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(a) (A) (), (B)- (ii),

(C)

10.1 Classification (A)

(b) (i1),, (B)
)(iv),
(ii),(C)
(0),
(D) (h)
(ii),(B) (D) (w
(c) (A) (iv), (C)
1. Which of the following is a primary halide?
o(d) (A) (iv), (B) ), (C) (),(D)0)
(b) sec-Butyl iodide (iii),
(a) iso-Propyliodide (D)-()
(d) neo-Hexyl chloride
() tert-Butyl bromide

compounds as primary, 10.2 NomenClaturen

2. Classify the following
secondary and tertiary halides. 6 The IUPAC name of tertiary butyl chloride is

(i) 1-Bromobut-2-ene (a) 2-chloro-2-methylpropane

(ii) 4-Bromopent-2-ene (b) 3-chlorobutane
(iii) 2-Bromo-2-methylpropane o (c) 4-chlorobutane
(ii)-tertiary, (iii)-primary
(a) (i)-secondary,
(d) l, 2-chloro-3-methylpropane
(ii)-primary, (ii)-tertiaryo
(b) ()-secondary,
()-primary, (i)-tertiary,
(iii)-secondary 7. The IUPAC name of(CH),CH–CH,-CH,Bri
(c)

(d) (i)-primary, (i)-secondary,(iii)-tertiary (a) 1-bromopentane

halide? (b) 1-bromo-3-methylbutane

3. Which of the following is not an allylic

(c) 2-methyl-4-bromobutane
(a) 4-Bromopent-2-ene
(d) 2-methyl-3-bromopropane.
(b) 3-Bromo-2-methylbut- 1-ene
(c) 1-Bromobut-2-ene NO,
(d) 4-Bromobut-1 -ene
8. The IUPAC name of the compound
4. Haloalkanes contain halogen atom(s) attached to

CHA
the sp² hybridised carbon atom of an alkyl group.
Identify haloalkane from the following compounds. (a) 1-fluoro-4-methyl-2-nitrobenzene

(i) 2-Bromopentane (b) 4-fluoro-1-methyl-3-nitrobenzene

(i)Vinyl chloride (c) 4-methyl-1-fluoro-2-nitrobenzene

(ii) 2-Chloroacetophenone (d) 2-fluoro-5-methyl-1-nitrobenzene
(iv) Trichloromethane

(a) (i) only

9. Which of the following halides is not correc
o oloboloono according to the name and classification?
Only (i) and (iv)
(b)
(c) Only (i) and (iv) (a) CH,CH,C(CH,),CH,I
(d) Only (i), (ii)and (iii) 1-lodo-2, 2- dimethylbutane, Primary haloakan

(b) (CH,),CHCH(Cl)CH,
Match the column I with column II and mark the
2-Chloro-3-methylbutane, Secondary haloalkan

appropriate choice.

(A)CH,CHCI,
(B) CH,CICH,CI
Column I
) Column
Vinyl halide

Alkylidene
II

halide
(c) CH,C(CI)(C,H,)CH,CH,
2-Chloro-2-ethylbutane,

ne a CH, CI
Secondary haloalkan

= (ii)
(d) CH,CH,-CH-CH-CH,-CH,
(C) CHC| CH, (ii) Alkylenedihalide
(D) CICH,-CH = CH, (iv) Allyl halide
3-Chloro-4-methylhexane,
haloalkane
Secondary
Chemistry
| Haloalkanes and Haloarenes

column I with their

229
Match the isomers given

in
10. s CH,
in column 1I and
names given markthe appropriate
choice. CH-H-CH-CH;+ HCI

ColumnI Column I OH
Br (1) (a) CH,CH– CH-CH,
(A) 2-Bromo-3-methylbutane

CH, CI

(B)r (ii) 2-Bromopentane e (b)

CH,CH–CH-CH,

(C)Br (iii) 1-Bromo-3-methylbutane

CH,
Br (iv)
(D) 1-Bromo-2-methylbutane (c) CH;-C-CH,CH,
CI

(a)

(b)
(A)
(A)
(ii),

(iv),
(B)
(B) -
(i),

(iii), (C)
(C)
(i),
(D)
(iv),

(D) 1)
(i) - (d)

14. Match
CH,CH,CH,CH,CH,CI
the column I with column II and mark the
(c) (A) - (),(B) (),(C) (ii), (D) (iv) appropriate choice.

