e same H3C, - /CH3 H /Cl-l.1
. c1s-1somer and th h ,
isomer in which identical groups lie on the o . e. ot er H / C- C "-H '\.. c== C,c1
the doubl b d · U ppos1te sides of H c/ fl
e on is ca ed trans-isomer. cis-But-2-ene 3 B t ?-en~
trans- u --
► Thus, cis and trans isomers have th
► Ge ll . e same structure but ha d 'fC
nera y, trans-isomer is more stable than th . . ve i ierent configuration.
e C1s-1somer because fl
Preparation esser crowding in trans-isomer. °
► Partial hydrogenation of alkynes :
► Hydrogenation with Lindlar's catal . .
yst . Partially deactivated . , J st.
pallad1sed charcoal is known as Lindlar's cata y
chemistry I Hydrocarbons
191
R R
R- C =C - R + HJ
Alkyne
Pd/C
- (Li ndl ar's ca lnl yst)
'c-c,,,,
/ - 'H
I-I
cis-J\ lkcnc
► Birch reduction :
=C-R Na/Liq. NH3 R'- / H
R- C - > /C=C'-
Alkyne H R
1,·1111; -i\ lke ne
► By dehydrohalogenation of alkyl halides :
► This is example of ~-elimination reaction, since hydrogen atom is eli minated from the B-ca rbon atom
(carbon atom next to the carbon to which halogen is attached).
l~_ Cla_ ale. KOH
-C
I I
----)C=C(
t,,,
+H X
H X
► Nature ~f ~a.lo_g en atom ~nd the alk~l grou~ determine rate of the reaction. It is observed that for halogens,
the rate is: 1odme > bromme > chlorine, while for alkyl groups it is : tertiary > secondary > primary.
> From vicinal dihalides :
CH 2Br-CH 2Br+ Zn~CH:!=CH 2 + ZnBr 2
CH 3CHBr-CH 2Br +Zn~ CH 3CH=CH 2 + ZnBr 2
► By dehydration of alcohols :
The alcohols on heating with cone. H 2S0 4 form alkenes with elimination of one molecule of water.
I
-C-C-
I 95% H?S04
-
'c-c/
,,,, - ,
I I t,,,
HOH
Saytzeff rule : If a single starting compound can yield two or more isomers then more substituted alkene is
formed in greater amount.
IDffiP/JJ$
• During dehydration of alcohols, sometimes unexpected or rearranged alkenes are formed due to 1, 2-hydride
or 1, 2-methyl shift to form more stable carbocation.

Physical Properties
► The first three members are gases, the next fourteen are liquids and the higher ones are solids.
► All alkenes are colourless and odourless except ethene which has faint sweet smell.
► All alkenes are insoluble in water but fairly soluble in non-polar solvents.
► Boiling points of alkenes increase regularly with increase in size and straight chain alkenes have higher boiling
points than isomeric branched chain compounds.

Chemical Properties
R R R R
I I . I I
R-C-C-R .
XifCCliether cold, alk. I<Mn04
~

Halogen ation Baeyer's reagent

R-C-C-R
I I I I
X X OH OH
cis-1, 2-diol
R R
I I R R R R
• HzfPt, Pd, Ni
R-C-C-R "c = c/ . I I
I I
H H
Hydrogenation
14-- /
R R
L--.....1,
"H-X
H ydrohalogenation
R-C-C-R
I I
ALKENES H X
R R
I I HP/H2S04
R
R-C-C-R (i) 0 3 (ozonolysis) .,
~
~

Hydra hon - 2 "c= o

I I (u)Zn+Hp I
H OH R
> Markovnikov's and Anti-Markovnikov's rule:
Markovnikov's rule states that negative part of addendum (adding molecule) gets attached to that carbon atom
which possesses lesser number of hydrogen atoms.
 ,AA;t;G- Objective NCERT at Your F
nv ingeh
'llj\
place contrar y to Marko
Jkenes takes vn1kov•1
rnrn e trical a
f HBr to uns Y t
roxide, addition o [(harasch eff« . - C!-1,
192
In the presence of pe eroxide effect or ~ R - ClJ-I
ru le. T h.JS JS · known as P 1-1-Br R _CH=== CI-I B
2
B ◄ Alkcne r HI,s a dditi on)
Markovn1'kov
CH 2- r Pcrox1'd c
R-CI-I? - (
HCI and .
. M ko-vnikov's addition)
(Ant·1- 'dar or Kha rnsch effect) I not with 2n + 2 - n2 h
O
fHBron y, . I 2 w ere,n," nu~ber
<"=" . obse rved in case
Peroxide effect is . h drocarb on is • given by·

t'on ma y toms.
+ • The number of degree
of unsatura J
n - num
of carbon atoms, 2. -
ber of
double
hydrogen a
bonds are
known
Dienes
as dienes.

. . Alkenes with two ~I

• Dienes•
i ., frOill
,vidO~
~ Conjugated
cumula ted
dienes
Isolated dienes
dienes C
I _ _ c==C-C== - - C=C=
I
C-
I
physical Pro
-C=C- C-C-C - I I I I
I I I I I first three I
High temp./pres sure + CH-CH z Ti .,., All a11cynes
► .r 3- CH= CHz)
. • : 11 (CLJ
Polymerisation Catalyst I
cH AllaU<ynes
►
~w~~
3
. ., Melting po

h d to the doubly hon d e d carbon atoms, moreasstable 1s the alkene. Chem ical Pt
+ .• Greater the number of alkyl groups attac e
Add
·r
t
of symmetrical. .reagen s ov roduct;
t . I alkenes can be genera lised
er symme nca lkene + syn
. .
:
addition ➔
.
racemzc pro d
d t
uc Acidic nature :
➔
_ trans-a . .
1 10n

. alk anti addition

➔
meso p. pro duct·, - trans-a lken e + anti add1tlo n
+ syn addition ➔ racemzc
- cz·s-alkenee +
mesa pro uct.
Ac
c1s- en • f ddition .
CHan I a
e.g., Addition of halogens to alkene is an Tb
. CH 3 3
is .
4
H+B r Br+ H H <CH CC1
Br-!'.-H
Br+H
H H cc Br; CH )c= C H 3 + Br
'c=C:::CH3
CH{ + Br, - Br H+H
2
--....,,
4

► Addition 1
CH3 3
trans-2-bu tene
cis-2-butene CH3
(Racemic mixture)
(±) 2,3-Dibromobutane
CH3
meso-2,3-Dibromobutane
CH== cH~
III Alkynes
► Those unsaturated hydrocarbons which have molecul ar formula C,H 2,_ are
called alkynes. "
CH:::::cH ~
► They contain
(or methyl triple e).
acetylen
~ 2
bond, e.g., C,H, (HC CH) called acetylene or ethyne and HC as CCH
called propf
3 ► t·tnear po:
atom which is moll
more acidic than alkenes and alkanes because .they have sp-hyb ridised carbon
They areegative.
> electron
),.
Isome rism
Cyclic Pol
► Ethyne does not show any type of isomerism.
► Other alkynes can form chain, position and function al isome - ~ron
rn,-rn ,-rn,- c==c -H , rn,-CH,-c= .
=c-CHrs. ),.

1-Pentyne 2-Pentyne 3, ► Aromatic

(B)
(A)
A.renes ca
CH,-yH-c "=C- H CH,-cH cec CH-cH cec CH,
~.
less th .
an '~
CH3 l.3-Pentadiene
(D)
· ~ ()
3-Methyl-1 -butyne
(C) ),. tn~"c la
A and B are position isomers; A and C are ch . . 1'he ar

CH3-C
-
=CH and -
Q are ring-cJ1
a1n isomers; A and D
• .
am isomers ·
are
.
functio nal isomer s.
... 0 111
Nttc1,
Propyne Cycloprop cne
<tflcl SJ
►
che111is1ry I l-lydrocarbons 193

structure
► In ncc t~lc nc mo lc_c ule, o ne of thL· sp-hybr ld isc d orh llul~ <)f o:1c 1.:i rh o n :110 111 ovnhps axially wi lh on l' of !h e
. hy brid ised orbit a ls of tlw n thn cn rh o11 .i trnn : lhu s a< .
.\ 11-
(, rr bo nd is• lormcd . s .. . i rid ·' /I I1y I)r ·t1l ·l 'i (.' ( I or I) ·I 1a I
, ,. C(

o m ove rlaps, axl ull y and se parate ly• wl l h 1lw I s nr hi111 ls' o l I lw I wo hyll I.<> g c 11 ;110111 i-. anc.I l Il ll ~ l WO
Of eac h cn rhon at • , , •
C - H cr-b? nd s arc l~wnH:d_. I he re111 n111 i11 g lwo 1 11 r,· /' orli ilals
1 o l <lll c L:t rh o 11 alon, ove rbp . , 1- ickway i> wi lh th e
correspo nchng p -nrb,t als ul th e ollw r ca rb o n 1110111 11 11d tl111 s, lwo ( ; C n bond s arc lorin cd.

preparation
> from calcium rnrhidc: CaC0 _1 ~ CnO + CO 2
CnO + JC ~ CaC 2 + CO: CaC 2 + 2Hit) - >Ca(O l 1) 2 + C LI 17.
Cnlci um cnrhidl·
II 11 11
f rom ,,icinaJ dihalides: H 2C-t - H + KO H -; ~~.:~
I I
•h;• d
r -11 ;
1
~~ = / NaN I
12
- Na llr/ - N I 1 1
~ CH = CH
> · \

Br Br H Br
Physical Properties
> First three members are gases, the next eight are liquids and th e hi gher ones arc solids.
> All alkynes are colourless and odourless except ethyn e whi ch has characteristic odour.
> All alkynes are insoluble in water but soluble in non-polar solvents.
> Melting points, boiling points and density increase with increase in molar mass.