(d) (A) (),(B) (ii), (C) – (iv), (D) ) Column I

Column II
1. Which of the following is not correctly matched (A) CH,(CH,),OH (i) CH,CH (Br)
NaBr
with IUPAC name?
its
H,SO4, A (CH,),CH,
(a) CHF,CBrCIF: 1-Bromo-l-chloro-1, 2, 2
|(B) (CH).COH Conc. HCI (i) CH,CH,CH,CI
-trifluoroethane room temp.

(b) (CCI,),CCl:2-(Trichloromethyl)-1,1,1,2,3,3, 3 (C) CH,CH(OH) (iii) (CH,);CCI

-heptachloropropane
|(CH,),CH, PBr,
(0) CH,C(p-ClC,H),CH(Br)CH,:
2-Bromo-3,3-bis(4-chlorophenyl) butane D (D) CH,CH,CH,0H(iv) CH,(CH),Br
(a) o-BrCçH,CH(CH,)CH,CH,: (A) –
2-Bromo-1-methylpropylbenzene

nicol Reuct
(a)
(b) (A)
(c) (A)
- (iv),

(iv),

(ii),
(B)
(B)
(B)
(ii),

(ii),

(iv),
(C)
(C) –
(C)
(i),

(ii),

(), (D)
(D)
(D)–)
(i1)

(i)

10.3 Nature of C-X Bond (d) (A) (ii), (B) – (iv), (C) (i), (D) )
12. The main difference in
and a haloarene is
CX bond of a haloalkane 15. Which of the
one monochlorinated
following compounds can
product upon free
yield only
radical

(a) CX
haloarenes.
bond in haloalkanes is shorter than
chlorination?

(a) 2, 2-Dimethylpropane
(b) 2-Methylpropane
(b) in haloalkanes the C attached to halogen in
(c) 2-Methylbutane
C-X bond is sp hybridised while in (d) n-Butane
haloarenes it is sp hybridised.
(c) C-X bond in haloarenes acquires a double
16. Bromination ofmethane in presence of sunlight is a

(a) nucleophilic substitution

bond character due to higher electronegativity
(b) free radical substitution
of X than haloalkanes.
(c) electrophilic substitution
(d) haloalkanes are less reactive than haloarenes
(d) nucleophilic addition.
due to difficulty in C-X cleavage in haloalkanes.

17. The reaction,

Br
104 Methods of Preparation of
CH,=CH-CH, + HBr + CH;-CH-CH, is
Haloalkanes an example of

3. Halogen acids react with alcohols to form alkyl (a) nucleophilic addition
(b) free radical addition
halides. The reaction follows a nucleophilic
substitution mechanism.What will be the major (c) electrophilicaddition

product of the following reaction? (d) electrophilic substitution.

 wtG Objective NCERT at your Fingertiox
230
CH,
CH;
The negative part of the addendum (the molecule
to
18.
be added) adds on to the carbon atomn of the double (c)
bond containing the least number of hydrogen
CH, CHy
atoms. Thisrule is known as
(a) Saytzeff's rule (b) Peroxide rule

() Markovnikov's rule (d) Hoffmann rule. (d)

reactions follows
19. Which of the following 23 Which of the following statements is correct?

Markovnikov's rule? of toluene with

(a) In the substitution
C,H, + Cl,
electrophilic

(a) C,H, + HBr (b) as Lewis acid

Br,, iron (III)bromide acts a

(c) CH, + HBr (d) C,H, + Br;

(b) Inthe reaction of toluene with Cl,/ FeCl,, ortha

Y formed in the
products X and and para isomers are easily separated.
20. Identify the i
(c) Similar reaction with iodine
is reversible
following reaction.

–CH=CH– CH,+ HCIX+ Y nature.

CH,–CH,
of
(a) X= CH,CH,CH,CH,CH,CI, (d) All these.

CH-CH,CH,
Y- CH,CH;H NH,
CI
NaNO, +HCI KI
24. 280 K
+X
(b) X= CH,CH,-CH-CH,CH;
CI X and Yin the reaction are
Y= CH,CH,CH,-CHCH; N,CI

CI
(a)

() X= CH;CH,-CH-CH,CH,
C
N,CI

Y=CH-CH-ÇH-CH,CH, (d)
Ci CI (c)

(d) X =CICH, –CH, CH ==CH–

CH–
CH,
CH,CI
CH=CH-CH,
Y= CH;CH, CH
25. + HBr X,Xin the reaction is
bromide reacts with AgF to give methyl
21. Methyl
fluoride and silver bromide. This reaction is called

(b) Swarts reaction OH

(a) Fittig reaction
Br
(d) Finkelstein reaction. nsti 10 Br
(c) Wurtz reaction

CH-CH,CH, CH,-CH-CH,
10.5 Preparation of Haloarenes
(a) (b)
A compound X with molecular formula, C,H, is
22.
treated with Cl, in presence of FeCl,. Which of
OH
compounds are formed during the
the following
reaction?
O
|oler
CH,-CH-CH,
Br Br

CH--CH,CH,
CH, CH,
(c) (d)
(a)

Br Br
CI

CH, CH,
10.6 Physical Properties
(b) 26. Which of the following molecules has highest

0 dipole moment?
CI (a) CH,CI (b) CH,Cl, (c) CHCI, (d) CC,
 and Haloarenes
|Haloalkanes
oenistry
231
Which of the following compounds has the highest
35. Ethyl alcohol is obtained when ethyl chloride is
boiling
point? boiled with
(b)
(a) CH,CH,CH,CI CH,CH,CH,CH,CI (a) alcoholic KOH (b) aqueous KOH
CH,CH(CH)CH;CI (d) (CH),CCI (c) water
(d) aqueous KMnO
ofthe following is not
Which one correct order 36. Which of the following alkyl halides undergoes

of
boiling points of the alkyl/aryl halides? hydrolysis with aqueous KOH at the fastest rate?
(a) CHCl, > CH,CI, (a) CH,CH,CH,CI (b) CH,CH,Cl
(b) CH;(CH>),Cl> CH,(CH;),CI (c) CH,CH,CH,CH,CI (d) CH,CH,CH(Br)CH,
c) (CH),CCl > (CH,),CHCH,CI 37. Identify the product of the
following reaction.
a) CH;(CH,);Cl> CH,CH,CHCICH, CICH,CH,CH,Br+KCN Product
(a) ClCH,CH,CH,CN
the following compounds in (b) CNCH,CH,Br
Arrange decreasing
29. (c)
orderof their boiling points. CNCH,CH,CH,CN (d) CIÇHCH,CH,Br
(0) CH,Br (ii)CH,CH,Br CN
38. The alkyl halide is
CH,CH,CH,Br (iv) converted into an alcoholby
(i) CH;CH,CH,CH,Br (a) elimination
ia) )> > (ii)> (iv) (b) (iv)> (ii)> (ii) >
(ii) () (b)
o )> (i)> (ii) > (iv) (d) (ii) > (iv) > ()> (i1)
dehydrohalogenation
(c) addition

Which of the following compounds will have (d) substitution.

highest melting point? 39. An alkyl RX reacts

(b) o-Dichlorobenzene
halide, with KCN to give propane
(a) Chlorobenzene nitrile. RX is

. ()
Alkyl

are polar

(a)
m-Dichlorobenzene

halides

because
are immiscible
(d) p-Dichlorobenzene

they react with water to give alcohols

in water though they
40.
(a)
(c)
C,H,Br
C,H;Br
InSN2reactionsthe sequence
bond formation is as follows
(b) C,H,Br
(d) CçH,Br

of bond breaking and

(a) bond breaking is followed by formation

(6) they cannot form hydrogen bonds with water
(b) bond formation is followed by breaking
() C-X bond cannot be broken easily
(c) bond breaking and formation
occur
(a) they are stable compounds and are not reactive.
simultaneously
(d) bond breaking and formation take place