Chemical Properties
Na + - _ 1 j
Acidic nature: CH=CH - - - - NaC=CH+ 2 H2
Liq. NH 3

Acidic character of hydrocarbons decreases in the order: CH=CH > CH 2 CH 2 > CH 3 - CH 3 =

The group -c-cH (1-alkyne) is acidic in nature due to mores-charac ter (50%) of C = C which
is sp-hybridised. Hence, proton release in -C=CH takes place more readily.

· · • Ni H 2 CH2 H CH3
> Addition reachons : CH= CH ' ) 11 --4 I
523-573 K CHz CH 3

CH= CH Cl2/CCl4) trHCI Cl2/CCl4 ) f HCl2 CH - CH HBr) trH2 HBr) fH3

CHCI CHCl 2 CHBr CHBr2

CH -CH HzO. H2so 4 ) fiH2 Tau to rn erises ) CH CHO

3
HgSO4 , 333 K CHOH
► Linear polymerisatio n: nCH-CH ~ fCH=CH-CH =CH+n

► .
C 11c . . _
ye polymerisaho n : 3HC = CH
red hot Fe tube
873 K
> 0
Polyacetylene o r polye th yne

::::,-...,_
I

le Aromatic Hydrocarbons
► Aromatic hydrocarbon s are now called arenes. Benzene is the simplest aromatic hydrocarbon.
► Arenes can be described by the general formula C,,H 211 _6 m, where, n is the number of carbon atoms and r, is not
less than six and m is the number of benzene rings.
Nomenclature
► The aromatic compounds has two main parts:

and single bond. It is represented •o

► Nucleus: It is benzene ring where all the six carbon atoms are in sp2 hybridised state as there is alternate double
or

O
or @
 Wvt G- Objective NCERT at I
194 Your Fin
zene nucleus is called side chain. Tu· . 9e~ip1'
. . • p attache d to ben is is 06
lain
1> Side chain : Alkyl or any other aliphatic grou . b !kyl groups.

V
1
th
by replacing one or more hydrogen atoms in e nng y a f • is ~I
en atom O nng
h d O
► Monosubstituted derivatives : If one of th e Y r g

a~
bstituted
. h I·t . ailed as monosu .,,, {
su bstituted by an alkyl radical or a group t en is c I

0 U A9
. . 0\
d envat1ve.
► Disubstituted derivatives : The position of second sub ituent
st A A A

with respect to first one will form different forms. For example,
1 6 "" I2 A A
2nd and 6th positions of a ring with respect to first are called
6
1/ I
2
5 ~ 3 ~ I
3
ortho-positions. 3rd and 5th positions of a ring with respect to 5 ' 4
h h t to 4 (1, 2-)ortho (1, 3-) meta A
first are called meta-positions and 41 position wit respec
first is called para-position.
If side chain contains a functional group, then these are said to
@r yI-I--clil 11
(!, 4-) Para

be phenyl derivatives of the corresponding aliphatic compounds. OI-I

1-PhenylethanoJ
Isomerism
► All six hydrogen atoms in benzene are equivalent hence, only one mono-subS t ituted derivative is possible.
► Position isomerism :
► When two substituents are present (either same or different), three position isomers are possible.

~
$$
p-isomers or 1,4-position
a-isomers or 1, 2-position m-isomers or 1, 3-position

► When three substituents present are identical, only three position isomers are possible.
X X X

I
@r; ~yx
X
xkx
► When two substituents are same and one is different, six isomers are possible and if all three groups are
different, ten isomers are possible.
► Functional isomerism : This can be seen in phenyl alcohols and phenols, e.g.,
CHpH OH

Molecular formula = C7H80 : ~o

LS) ~o cH3
LS)
Benzyl alcohol o-Cresol
In the two compounds the properties of the -OH group are different.
► 'fautomerism : Keto-enol isomerism is also found to exist in acetophenone due to the presence of mobile
a-hydrogen atoms, e.g.,
0 OH
II I
(r\'(C-CH 3 (r\'(C=CH
~ ~~ 2
keto-form enol-form

Structure of Benzene
.n
3110
► In benzene, each carbon is sp -hybridised. Two of the hybrid orbitals on each carbon are used for the forJ11
2
(
2
of cr-bonds with two adjacent carbon atoms whereas the third sp -hybrid orbital overlaps with the a-orbil~~;s
H-atom to form a cr-bond. All these lie in the same plane. The unhybridised orbital of each c -atorn over
equally with unhybridized p-orbital of both the adjacent C-atoms to which it is bonded.
 chernistry I Hydrocarbons 195
e to reso n,1 n ct: .
It has high degree o f unsatu ra ti o n and hns unusua l stnl:iili1 y du
~

Huckel Rule of Arom aticit y

t lw r li .,v1• h t ' ll t L'lll' 1 in~; .ind JH J,, L'~ , th L'
\ > Huckel rule of nron~at_icit y is applil'd tn nll th e ri ng S )'S lt:111 ~ whl' 0 1 11 0 1

fo llow ing char:1c tcns t1 cs :

► Planarit·y
,. Ccimpk te dt'1lK,llis4'tion l,f rr -ckctrn ns in thl' ri ng
(
,. Prese nce of (-111 + 2)rr -dcl°ln ,ns in the ring. wh ere II is un l nkgcr 11 0, I , 2, .. ,)
For exa mrk,
~ fl
0 0 0
Cv,l,>hq ,1.11n,,ny l
,-.111,,n __/
co N,,J'hlh.l l,•,w
(11 • :!, 10 n l'i<'clron , )
~
V v·~ cr f
'------ - - - - ·'-"'-'~
(11 • l , c- n ,•k ,:-truns) ------
(11 • 1, I~ n l'l •·<lron,)

Aroma tic Anti-aromatic Non -aroma tic

• Cyclic, planar molecu le • Either non -c yclic or n o n -
, c ,·dic , pbn ar molecu le
planar
n of • No del ocalis atio n of rr
• Co mpl ete deloc alisa tion of n: • Compl ete deloca lisatio
n:-elec trons electro ns .
d e'C trons
• May or ma y not follo w
• Follow Huckel 's rule (4n + 2) n:e-s • Follow 4n 1te-s
Hucke l's rule.
• e.g., cyclop entadie nyl cation, • e.g., cycloo ctatetr aene
• r:.g. , cycloh eptatri enyl cation
cyclop ropeny l anion, etc. (tub-sh aped), etc.
(tropyiiurn ion), cyclop ropeny l 1

ca tio n, benzen e, etc.

Cyclooc tatetrae.ne
Cyc lopentadienyl cation Cyclopropenyl anion
(No n -aromati c)
(Anti-aromatic) (Anti-aro matic)
Cyclopr openyl
____ cation (Aroma tic) _ _ _

Preparation of Benz ene

► Cyclic polymerisation of ethyne : 3CH = CH red hot Fe-tube )

873 K
@
COON a

> Decarboxylation of aroma tic acids : @+NaOH

OH

' Reduction of pheno l : @+ Zn ~ @ +ZnO

Physical Properties
> Aroma tic hydroc arbons are non-p olar molecules.
> These are colourless liquids or solids with a characteristi
c aroma.
> These are immis cible with water but miscible with organ
ic solvents and burn with sooty flame.
196
increases
with increase
in the molecular size
_
.
M ,tG - Objective NCERT at 1'10 ur Fin
du e to inc rea se m van

m- and p-xylenes, the p-isome

.
der 'w 1 , ,·
aa s fGte,__
r has the h·
qE~.