07 Chemical Reactions randomly.

41. Which of the following statements is not correct
32 Cyanide ion acts as an ambident nucleophile.
about Sy2 reactions of alkyl halides?
From which end it acts as a stronger nucleophile in
(a) Nucleophile attacks the carbon from the side
aqueous medium?
opposite to where the leaving group is attached.
(a) It acts as a stronger nucleophile from carbon (b) The bond formation and bond breaking take
end. place in one step.
(b) It acts as a stronger nucleophile from nitrogen (c) The rate of reaction depends upon the
end. concentration of nucleophile.

(c) It depends on the nature of the alkyl halide. (d) Sy2 mechanism is predominant in tertiary

alkyl halides.
(d) It has same strength from both the ends.
42. In the reaction given below,
3. ldentify the products (A)and (B)in the reactions.
CH,CH, CH,CH,
RX +AgCN (A)+ AgX CH, -C--CI +OH HO-C CH,+CI
RX + KCN+ (B) + KX
I

la) (A) RCN, - (B) - RCN H

(A)- RCN, h which of the following statements is correct?
(b) (B) - RNC
(a) The reaction proceeds via S2 mechanism
(c) (4) -RNC, (B) RCN -

hence inversion of configuration takes place.

(d) (A)- RNC, (B)- RNC
To (b)The reaction proceeds via Syl mechanism
4. Butane nitrile can be prepared by heating sleted hence inversion of configuration takes place.

la) propyl alcohol with KCN ii (c) The reaction proceeds via Sy2 mechanism
(b)

(0
butyl

butyl
chloride with
alcohol

propyl chloride with

with KCNle
KCN

KCNego
e
a

(d)
hence their is

The reaction proceeds

no change in

via Syl mechanism

the configuration.

hence there is no change in the configuration.

 232 WetG Objective NCERT at your Fingertips

43. Tertiary alkyl halides are practically inert to 50. Consider the following reaction

:
substitution by S2 mechanism because CH,
(a) the carbocation formed is unstable
C,H,C-Br + H,0H0-C-C,H,+ HBr
(b) there is steric hindrance
(c) there is inductive effect H H
(d) the rate of reaction is
The reaction proceeds with 98% racemisation. The
faster in Sy2 mechanism.
reaction may follow
44. Among the choices of alkyl bromide, the least
(a) Syl mechanism
(b) S2 mechanism
reactive bromide in S2 reaction is
(c) Elmechanism (d) E2 mechanism.
(a) 1-bromopentaneb
(b) 2-bromo-2-methylbutane 51. Which one of the following chlorohydrocarbons
(c) 1-bromo-3-methylbutane readily undergoes solvolysis?

(d) 1-bromo-2-methylbutane. (a) CH,=CHCI (b)

45. Arrange the following compoundsin order of their

reactivity SN2 reaction.p
towards (c) (d) CH,CH,CI
(i) CH,(CH,),CH,Br
(i) (CH,),CHCH,CH,Br 52. Which of the following is the most reactive towards
nucleophilic substitutionreaction?
CH,
(a) ClCH,– CH= CH,ootoni
(ii) CH,CH,-CH-CH,Brsbiledls CH,= CH-
= CH-Cloedorold)
i (b) CI

CH, (c) CH,CH

(iv) CH;-c-CH,Br
(d) C,H;CIool
53. Syl reaction is fastest ini orh sbilas olh
(a) CH,CH,Br (b) CH;
(a) (i) > (ii) > (iiü) > (iv) (b) (ii) > (i)> (iv) > (i) çH-CH,
() (ii) > (i)> (ii) > (iv) (d) (iv) > ()> () > (ii) eaho CH, C1