'gh~
-1
I
► Bo ilin g po int of arenes d sm11 metry. A.II1ong
0 ' 1
. ' .. - --
of attraction. lecular s12e an
d
Melting po int depen s on
mo
►
melting point.

Chem ical Properties en es

an d alkynes be ca us e th
ut the be nz en e rin
eir n- ~l ec tro ns are involve
g is ele ctr on_r:1ch so ~e
d_
e_lec tro ph_iJe in
A~
(ILle
stlOIJ'IS
fs glvf
less reacti~e than a~ o2n
op hil ic su bs tit ution reacti •i:i. Atable
► Aromatic h drocarbons are for addition reacu?nhs. ~o ca rb on s undergo electr f s f co1111e
le
delocalisati:n and not availab · Thus arornauc diY . an d ox ida tio n reac ion ·

►
replace H-atom of the benzen
Under special conditions,
e nng.
the
I undergo ad no n
y can a so
@ tJCfR
- etas~
Oxida tion _ Add ition wh ic h •
~ ,_'\tro_philk substitution ---- .: 1. hydroc a
- Eiec
,\

a ,,
conc. HN O3' 15(2 0 2 JC!:, UV,
(a) Sa t!
r
602, cone. HzSC).i, 500 K I

anhyd . Al 0 3 anhyd .
heat ,
RC0CI/ RO,
Al 0 3
323-33 3 K
~, (b) Un
(RCO)zO , anh yd. dark, cold '
HzS 04 AICl 3
1,
CI (c) Ar ,
,,anh yd. AICl3 ,, 1
1

'
~ so ,H COR
0
c1Yc3YC1
@
Cl

~ 2
6C 02 +3 H 20 O o
(Co mb ust ion )
CI
0 (d) All

Alkc
(S" lph ~a, oo) @ afts
(Friedel-Crafts
alky lation)
Cl~Cl
Cl (Ni trat ion)
Cl
Cl
Cl .
2. The RH
(a) m 1
(Friedel-Cr (Ha log en a tion )
e
Su bstit ut ed Be nz en
acy lalion)
l Gr ou p in M on o - (c) bl
a Functiona
Directive Influence of ric effect ( +M ) inc rea se
s ele ctron densi~'at
sitive mesome 3. W hic h
dir ect ing gr ou ps : Groups with po
► Ortho and pa ra
. (a) S<
tions due to delocalisation
o- and p-posi a1

&-~-\)
rJ
6
(b}
(c) 11
(d ) ~
OC H -0 -
(Here, X may be -C H3 ,-C 2H s, -O CH 3,
on o- andp-posit
-N H 2, -N HR , -N HC
ion s becau th l 3,
se . ese are e ec tro n nc
H, F, -C l, -B r, -1 .)
· h po sit• • ns .
4. Thej
Thus, electrophile attacks t·
io d
an C, ff ,
ou ps : Grou ps with neg me nc eff, t ( M) d s ele ctr on de n sity on o-
> Meta directing gr a Ive me so
. n. ec - ec rea se (a) :
. . , so electrophile will attack on n1-pos1. tio

V' o
:
p-positions

6-6-~ _~
s.
An ii
(a)

~ ~ I ✓-:
(b)
CO +
HO
(Here, X may be -N O -C R, -C OO H , -C 00 R ,-s
o H
k)
' 2, - 3 , -C N)
.L \ irecting but dea ti .
.
~ • Halogens are o, p-d c vatrng tn na tur e. (d)
6,
ID Carci nogeni ci ty and t ox,c. .,ty . . d
\vllj
(a)
hydrocarbons
► B~nzene and polynuclear ining mo re tha n t~.. b • aJJ Cb)
ducing (c . conta •Y O en .
rin gs fu se d tog eth er are
toXJC
srud to possess cancer pro · )
arctnogen IC rty . ze ne (q
► S h Jynuclear hydrocarbons ar prope
uc po e for med on incom I te co b . coJJ
t
<c1,
and petroleu m Pe m us t10 no f or ga ni c m t en.·a ls 1·k tobacco,
·
·
h a I e \vj
► The}' ent er mto uman body and undergovan . ,-{
- - - . --- __ _ _ OUS 6I0c h
,_J
N
· '·
--- em 1 ca1 rea ct · #
- ~ ---- - Ions an d fi lJy dama ge DNA and cau.se
ina ~
 MC ( !} s C o r n er Ext rac ted fro m NCERT
. outcomes
l insight wheth er th e 1ea rning
is com plem enta ry part of the learning process. It gives you a tota
sses sme nt book chap t er, atte mpt t h ese
. ugh the correspond ing NCERT Text
A
qu e
have been achi
stions in exam
.
eved or not. Afte r goin g thro
like environment. Give yourself four
ma rks fo r correct answ er and deduct
one m ar k for wrong answer.
All the Best! ()
that will help you plan you r nex t step.
Atable is given at the end,
each question.
to lates t NCERT pag e num ber{ s) m entioned alon g with
NCERT Connector: To conn ect bett er refer
(b) CH3CH .,C H, -C H - Cl-l 2C H 2 Br
di Classification is a type of :
- - I
CH 3
Which of the foll owi ng men tion ed
J. (c) CH 3CH 2CH.,C H, - CH - CH 3
hydr ocar bon ? - - I
(a) Satu rate d hyd roca rbo n Br
(b) Uns atur ated hyd roca rbo n (d) CH 3C H 2CH 2 - CH - CH.,CH ,
-
(Page301 J
I J
(c) Aro mat ic hyd roca rbo n Br
(NCER T, Pag e 2 95, 296)
(d) All of the abo ve d opr opa ne
8. A mix ture of 1-io d oe th a ne and 1-io
dr y eth er to
lfJ Alkanes is trea ted with sod ium met al and
the fo llowing
carr y out Wu rtz reac tion . Wh ich of
gas is
2. The maj or con stitu ent of natu ral hyd roca rbo ns will be form ed?
(a) met han e (b) pro pan e
(a) Pro pan e+ Hex ane
(c) buta ne (d) hex ane . (Page 296)
(b) Eth ane + Pro pan e
is true ?
3. Which of the foll owi ng stat eme nts (c) But ane + Pro pan e
(a) Sod a lim e is a mix ture of sod
ium hyd rox ide (Page 301 )
( d) But ane + Pen tane + Hex ane
and pota ssiu m hyd rox ide. ium salt o f
rtz reac tion . 9. Wh ich alka ne is pro duc ed whe n sod
(b) Met han e can be prep ared by Wu 3 ?
buta noic acid is hea ted with sod a lime
(c) In alka nes, all carb on atom s are sp
hyb ridi sed. CH 3
(a) CH 3 CH 3 (b) CH 3 CH 2 CH 2
t mon och loro
(d) neo-Pentane yiel ds thre e diff eren (d) CH 3CH 2CH 3
(Page 296, 301 , 302) (c) CH 4
deri vati ves. (Page 301 )
for hyd roca rbon
4. The number of cha in isom ers possible m tem pera ture is
I 0. Hyd roca rbon whi ch is liquid at roo
C5H12 is (b) buta ne
(b) 5 (c) 4 (d) 6 (a) pen tane
(a) 3 (d) etha ne. (Page 30 I )
(Pag e 297) ( c) pro pan e

5. An inhi bito r is des crib ed as 11 . In the give n reac tion s :

s a reac tion B Na ' ether > X Br, y Na. ether Z
(a) a sub stan ce that slow s dow n or stop (1.) CH r 3 hu~
pro pert ies of a
(b) a sub stan ce whi ch inhi bits the
NaO H) X NaOH ) y ~ z
cata lyst ( ii) CH 3COOH CaO hu
tion and doe s
(c) a subs tanc e form ed dur ing the reac Iden tify X, Y and Z.
X Y Z
not part icip ate in the reac tion
n of prod ucts CH 3CH 3
(d) a substance whi ch prev ents form atio (a) (i) CH 4 CH 3 Br
in a reac tion bein g mos t reac tive. (ii) CH 3 C0 0N a CH 3 CH 3 CH 3CH 2 Br
6· Wurtz reac tion is use d to uni te CH 3Br
(b) (i) CH 3CH 3 CH 4
(a) two alky l hali des (ii) CH CO ON a CH 4 CH 3CH 2CH 3
3
(b) two aryl hali des CH 3CH 3 CH 3CH 2CH-'
(c) (i) CH 3CH 2Br
(c) alkyl and aryl hali des CH 4 CH 3 Br
(Page 301 ) (ii) CH 3 C0 0N a
(d) two ben zen e unit s.
(d) (i) CH 3CH 3 CH 3CH 2Br CH 3CH 2CH 2CH 3
7 will reac t with
· Wh ich of the foll owi ng com pou nds (ii) CH 3C0 0N a CH 4 CH 3 Br
Na to form 4,5- diet hylo ctan e? /Pag e 301 302i