46. Which ofthe followinghaloalkanes is most reactive?

(a) 1-Chloropropane
(c) CH,C-CI (d) CH,–CH-CI
(b) 1-Bromopropane
(c) 2-Chloropropane (d) 2-Bromopropane CH, CH,
47. Which the following reactions does not take place?
of
enoitaoof looicH,
a (a) CGH,Br + KNO,CH,-0-N=0+KBr 54. Which of the following alkyl halides is hydrolysed
b b) C,H,Br +AgNO,C,HsNO + AgBr by Syl mechanism?
(a) CH,Cl (b) CH,CH,CI
or (c) CH,Br +AgCN C,H,NC + AgBr
S2 C,H,Br + KCN (c) CH,CH,CH,CI (d) (CH,),CCl
(d) CGH,NC + KBr
48, Consider the following bromides 55. Which of the following will give enantiomeric
pair on reaction with water due to presence of
MeBr
saLineniobn BrRRo
Me
Me
Br
Me
asymmetric carbon atom?
C,H
(A) (B) (C)
The correct order of Syl reactivityisal (a) C,H,-Br (b) C,H,-c
(a) A> B> C (b) B>C>A CzHs CH,
2 (c) B> A>Co (d) C> B>A H CH3
49. Which of the following statements regarding the
SNl reaction shown by alkyl halide is not correct?
(c) C,H,(- (d) CH;--Br
(a) The added nucleophile plays no kineticrole in
CH, C,H,
oslg a SNl reaction.ooole 56. Which of the following is most reactive towards
o (b) The Syl reaction involves the inversion of
aqueous NaOH?
Siy configuration of the optically active substrate.
(a) CçHsCl (b) CçH,CH,CI
(c) The Syl reaction on the chiral starting material () CçH,Br (d) BrCçH,Br
ends up with racemisation of the product.
(d) The more stable the carbocation intermediate 57. In the following pairs of halogen
compounds, which
the faster the Syl reaction. compound undergoes faster Syl reaction?
 |Haloallanes and Haloarenes
233

(a) ()and (i) only (b)(), ()and (ii)only

(c) ()and (ii)only (d) ()only.
64. Ethylene dichloride and ethylidene chloride are
and
isomeric compounds.The false statement about
these isomers is that they
(a) are both hydrolysed to the same
product
(b) contain the same
percentage of chlorine
(c) are position
isomers
(d) react with alcoholic potash
and give the same
product.

65. The major product formed in the following reaction is

CH,
CH,0
(i1) CH,C-CH,Br cH,OH
H
58. Which of the following haloalkanes reacts with

agueous KOH most easily? GH,

(a)
(a) 1-Bromobutane CH,Ç-CH,0CH,
(b) 2-Bromobutane H
() 2-Bromo-2-methylpropane
(b)
(d)2-Chlorobutane CH,-CH-CH,CH,
s Which alkyl halide exhibits complete racemisation 0CH,
in Syl reaction?
(a) (CH,),CHCI (b) CH,CH,CH,CI
(c)
(c) CH;CH,CI (d) CçHsCH,Cl CH,-C=CH,
60. The order of reactivity of various alkyl halides CHs
towards nucdeophilic substitution follows the order
(a) CH,-e-CH, ola
(a) R-I>R- Br> RCI>RFO) oiingoladorbedob
OCH,
(b) R- Br > R-I
R-F>R-Cl > 66. Which of the following reactions
() R-Cl>R-Br RI>R-F >
will give the major

R-Br RI>R–Cl>RFoe minor products?

and
(d) >
alc. KOH
CH;-CH,-CH-CH, heat
6L. Alkyl halides are formed when thionyl chloride
and Br
are refluxed in presence of pyridine.
The order of reactivity (3° > 2° > 1°) is due to +I CH,-CH=CH-CH, +CH-CH,-CH=CH,
(A) (B)
effect of the alkyl groupwhich the polarity

of C-X bond. (a) (A)is major product and (B) is minor product.
(a) acids, decreases (b)alcohols, increases (b) (A)is minor product and (B) is major product.
to (c) Both (A)and (B) are major products.
(c) aldehydes, changes (d) ketones, decreases
3 (d) only (B) is formed and (A)is not formed.
62. 2-Bromo-3,3-dimethylbutane on reaction with
67. The products (A)and (B) are respectively
aqueous KOH yields X as the major product. X is GH,ONa,
(i) CH-CH-CH-CH,- 4)
(a) 2, 3,3-trimethylpropan-1-olo
(b) 2,2-dimethylbutan-3-ol
Br CH
(c) 2,3-dimethylbutan-2-ol
(d) 2,2-dimethylpropan -2-ol HBr
(i) CH,=C-CH,CH; Feroxide (B)
B. Among the isomers of C&HCl, the one which is

chiral is CH,
) 2,2-Dimethy-1-chloropropane 0 (a) CH,CH,-H-CH, CH,(CH),CH,
() 2-Chloropentane
(ii) 2-Methyl-2-chlorobutane
(b) CH,CH,–çCH): (H-çH-CH CH,
(iv) OC,H, Br CH,
3-Chloropentane
 WtG Objective NCERT
your
234 Fingentigs
Which of the following products

as
73. shownby
() CH,CH-CH-CH,CHy dehydrohalogenation
of alkyl halides
with
the
in ethanol is correctly marked sodium
ONa ethoxide as
major
product?
BrCH,-C-CH,CH, Br CH,ONa
6) CH,OH
Br cH,
(Minor)
(Major)
(d) CH,CH,CH,CH;CH, CH,-ÇH-CH;CH; Br
Br CH,ONa
(i) CH,-CCH,CH, CzH;OH
68. A mixture of 1 -chloropropane and 2-chloropropane
when treated with alcoholic KOH gives

(a) prop-l-ene

(b) prop-2-ene
a mixture of prop-1-eneand prop-2-ene
|
CH,=C-CH,CH, +
CH,
(Minor)
+CH;-CFCHCH,
CH,
(c) (Major)

(d) propanol.
reaction and identify
X
69. Consider the following C,H,ONa

and Y. (ii) CH;-C-CH,CH; CzH;OH

CH,CH,CH,I c KOH,XBr,y CH,Br

Y
X
(a) CHCH = CH, CH,-CH-CH,Br
CH–C-C=CH--CH, +o
Br
CH,CH,CH,Br
1otes
CH,
shi CH,CH,
(b) CH,CH,CH,OH (Major)

() CH;CH-CH; CH;-CH-CH, CH IC-CH,-CH,

Br CH,
OH (Minor)

(d) CHCH =CH, CH,CH,CH,Br

(a) Only (i) and (ii) (b) Only (i) and (ii)
An halide with molecular formula,
CH3Br (d)
70. alkyl
(c) Only (ii) and (iii) only (ii).

on
dehydrohalogenation gives two isomeric
formula, CçH2: 74. Match the reactions given incolumn with the tyne I

alkenes and Y X
with molecular
X and Y gave four of reaction mentioned in column II and mark the
On reductive ozonolysis
appropriate choice.
compounds CH,COCH, CH,CHO, CH,CH,CHO
and (CH),CHCH0. The alkyl halide is Column I Column II

(a) 4-bromo-2-methylpentane (A) CH,-CH-CH- CH, ()B-elimination

(b) 3-bromo-2-methylpentane Br CH,
(c) 2-bromo-2,3-dimethylbutane
+C,H,ONa
(d) 2,2-dimethyl-1-bromobutane.
OC,Hs
71. Arrange the following alkyl halides in order of
CH,CH,-C-CH,
dehydrohal ogenation; C,Hl, C,H,Cl, C,H,Br,
CzH,F CH,
(a) CH,F > CzH,Cl> C,H,Br > CzHI
(b) C,H,I > C,H,Br > CzH,Cl> C,H,F
(B)
CH,CH,Br
AgOH
(ii) Sl nucleophilic

substitution

(c) C,H,I > C,H,Cl > C,H,Br >C,H;F CH,CH,OH

(d) CzH,F> CzH;I > CçH,Br > C,H,CI (C) CH,CH= CH, + HBr (i) S2 nucleophili

Peroxide substitution
72. 2-Chloro-2-methylpropane on reaction with
alc. KOH gives X as the product. X is CH,CH,CH,Br
(a) but-2-ene
(D)CHj–CH,Br + (iv) Kharasch effec