(a) CH 3 CH 2 CH 2 CH 2 Br
 wt,tG- Objective NCERT at Your F·
1n9err
. members of the hydroca 01 1

htgherlly formed during reaction s r 600 s ar

198 (a)
genera . i
12. Complete the following reactions :
t hy! free rad1ca 1s may cornbi
Zn - Cu >X (b) two me h ne du
. ation to give et ane tin 11
(i) C2Hsl + H2 C,HsOH . chlonn ~
- Electrolys1s >y 1 loromethane molecules react l
(c) two c1 o fo
(ii) CH 3C00Na + Hp
. Crp/Al20 J ~ z ethane . . . r~
11 ine free radical reacts with rneth
(iii) CH3CH2CH2CH2CH2CH 3 773 K ( d) c 1 or ane
1
give ethane. !Page3 o
c H y- C
(a) X = 2 6' - 2 H6 ' Z = C6H6
r
z _ CH CH 3 . .
. 1 f the followmg 1somenc . eptanes ca .
. h OJI
(b) X = CH ,p y = CH3COOH, - 3 . 18 Whtc, o hl . d nYield
· d'fferent monoc onnate product
(C) ..1X -- C H y = CH z = C,iI-110 seven 1 . . 7 s Upon
2 6' •I> (Page 301, 304) free radical chlonnat10n .
(d) X = C)H6, y = CH-1, z = CsH10
- I (a) 2,2-Dimethylpentane
13 . .rvlatch the column I wi th co umn II and mark the
(b) z-Methylhexane
appropriate choice
(c) 3-Methylhexane
Column I Column II ( d) 2,4-Dimethylpentane (Page JOJJ
(A) 11-Butane~ (i) Free radical
substitution 19 An alkane C6H14 gives t~o monochlor~ derivatives
2-Methylpropane · on chlorination. Its possible structure 1s
(B) CH-1 + Cl2 ~ CH3Cl (ii) Wurtz reaction (a) CH3CH2CH2CHzCH2CH3
(C) RCOONa + soda lime (iii) Isomerisation (b) CH - CH- CH2CH 2CH 3
~RH 3 I
l . CH 3
[(D) :R..tY + N a ~ R- R (iv) Decarboxylat10n
(c) CH3-CH-CH2CH3
(a) (A) ➔ (iii), (B) ➔ (i), (C) ➔ (1v), (D) ➔ ~~~) I
CH 2CH 3
(b) (A) ➔ (ii), (B) ➔ (iv), (C) ➔ (i), (D) ➔ (m)
(c) (A) ➔ (i), (B) ➔ (ii), (C) ➔ (iv), (D) ➔ (iii) CH3 CH 3
(d) (A) ➔ (iv), (B) ➔ (i), (C) ➔ (iii), (D) ➔ (ii)
I I
(d) CH 3 -CH- CH-CH3 (Page303/
(Page 301,303,304)
20. During halogenation of alkanes the halogens and
I 4 . Which of the following has the lowest boiling point?
alkane show a specific trend. Which of the following
(a) 2-Methylbutane (b) 2-Methylpropane
statements is not correct?
( c) 2,2-Dimethylpropane ( d) n-Pentane (Page 302)
(a) The reactivity of halogens is in the order
CH3
F2 > Cl 2 > Br 2 > 12 .
15. In the following reaction, 6 ~; ) (b) For a given halogen the reactivity of hydrocar·
hon is in the @rder of 3° > 2° > 1°.
the major product obtained is

(a) 6,B, (b) 68, ( €:} Bromine is less reactive than chlorine towa rds·
a particular alkane.
( d) On chlorination monosubstituted pro~uct 1~
formed while on bromination disub 5t1tute
.

(c) 6
CH3
Br (d) 6__
CH3
21. Chl ·
products are formed.
· of alkanes is a photochem1c
onnation
(PageJOJI
· al process-
Br It is initiated by the process of
(Page 303)
16 . In the reaction, Cl 2 +CH 4 ~ CH Cl + HCl ( a) heterolysis (b) homolysis eJOJi
3 k) pyrolysis (d) hydrolysis. fP09 .
presence of a small amount of oxygen
0
(a) increases the rate of reaction for a brief period 22. Wh1· h · cham· propagation step m · the followillo
c step 1s
of time mechanism?
(b) decreases the rate of reaction for a brief period
of time (i) Clz~Cl+ Cl
(c) does not affect the rate of reaction (ii) Cl+
•
CH 4 ~ CH 3 + HCl
(d) completely stops the reaction.
(Page 303) (iii) Cl + Cl ~ Cl
• 2
17. Ethane is formed during the formation of chloro- (iv) CH3 + C l ~ CH Cl
methane by chlorination of methane because 3
(a) (i) (b) (ii) (c) (iii) (d) (iv) oJ:
(Page3
 cwnis try I Hydrocarbons
Which one of th e foll ow in g give ., unly o ne
23· rnonochloro derivative?
(b ) n-f-l cxa nc
(c1)
(c)
lk 11zc nc
p,,J yli e: pt anc
(b1 ·rulutrn:
Id) ( ,y<.l r,lwp l ,w<:
199
-
(a) neo-Penlane ,JI

(c) 2-Methylp ent ane (d) J -Mc th ylpl' 11l ,in c U' I Al ken o ~
If It.JI' I(/ Ii
I , l ,'1,7 < ) 1 l.111· 1 r.i< ' l ll' ( ,,,,1,1 11 1•, X rr br1n d, ,1r,J
y
Ma tch th e co lumn with co lumn II t n iden tif )' l>11nd •, ·x· .i11d ' Y' Jr ••
1{
r1", f JI I IJ 11·1,
2-!,
the produ cts of oxidati on of a lb nc,, and nm,
k t il l· I ~. 'i rd J 1 ~, L
(" ) 2 \ ,, ( I, J I 7 •I /, J
:ippropriatc choice. ,I
--- - Colu mn J Colu mn II HJ. ( ;t' ( J l) ll ' l 1 l, .il 1',1)Jll (• r, •,Jr, I ', c ,111 •, 1·,J

( :1)by r n lr i t l cd rr1t ;i [1 1111 ,Hou nd( , r , iJr)n<l

( i) I ICO( ) lf I lf 10
( b) by I hl' p r<.: '>e l h e r1f 011c ,1 •,y 1nrrJl 'I rJ L , -:1rb,,n
d l <1m
1,1 the •,amt
l'u 5~ ' ~ (L) du e l o til e Jd l<:rcnt grriup•, ;i ll ,1(.h ,·d
( ii ) (C l I 1 )i C O II
(B) 2CH ,1 +O J -,-() {-
) ,-
, ll-11~ fun cti ona l gruuµ
ltnt
- - - - \1 ,,,u , (d) by '> win g of hyd m gc:n atom between twoI d1·1a
tCl CH~+ O" -~ ( iii ) 2C I 110 11 a l O lll ', ,
r

, {C l I 1n XJ): M t1 .11, ·1li e a lkenc: th at cx hibih gccimctri ca l 1

,omeno:,m ;., 1

(D)C H-l ~ ~O: - - - -- (iv ) HC HO t- 1l l )

(a) prop cnc (b) 2-mcthylpropen c
(i), (B) ➔ (ii ), (C) - ~ (iii ), (D) ➔ (iv) (c) 2-bu tene (d) 2-mt t hyl-2-butene.
(J l (.·\ ) ➔
rPu.J~ /j ,
( ii ) , (B) ➔ (iii ). (C) ➔ (iv), (D) ➔
(i )
tb) ( :\ ) ➔
(i,·), (B) ➔ (ii ), (C) ➔ (iii ), (D) ➔ (i) for the
ld (:\ ) ➔ 32. How many geom etri cal isom ers are poss ible
( iii ) , (B) ➔ (i), (C) ➔ (ii ), (D) ➔
(iv)
(J) (.-\ ) ➔ given com poun d ?
(Page 303, 304)
CH 3 - CH = C H - C H = CH - C 2 H 5
the (b) Thre e
:_~. Fe\, reac ti ons of alka nes are gi ven. Iden tify (a) Four
(Page 308, 3091
ctly matc hed (c) Two (d) Five
name of the reaction wh ich is not corre
\,i th th e reaction . 33 . Whi ch of the follo wing com poun ds
will sho w
CH 3
AIC13 ..,.. HCI
I cis-trans isomerism?
CH 3 -CH -CH 3 (a) (CH 3 ) 2 C CHC 2 H 5 =
773 K
- Isom erisat ion
(b) H 2C CCl 2 =
(b) C6 H 14 ---- C 4 H 8 + C 2H 6 - Pyrolysis (c) CH 3 HC = CCIC H 3
(c) CH4 - 201 -4 CO .J.. 2H 0 - Controlled oxidation
2 2 (d) HCIC = CH 2 (Pa ge 309)

(d) CH4 - HN0 3

4
oooc > CH 3N0 2 - Nitra tion 34. 2-Br omo pent ane is treat ed with alcoh
olic KOH
in
(Page 303, 304) solution. What will be the major product formed
?
dark this reaction and what is the type of elimination called
26. Chlo rination of meth ane does not occu r in
(a) Pent-1-ene, ~-elimination
because
of (b) Pent-2 -ene, ~-elimination
(a) methane can form free radicals in presence
(c) Pent-1-ene, nucleophilic subs titut ion
sunlight only
cules (d) Pent-2-ene, nucleophilic subs tituti on
(b) to get chlo rine free radicals from Cl 2 mole (Pag<' 31 0'
energy is requ ired. atoms
in 35. Wha t is the orde r of reactivity of hydrogen
(c) subs titut ion reac tion can take plac e only
attac hed to carb on atom in an alkene?
sunlight and not in dark (b) 2°> 1°> 3°
. It (a) 3°> 1°> 2°
(d) termination step cann ot take place in dark (d) 1° > 2° > 3° 1Pvgc 370 l
(Pnge 303) (c) 3° > 2° > 1°
requires sunl ight. estio 11 s
27. Kerosene is a mixt ure of Read the pass age give n below an<l a m wcr th e qu
(Q . 36 -38 ) that follo ws :
(a) aromatic hydr ocar bons gen
(b) aliphatic hydr ocar bons Dehy droh aJog enat ion involves removal of the halo
carb on
(c) unsaturated hydr ocar bons atom toge ther with a hydrogen atom from a
l,olic
(d) saturated hydr ocar bons . (Pag e 301) atom adjacent to the one with halogen atom. Ako
to
28 when KOH is used for dehy droh alog enat ion. According
· Which of the following prod ucts is form ed ed, the
yst Saytzeff's rule, whe n two alkenes may be form
n-heptane is passed over (Al 20 3 + Cr 20 3) catal r prod uct.
alkene which is most subs titut ed is the majo
at 773 K?
 ,, v- - u' YUlJ rF 1nge~

CH CH2CH2CH == CB2, I~\

X - CI-l3 z ) CH

200
h
.
following a .
decreasing
lkyl halides in . n with
reactto
(c) y: cJ-I/HCOH2(;I) = 3CH3(CH2) 2Clio
- HC '
36. Arrange t e of p-eliminat10n (I) - . -C == CH-Cl-1 ,
order of the rate -1- Cl-l3 X:::: CH3CH2 I 3
al coholic KOH . CH _ Cl-1 - Cl 1
(d) CH3
Cl' Br 2 .l
CH3CH]Cl-l2Br I - -•2
CH .l - Cl-I Rr
- CH (CH2hCH3,
Ct-13 (iii) } CHO,
YI)- :::: Cil3 · (II) = CH 3CH 2CH0
(
(i) ( ii) (b) (iii) > (ii) > -~i)
(Page 310
(a) (ii) > (iii) >.~!) (d) (ii) > (i) > (1ti) . . ,J1i,
c
ior the follow111g react10n s are
(c) (i) >( ii) > (111) (PO(Jd 70) The procILicts
ti} , Br
. . r different
Th e ease of dehyd ro I1a Io~t ' 11 0 1 urn to

CH3-yI -CH 2-Cl-1 3

37. I r +ale. KOH ~ X
halogens is in the o rCt' I 'd , (i)
(a) iodide > brom1'd c~ ,,.... d1 on'd t
. d 1'd t, > chlon e H 0
(b) bromidt' > 10 . . , 3
~ Y+ z
(c) chlorick > h ronuc .,. · le , 1od1d1::
. /PageJ I OJ
I -cH~CH2
(ii) Cl-f3- Cl-l
. ·I1I 'd > bromide. .
(d ) iod ide > "- on e , . tion of • CH 3
38. What art' the• products of d eI1ydroha 1og1::n<1 •
(a) X = (CH3)2C = CHz, y = CH3CH2CH0,
2- Iodopentane? (minor)
( a) · ), 1-Pentene ( . r)
') -Pentene ( ma1or Z = CH3CH2CHO
? Pentene mmo
(b) X= CH2_- CH2' y = CH3CHO, Z == CH3COOH
(b) -1-Pentene (ma1or · ) ' -- )
(c) 2-Pentene (sow ) I Pentene (50%
,o' - (Page 3 10) (c) X = CH3-CH=CH-CH3,
(d) None of these .
CH3
The compound formed when alcoholic soldut1?n ~f I
39. ethdene dibromide is h eate d WI.th i:,!ITallulate zmc 1s Y= CH3-CH-CHO, z = HCHO
(a) ' ethene (b) e th yne (d) X = CH3 - CH= C(CH3)z, y = HCH0,
th (d) bromoethane.
(c) e ane (Pdge 31 0) z = CH3CHO (Page 310,3111

Pent-1-ene with HCI gives

cone. H2S0~ A Cl2 ) B.
-!O. CH3 CH2CHpH
170
cc soo c 0 44. (a) 3-chloropentane (b) 2-chloropentane
A and Bare (c) 1,2-dichloropentane (d) 1-chloropentane.
CH3CH2CH3, B = CH3CH2CH2Cl
(a ) A = (Page 31 1)
(b) A= CH 3CH = CH 2, B = CH 2ClCH = CH2 45. Presence of unsaturation
. m . orgam·c compounds can
(c) A= CH 2 = CH 2, B = CH 3 CH 2Cl be tested with
(d) A= CH 3CH 2CH 3, B = CH 3 CH CH
2
. = (a) Fehling's reagent (b) Tollens' reagent
(Page 3 10)
(c) Baeyer's reagent ( d) Fittig's reaction.
4 I . An alkene X is obtained by dehydration of an
(PageJIii
alcohol Y. X on ozonolysis gives two molecules of
46.
ethanal for every molecule of alkene. X and Y are Which of the following reactions does nots howthr
(a) X = 3-hexene, Y = 3-hexanol correct products of the reaction?
(b) X = 2-butene, Y = 2-butanol (a) CH 3 - CH= CH 88 :d )
(c) X = I-butene, Y = I-butanol
2
perox1 e Br

(d) X = I-hexane, Y = 1-hexanol. (Page 3 10,31 3) CH3 - CH2- CH1

42. An organic compound C6H 12 (X) on reduction gives
(b) CH3 - CH= CH2 HCI >
peroxide Cf-LCI
C6 H14 (Y) . X on ozonolysis gives two aldehydes CH3 - CH2- .
2
C H 40 (I) and C4H 8 0 (II). Identify the compounds
X, Y and aldehydes (I) and (II). Br
= (c) CH3 - CH= CH I CHJ
(a) X == CH3CH CHCH CH CH ,
2 2 3 2 HBr > cH 3 -CH-
Y = CH 3(CH 2) 4CH ,
3
(I)== CH3CHO, (II)== CHiCH2)2CHo
(d) CH3 - CH= CH
2 HCI ) CH 3 -yH- CH;
(b) X = CH3CH 2CH CHCH CH = Cl 31i'
~ CH,CHo, (II) ~ CH,CHo
2 3> 1I,
y ~CH,(CH,),CH,, (I) 47. (Page 3 {
eo
The react' · d' t sand t}'P 1
terms of interme ia e top tiD1'
re t' · ton in
ac ton ts given below. Mark the incorrec
 cherJllS
. rry I Hydrocarbons
CH 3
I =
b
CH 2 + HB r ~ Carrme
.
ocat100
(a) CH 3CH , -C =C H- CH 2CH 3
- I
CH 2CH 3
201
-
CH 3-C inte diat e C f-½C H3
(a)
CH 3 H
I
(b) CH 3CH 2- CH = C H -C H-C 3
I Peroxide Free radi cal
) inte rme diat e CH ')CH 3
(b) CH 3-C =C H2 + HB r I -
(c) C H 3 -C = C- CH
. . ._,_ C/ X Elec trop hili c I 3
(c) /C = '.. + 2 ~ sub sti tuti on
CH 2C H 3
.....__ / CH = C H - CH 2C H 3
(d) /C == C'. . + 0 3 ~
Ozo nide (d) CH 3CH 2C H 2CH 2 -
(Page 311 , 312, 3 13) (Page 313)