(b) 2-methylbut-1 -ene alc. KOH

() 2-methylprop-1-ene
(a) 2-methylbutan-2-ol.
CH, = CH,
 Halbalkanes and Haloarenes
235
(a) (A) (iv), )>(0),(C)(), (D)
(B)
())
(b) (A)- (i), (B)
(D)) (),(C)((v), (e) (CH),CBr+KOH hanol,

(e) (A)- ().(B) i), (C) (iv), (D) () CHy

(A)(ii), (B) - ().(C)
(d) (i),(D) (v)
chloride produces
CH-CH, +H,0+ KBr
An alkyl a single alkene on
with sodium ethoxide and (d) CH,CH,CHCH, + HBr Peroxide.
reaction ethanol. The
alkene further undergoes hydrogenation to yield
2-methylbutane.Identifythe alkyl chloride amongst
CH,CH,-CH--CH,
Br
the following compounds.

(a) CICH,CH(CH,)CH,CH, 81. CH;-CH-CH, Ale. KOH xHB Peroxide

Y
Nal
Acetone
(b) CICH,CH,CH,CH,
ic)CICH,CH(CH)CH,CH, In the given reaction
what will be the final product?
a) CH,C(C)(CH,)CH,CH, (a) CH,CH,CH,I
(b)
CH,CHICH,I
of (c) CH,CH,CH,CH,CH, (d) CH,CH,CHI,
76. RReaction trans-2-phenyl-1-bromocyclopentane
on reaction
with alcoholic
producesKOH 82. Grignard reagent,a very
useful starting compound
(a) 4-phenylcyclopentene for a numberof organic reactions can be preparedby
(6) 2-phenylcyclopentene (a) reaction of alkyl halides with a solution of
(c) l-phenylcyclopentene magnesium hydroxide
(d) 3-phenylcyclopentene. (b)reaction of
alkyl halides
with dry magnesium
powder
presence of dry ether
in
7. ldentify (Z) in the following reaction series,
(c) reaction of MgCl,with ether and

CGH,I
Alcoholic
KOH
,(Xx) "2y ()KCN, (Z) (d) reaction of alkyl
alcohol

halide with magnesium in

(a) CH,CH, CN (b) |

CH,-CH,
CN CN
83. The order of
presence of alcohol.

reactivities

formation of Grignard reagent is

of methyl halides in the

(a) CH,I > CH,Br > CH,CI

CH,- CH,
Br CN
(d) |
CH=CH
Br CN
(b)

(c)
(d)
CH,Cl> CH,Br > CH,I
CH,Br > CH,CI > CH,I
CH,Br > CH,I> CH,CI

78. The ease of dehydrohalogenation of alkyl halide 84. Identify the products X and Y in the given reaction,

alcoholic KOH is D,0

with
CH,-CH-CH, + Mg Dy ether x

(a) 3° < 2° < 1° (b) 3° > 2° > 1°h

(c) 3° < 2° > 1°(d) 3° > 2° < 1o
Br

79. Elimination of bromine from 2-bromobutane (a) X=CH,-CH-CH,Mg, Y =CH,CH,CH,OH

results in the formation of Br

(a) equimolar mixture of 1 and 2-butene

predominantly 2-butene
(b) X= CH, CH-CH, Y= CH,-ÇH-CH,
(b)

1-butene MgBr
(c) predominantly
predominantly 2-butyne.
X= CH;-CH-CH,Y= CH,-ÇH- CH,
(d)
(c)
80. Which of the following products does not match OD
correctly with the reaction?