A compound X decolourises
Br 2 water and reacts so. An alkene, 3-Eth ylpent -2-e ne wi ll give wh ich of the
give an addition product. ?
~B. slowly with cone. H 2SO 4 to following produ cts on ozonolysis
X reacts with HBr to form Y. Y
reacts with NaOH (a) HC HO + CH 3CH 2CH 2CH O
hex an- 3-o ne. CH 2 -C H 3
to form Z. On oxi dat ion Z gives /
== C'---..
reactions are (b) CH 3CHO + 0
,\v , y and Zin the CH 2 - CH 3

X Br1 wate r Dec olou risa tion

lcone . H2S04
(Page 3 13)
Addition pro duc t
CH 51. An uns atu rat ed hyd roc arb on
was tre ate d wit h
X~ Y NaO H) Z ~ CH 3CH 2CH 2 -CII-C H 2 3 hydrolysis gives
ozo ne and res ulti ng ozo nid e on
0 de. Wh at is the
Hexa n-3-o ne 2-p ent ano ne and ace tald ehy
CH CH 3, = stru ctu re of alkene?
(a) X = CH 3CH 2CH
CH 3, (a) C 3 H 7 - CH = CH - CH 3
Y = CH 3CH 2 CH (Br )CH (Br )CH 2 /H
C3H 7,
Z = CH 3 CH 2 CH 3
(b) CH 3/C =C ,CH 3
(b) X = CH 3 CH CH CH 3 , = , - /CH 3
Y = CH CH (Br )CH (Br )CH 3 , CH 3, - C /C2 Hs (d) C3 H7 C C
3 (c) C 'CH 3 CH 3/ - 'CH
CH 3/ - 3
Z = CH 3CH 2CH 2 OH (Pag e 313 )
(c) X = CH 3 CH 2 CH =
CH CH 2 CH 3 ,
-1- ene gives
52 . Hydrolysis of ozo nid e of but
Y = CH 3C Hz -CH -CH zC Hz CH 3, eth yle ne onl y
(a)
I
Br ace tald ehy de and formaldehyde
(b)
e
Z = CH 3C Hz CH 2- CH -CH zC H3 pro pio nal deh yde and for ma lde hyd
(c)
I (Page 3 13)
OH ace tald ehy de only.
(d)
CH CH 3 , = , 53. Oz ono lys is of 2,3 -di me thy lbu t-1 -en e followed by
(d) X = CH 3 CH 2 CH 2 CH es
red uct ion wit h zinc and wa ter giv
Y = CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 Br, d
(Page 311 , 3 13) (a) me tha nal and hexanoic aci
Z = CH 3 CH 2 CH 2 CH 2 OH
(b) me tha noi c aci d and bu tan one
49. Propan-1-al and pen tan -3-
one are the ozo nol ysi s (c) me tha nal and 3-m eth ylb uta
n-2 -on e
is the str uct ura l thy lbu tan oic aci d.
pro duc ts of an alk ene . Wh at (d) but ano ic acid and 2,3 -di me
(Page 313 )
formula of alkene?

. Alkynes
ma rk the appropriate choice.
54 col um n I wit h col um n II to give the cor rec t IUPAC nam es and
· Match the
- lumn II Co
I j!J Co lum n I
CH iCH 2)4 -C H - (CH 2)3CH 3

{;
(i) Pen t-l- en- 3-y ne
I
CH 2-C H( CH 3)2
( ii) 4-Ethyl-1, 5-~~P.:.~-~-~e-~~- -----····· --·--- -----____ ---
( ) CH 2 == CH -C -C -C H3
- -- ---- -- --- -- ------- ------ ------ --- --- -- --- --- -- --- -- - -- --- --- - -- --- --- -- -- -------- --
I. . . ·-
-- ---- ---------- ----- ------ -----------
 W\.t G- Objective NCERT at
202 Your Fi
------ -- -- ----- --- -- --- -------------- -- ------- --_______ __ __ nge~ips
·- ....
(iii) 5-(2-Methylpropyl)decane I

(iv) 4-Phenylbut-1-ene

(b) (A) ➔ O-v), (B) ➔ (ii), (C) ➔ (iii), (D) .

(a) (A) ➔ (i), (B) ➔ (iv), (C) ➔ (ii), (D) ➔ (iii)
(d) (A) ➔ (ii), (B) ➔ (iii),(C) ➔ (i), (D) ~ _(1)
(c) (A) ➔ (iii), (B) ➔ (i) , (C) ➔ (iv), (D) ➔ (ii) ~ (iv)
(Page 297 3
, 07 31
(c) Ethyne is formed. ' 11
55. Choose the correct reagents used in the conversion.
(d) Ethene and ethyne are formed.
CH2 == CH 2 ~ CH., - CH 2 ~ CH 2 == CHBr !Page316
1
1 1 - I 60. One mole of 1,2-dibromopropane on t reatni
Br Br with X moles of NaNH 2 followed by treatrn ent
~ CH=CH -"4@ (a) one (b) two (c) three
ent Vi h
ethyl bromide gave 2-pentyne. The value of X. it
(d) c
18
t0Ur.
p q r s
(Page 316/
(a) Br 2 ale. KOH NaOH Al2O3 61. The most acidic hydrogen atoms are present in
(b) HBr ale. KOH CaC 2 KMnO 4 (a) ethane (b) ethene
(c) HBr ale. KOH NaNH 2 red hot (c) ethyne (d) benzene. (Page
3161
iron tube
62. Which of the following alkynes is most acidic?
(d) Br2 ale. KOH NaNH 2 red hot
iron tube
(a) CH 3C == CH (b) CH 3C CCH =
(c) CH 3CH 2C == CH (d) CH= CH /Pa!e3161
(Page 31 O, 311, 316, 318)

56. Which of the following does not c@rrectly represent 63 . The correct trend of acidic nature of the followin
alkynes is g
polymerisation of alkenes and alkynes?

o
(a) CH== CH> CH 3 - C== CH > CH 3C=CCH3
( a) nCH == CH ~ -f CH= Cffi - CJ;I = CH t,, (b) Crl3 - C ==CH> CH== CH> CH 3C = CCH3
(b) 3CH=CH ~ (c) CH 3C-CCH 3 > CH3 - C== CH> CH=CH
(d) CH == CH > CH 3C - CCH 3 > CH 3C = CH
(Page 316!
(c) nCH 3 -CM=CH 2 ~ -f?H-CH21z
64. IdenHfy the reagent which can easily distinguish
CH 3
between 1-butyne and 2-butyne.
( d) nCH 2 == CH2 -? -f CH2 - CH= CH - CH2tn (a) Bromine water (b) Baeyer's reagent
(Page 31 4,317,31 8) (c) DiluteH2SO4 +HgSO4 (d) Ammoniacal CuiC'2
(Page 316/
5 7. H@w many strsuctures are possible for C 5 H 8 with one
triple bond? 6 5. Which of the follpwing alkynes can be identified
(a) 4 (b) 3 (c) 2 i(d) 1 and distinguished from the rest of the alkynes on
(Page 31 4) reaction with ammoniacal silver nitrate?
(a) CH 3C=C-CH 3 (b) CH 3CH 2C::=CH
58. Identify X ancd Yin the foll0wing reaction.
(c) CH3CH2C=CCH3
HzC - CH2 + KOH alcohol X NaNH2 y (d) CH3C=CCH CH CH (PageJ16!
2 2 3
I I
Br Br 66 · Which of the following reactions does not shovi the
X y acidic nature of ethyne<. d'1UJll
(a) CH 3CH 2Br CH 2 =CH 2 (a) Acetylene reacts with sodamide to form so
(b) CH 2OH - CH 2OH CH 2 =CH 2 acetylides.
(c) CH 2 = CHBr CH=:CH (b) When passed through ammoniacal cup roos d.
(d) CH== CBr CH == CH (Pag e 3 16) chloride solution, a red precipit~te is
(c) Acetylene reacts with chlorine 1n the
10 f~!
59 . What happens when calcium carbide is treated with
water? form di or tetrachlorides. fljaC~
0
(d) 1:-cetylene when passed through a.rnfil
(a) Ethane is formed.
silver nitrate gives a white precipitate.(POge 316!
(b) Methane and ethane are formed.
 203
chemistry I Hydrocarbons

0
reaction : Cl-lr lr
f i . Identify the prod uct for the following
CH: :: CH + HOC l ~
(a) Cl 2 CHC HO (b) CH( OH) = CHCI (b) 2 4- Brnmo- 1,1-d ih rnmo - l
(c) CICH 2CH2OH (d) CH 3COCI Br phcn ylmc lh anc
iden tifyi ng
. com plet e the follo wing reac tion by
68
Xand Y.
c H CH2C =CH
3
NaNH ,
-> X

(a) X = CH3CH2COO Na, Y = CH 3CH 2CH

(b) X = CH3CH2C =
C H B
2

CH 2
CNa , y = CH3CH2C CC2Hs
s r> y

=
= (c) 0 Cl

Cl-13
C hl orn -1-ph enyl meth an c

(c) X = CH3CH2CH 2CH 2Na, Y = CH~

CH 2CH 2CH 3 Cll 2Cll 2CI

(d) X = CH 3CH 2CH CNa , =

Y = CH 3CH 2 -CH -CH 3
I
C2Hs
(d)
O I-C hl oro -2-p heny lcth ane

7 4. The corr ect stru cture for triph enyl

brom ome than e is
(ParJP 3 18)

O t- 0
Br
(Page 3 16)

omo prop ane (a)

69. Which o~the f~llowing will give 2,2-
dibr
on react10n with HBr?
(a) CH3 - CH = CH 2 (b) CH 3C = CH 6 - e,
(c) CH 3CH =CH Br (d) CH =C H
OCH,--Q
(Page 3 17J
0,
tion with the (b)
70. When 1-bu tyne und ergo es oxy mer cura
ed is/are
help ofHgSO 4 + H 2SO 4 , the product(s) form Br
(a) CH 3CH 2COO H + HCO OH
(b) CH3CH 2COC H 3
(c) CH 3CH 2 CH 2 COO H
(Page 31 1) (c)
(d) CH 3CH 2 CH 2 CHO
i l. Ozonolysis prod ucts of 2-pe ntyn e
afte r deco mpo si- Br
ent oxid a-
tion of ozon ide with wate r and subs equ
tion are (d)
(Page 318)
(a) etha noic acid and prop ano ic acid
(b) etha noic acid and prop ano ne 75. Coa l tar is the mai n sour ce of
(c) etha noic acid (a) arom atic com pou nds
(d) formic acid and glyoxal. (b) alicyclic com pou nds
reac tion (c) alip hati c com pou nds
72. The ozonolysis prod uct( s) of the following (Page 321)
is(are) (d) nitr o com pou nds.

CH 3CH2 -C = CH (i)
03
(ii)H P
> Product(s) 76. Alth oug h ben zene is high ly unsa tura
ted it does not
und ergo add ition reac tion s. The expl anat
ion of this
(a) CH 3 COC H 3 can be sugg este d as
calis ed
(b) CH 3COC H 3 + HCH O (a) 1t-e lectr ons of benz ene ring are delo
pres ent insid e the ring ,
(c) CH 3CO OH + HC OO H (b) sinc e 1t-e lectr ons are
CH 3CH 2 CO OH + HC OO H addi tion cann ot take place
(d) add itio n
(c) cyc lic stru ctur es do not sho w
IIJ Aromatic Hydrocarbons reac tion s
( d) ben zene is not a reactive com pou nd.
(Page 321)

73· Whi ch of the foll owi ng nam es is not corr ectl y th in benz ene?
77. Wha t is the carb on-c arbo n bon d leng
matched with the com pou nd? (a) 1.20 A and 1.31 A (b) 1.39 A
(c) 1.39 Aand 1.20 A (d) 1.20 A
(Page321 J

6
CH 2CI
pou nd whi ch
78 . Iden tify the poly nucl ear arom atic com
(a) 1-Chloro- l-phenylmethane
is arom atic .
 lrfYrJrocart
W1.,-t;G- Objective NCERT at your Fin ·,tf'/J I bla
cnef11' V' :.t.1. tbe i.. a
9err1 •~ e ll
d chl ori nat ion o f ben zen e are
Pi
. tion an lic and e l ect rop hil i c sub . fl fl g;e~ bel l
204 84. N1tra I phil st,tur 99- ~e s iJ'l 0 f
(a) nuc eo. t@~ re

w cco c8
'01
/2
res pec tive y
nuc leo phd
.
1
.
c sub . \ Jilile;tlll 111--
hili c and st 1tut ••,s ----
ssJnow, -
1/ 1/ --.;: :--.; ::'-: : (b) ele ctro P 1on
if'l pr·
I I ✓,;: res pec tive ly
in bot h the en°J1
oph ilic sub stit utio n ~
,erof0
(ii i)
. . . b reaq · I
(11)
(c) el ec t r e r 'on 1
~!!i) th
(i)
ilic sub stit utio n 111 oth
(b) (ii) and 1 oph eaqi on1 a l:z J(el
(a) (i) and (ii) (d) nuc e
(c) (i), (ii) and (iii) (d) (i) and (111) (Pag e 32 1J .
The foll ow ing rea ct1 0n 1s now
• k n as
/Pa
9~J1
·
11 (a)
sf' oe
AICl3 C H CH (w) sp 3
La •
85.
cies ~ aro ma tic o?I CH Cl > 6 5 3 + HCJ
(c)
Sf' :z 13a
79. Wh ich of the following spe c6
H + (anh y.)
I 3

(a) o+
\ I
(b) ~
~
..
(c) 0\ -
(d) o
..
6
(a) Wu rtz- Fit tig rea cti~ n
(b) Fri ede l-C raft s rea ct1 0n
(d) Sf'

t-Jitr:aUO
11 . of
(Page 321)
(c) Ro sen mu nd rea ctio n 90. sen ce
. s d o es not sho w !Page Ji11 i.ll p,11e ·d
. g spe cie
80. Wh ich of the foll owm (d) San dm eye r rea ctio n. ·s to p,r@Vl
aromaticity? den tify (A), (B) a nd ( C) . I ) nuc leo

(a) 0 S
(b) 01
~N
(c) (J N
H
(d) □
(Page321 )
86. I

w~◊~(~ 02
B)Jg_,~~
CH
3 CH CN (a
fb) free ra
(c) e}ectrc
(e) €at aly:
·· u
~ A I C l3
em ent from the following. In haloge n;
8 1. Ma rk the inc orre ct stat Cl, C ➔ NaCN
A ➔ CH 3 CO C1, B ➔ C 6 H 5 91 . . .
(a) u
(a) Benzene has a pla nar stru ctu re. Cl, C ➔ KCN car,rier 1s
roc arb on and (b) A ➔ CH 3 Cl, B ➔ C 6 H 5CH 2
(b) Ben zen e is an uns atu rate d hyd Cl, C ➔ AgCN main fu.n ct
shows add itio n rea ctio ns like alke nes. (c) A ➔ CH 4 , B ➔ C 6 H 5 CH 2
use s two p-o rbi tals for A ➔ CH 3 Cl, B ➔ C 6 H 5 CO
C1, C ➔ KCN (a) X
(c) In ben zen e, car bon (d)
(Page 32))
hyb ridi sati on.
high percentage in the following sequence
(d) Aromatic hydrocarbons contain 87. Ide ntif y (A) , (B) and ( C)
ty flame. 92. Wfu.i€h@f
of car bon hen ce bur n wit h soo of rea ctio ns.
(Pag e 320, 32 1, 322) of ele ctF O/
82. Ben zen e easily shows
> (A) ~ (B) ~ (C)
(a) ring fission rea ctio ns sinc
(b) add itio n rea ctio ns since it
(c) ele ctro phi lic sub stit utio
e it is uns tab le
is uns atu rate d
n rea ctio ns due to
HN03
H2 SO 4
(50° C)
FeB r HCI
3
(a)@
stable ring and hig h 1t elec tron
den sity (a) A ➔ Nit rob enz ene , B ➔ Din itro ben zen e,
utio n rea ctio ns due to C ➔ p- Bro mo ani lin e
(d) nuc leo phi lic sub stit
(b) A ➔ C 6H5SO 3H, B ➔ m-B
tron density. enzenesulphonic acid,
stable ring and min imu m elec
(Page 32 1, 322) C ➔ m- Be nze nes ulp hon ate
(c) A ➔ C 6 H 5 N0 2 , B ➔ m-B
owi ng rea ctio ns : romonitrobenzene,
83. Ide ntif y A, B and C in foll
OH C ➔ m- Bro mo ani lin e
(d) A ➔ p-N itro ben zen e, B
➔ m-Trinitrobenzene,
(i) @+A disrnl. ➔ @ 88
C ➔ m- Bro mo ani lin e
· Co mp lete the rea ctio n wit
/Page Jlll

h sui tab le reagents anJ

(c) ~
com pou nds .

+B
CH 3

0H ~ o 01 G
O
>
~
0
(ii) JS0-2oo•c oxi- (D)

l;::) (A) 1/"' :-....

HCJ, hig h'" """ ~ j dati on) (B) NaO H) (C )~ (cl)
AICJ 3 ::::--...

Cl
O,
(a) (A) - CH4, (B) - C 6H 5CH
(i ii) @ ( C) - C6H 5CO ON a, (D) - CH 4
(b) (A) -' CH3Cl, (B) - C 6H 5
CO OH ,
KOH
(a) A =Ni, B = H2 0 (liq uid ),
C = H2 0 ( C) - C6H 5 CO ON a, (D) - ale.
(b) A= Zn, B H2 0 (ste am = ), C LiA IH = (c) (A) - CH3Cl, (B) - C 6H 5CO
OH ,
), c = HC!
4
OH + caO
(c) A= Mg, B =H 20 (liq uid ( C) - C6 Hs CO ON a, (D) - Na
=
(d) A= Sn, B H 20(b oili ng)
c Cl =s ,,3121 ,
(d) (A) - CH 3coc1, (B) - C 6 5
H CH 0,
n 2 (Pag e 322) ' 32
l /Page
(C) - C6 Hs CO ON a, (D ) - A1C 3
 205 1
. try I Hydrocarbon s hyd rogenated.
CherJliS (IV ) C 6 H 6 is catalytically
words.
f'Il in the blanks with app rop ria te II III IV
e. All car bo n I
zene has a pla na r str uc tur
1
s9- d Th . (a) Chl oro - To lu ene Nitro - n- He xan e
rid ise . e rin g
wms in ben zen e are _ I _ hyb
Ben
II . It me tha n e benzen e
a ucture of ben zen. e wa s pro pos ed by ·th
b stit utt on react10ns . t _reac t s w1
. . I (b) Me thyl - Chl oro - Phe n yl Trim ethyl -
str
sho ws _l lL su
to for m ben zen e ben zen e nit rite ben zene
I rv: in pre sen ce of alu mi niu m chl ori de To lue ne
11 ' ~
,eto phe non e. (c) Benzyl Tri me thy l - Tri nit ro-
I III IV tol uen e
a I II ch lor ide ben zen e
ele ctr oph ilic ace tyl chl ori de Cyclo-
'1 I
(a) sp2 Kekule (d ) Tol uen e Aceto - Tri nit ro-
nuc leo phi lic chl oro me tha ne
(b) sp De wa r phe non e ben zen e hex ane
(c) 5p3 Lad enb erg ele ctr
oph ilic chl oro eth ane (Page 322 , 323 , 324)
(d) p2 Baeyer nuc leo phi lic me thy l bro mi de
5
(Page 319, 320, 321 , 322, 323
) h col um n II and ma rk the
94. Ma tch the col um n I wit
out wit h cone. HN 0 3 app rop ria te choice.
Nitration of ben zen e is car rie d
I

90 e rol e of con e. H 2 S0 4 Co lum n I Co lum n II I

· in presence of con e. H 2 S0 4 . Th
(A) Alkyl hal ide + So diu m (i) Sul pho nat ion
is to provide
cti on
(a) nuc leo phi le dur ing the rea in pre sen ce of dry eth er
rea cti on
(b) free rad ica l dur ing the (ii) Wu rtz rea cti on
rea on
cti (B) Ar ene + Ac id hal ide in
(c) ele ctr oph ile dur ing the pre sen ce of AlC1 3
ctio n. (Page 323 )
(d) catalyst du rin g the rea (iii) Ca taly tic
roc arb on, a hal oge n (C) Ar ene + Fu mi ng
91. In halogenation of aro ma tic hyd sul phu ric aci d hyd rog ena tio n
lly a Lewis acid. The
carrier is use d wh ich is gen era (iv) Fri ede l-C raf ts
to gen era te the species (D) Ar ene + Hy dro gen in
main function of thi s rea gen t is • rea cti on
(d) X pre sen ce of Ni
(b) x- (c) x+
(a) X (C) ➔ (ii), (D ) ➔ (iv)
323)
(Pa g e
(a) (A) ➔ (i), (B) ➔ (iii ),
(C) ➔ (iii ), (D ) ➔ (i)
l I
cti ons is no t an exa mp le (b) (A) ➔ (iv), (B) ➔ (ii) ,
92. Which of the fol low ing rea (c) (A) ➔ (iii), (B) ➔ Ci), (C)
➔ (iv) , (D ) ➔ (ii)
zen e rin g?
of electrophilic sub stit uti on in ben (d) (A) ➔ (ii) , (B) ➔ (iv),
(C) ➔ (i), (D ) ➔ (iii)
(Page 30 1, 322, 323, 324)

@+c1
(a) 2 A IC I, >~ 9 5. Wh ich of the fol low ing
ste ps is no t cor rec t in the
me cha nis m of ele ctr oph ilic
sub stit uti on of ben zen e?
ile lik e x+, R+, No ;, etc.
(a) Ge ner ati on of ele ctr oph
ult ing in the for ma tio n
(b)@ + CH 3COCI --➔7 ~
AIC I,' 60COCH3
(b) Att ack of ele ctr oph ile res
of are niu m ion in wh ich on
sp3 hyb rid ise d.
e of the car bo n is

Cl ben zen e rin g to giv e

(c) Ad dit ion of pro ton on

(c) 0 + JCl2 '""h ght > CJ~CI

car bo cat ion .
(d) Re mo val of pro ton fro
3
m sp car bo n ato m to

V Cl~CI
Cl
res tor e aro ma tic cha rac ter .
(Pag e 323 , 324 )

S0 3H sub sti tut ion rea cti on , the

96 . In ele ctr oph ilic aro ma tic

(d) @+H 2 so4 ~@ nit ro gro up is meta dir ect ing

(a) dec rea ses ele ctr on den
bec aus e it
sit y at meta po sit ion
sit y at meta po sit ion
(Pa ge 322, 323 , 324)
(b) inc rea ses ele ctr on den
sit y at ortho an d para
( c) inc rea ses ele ctr on den
93 fol low ing rea cti ons .
· Name the pro du cts of the po sit ion s
l chl ori de in pre sen ce sit y at or tho an d para
0) C6H6 rea cts wi th me thy ( d ) dec rea ses ele ctr on den
(Pa ge 325 )
of AIC1 3. po sit ion s.
chl ori de in pre sen ce of gro up s is o,p -di rec tin g
(II) C 6H6 rea cts wi th ace tyl 97 . Wh ich of the fol low ing
AIC1 3. h il ic
rin g for ele ctr op
nit ric aci d in pre sen ce bu t de act iva tes be nz en e
(fll ) C 6H6 rea cts wit h fum ing sub stit uti on?
c H, SO •.
 206
(a) -CH 3 (b) -NH 2
(c) -Cl (d) -N0 2 (Page 325)
9 s. The correct order of reactivity towards electrophilic /
substitution is ! (a) x = Triozonide, Y = Glyoxal
(a) benzene> phenol > benzoic acid> chloroben- / (b) X = Diozonide,_Y = Succinic acid
zene / (c) x = Mono0zomde, Y = Benzo·ic acid
. .
(b) phenol > benzene > chlorobenzene > benzoic (d) x = Tnozomde, Y = Benzaldeh yde
acid
(c) chlorobenzene > benzoic acid > phenol > - Carcinogenici ty and Toxicity
benzene
(d) benzoic acid > chlorobenzene > benzene > 100.1, 2-Benzpyrene is
phenol. (a) a polynuclear hydrocarbon
99 (b) carcinogenic in nature
. Similar to alkenes and alkynes benzene also
undergoes ozonolysis. In the sequence of the given (c) an aromatic hydrocarbon
reaction, identify X and Y. (d) both (a) and (b).
(PageJ;:

C~ck Y~r score! If your score is

- ~~ EXCELLENT !
01
~ ~
-~e on to the next ch c~I
95~85_%_] on your fingertips. apter. You have mastered this chapter. Concepts are
- -- - VERY GOOD !
- Revise once more th tlteJ11- tdJ
ii-~-si l
0
GOOD! will master this ch oroughly. Recognise your mistakes and work on
apter.
. .. i<il