(a) CH,CH=C(CH,b + HBr CH, (d) X= CH,-ÇH-CH,Mg, Y = CH,-CH-CH,

CH,-CH,-C-Br Br
OH
CH,
with metallic sodium in dry
85. Alkyl halides react
(D) CH,CH-CH,CH,
+NaOH Water
ether producing
Br (a) alkanes with same number of carbon atoms
ofcarbon atoms
(b) alkanes with double the number
ES CH,-CH-CH,CH, + NaBr + H,0 (c) alkenes with triple the number of carbon
atoms
atoms.
OH (d) alkenes with same number of carbon
 MtGbjective NCERT at your
Fingerti
236
on treatment with
with 87. Chlorobenzene sodiumin
86. Ontreating a mixture of two alkyl halides
dry
diphenyl. The
name of the
was ether gives reaction is
sodium metal in dry ether, 2-methylpropane reaction
(a) Fittig
obtained. The alkyl halides are
(b) Wurtz-Fittig reaction
(a) 2-chloropropane and chloromethane
reaction
(b) 2-chloropropane and chloroethane (c) Sandmeyer
reaction.
(c) chloromethane and chloroethane (d) Gattermann
and 1-chloropropane.
(d) chloromethane
compound ().(n) reacts with
HBr to give
(X)reacts with alc. KOH to give

Primary halide, C,H,Br with Na metal it gives compounds (P).(X),(n,

88. alkyl
When(X)reacts (Z)
is anisomer of (X).
Compound(Z) which

and (P) are

p

Br

CH,8
CH,-C-CH,
(a) CH,CH-CH,Br CHy
CH,
nsiaagoCH,
CH;
CHi0
CH,CH =CHCH, CH;- çHCH,CH,
(b) CH,CH,CH,CH,Br

)
Br

CH,CH-CH,CH;eh
CH,CH = CHCH, CH,CH,CH,CH,Br C,H4

Br

(d) CH,-CH-CH,Br CH,CH =CHCH; CH, ÇHCH,CH;oCcHj:

B

CH, odoola tooe

CI
reaction with sodium
89. Tertiary butyl bromide on O,N. NO,
to otierm
givesngino
methoxide mainly (ii)
(a) tert-butyl ethyl ether (b) 2-methylpropene
(d) iso-propyl alcohol.
(c) propene NO,
90. Aryl

O due
halides

substitution

todt
are less reactive
reactions

(a) formation ofa less

as compared

stable
towards nucleophilic

carbonium
to alkyl

ion
halides

in aryl
s61 (b)
(a)

(c)
(ii) >

(i)
i)>
>
(i)> (1)
(ü) >()doriob
(ii) > (ii)
t ok
halides (d) ()> (ii) > (1)
in aryl halides
(b) resonance stabilisation
92. Match the column I with column IIand mark the

HC(c) presence of double bonds in alkyl halides

i appropriate choice. tiaod
(d) inductive effect in aryl halides.
Column I Column II

91. Chlorobenzene can be converted into phenol by

(A) CI (i) CH,CH,CH,Br
heating in aqueous sodium hydroxide solution
at a temperature of 623 K and a pressure of 300 Cl;

atm. However the rate of reaction can be increased abong

by presence of certain groups in benzene ring.
Na
ether
What will be the order of reactivity of following
(B) (ii) OH
compounds towards the above substitution reaction?
CI OH b
CH,-C-Br
NaOH,
623 K. 300 atm
CH,
OKOH NO,
CI CI C,H,OH
CH,

s() a (i) 8CH;-C HBr

Peroxide

NO, NO,s b
CH,
 Chemistry

(C)
|Haloalkanes

CI
and Haloarenes

(iii)
237

conc. HNO, 10.8 Polyhalogen Compounds

conc. H,SO, 95. Chloroform kept
is in dark coloured bottles because
(a) it reacts with clear glass
(b) it undergoes chlorination in
NaOH transparent glass
bottles

l49s 832(d)
dil. H

(c) itisoxidised
to poisonousgas,
9 phosgene in sunlight
NO, it
burning when exposed to
starts
sunlight.
(iv) 96. Triiodomethane
(D) has antiseptic property because
of
(a) liberation of
CH,-CH-CH, CH-CH iodoform
KOH (b) liberation of free
iodine
C,H,OH (c) formation of
CH,-Br phosgene gas
CH;CH=CH, (d) none of these.
HBr
Peroxide 97. The fire extinguisher'pyrene'
contains
(a) carbon dioxide
(a) (A) (iv), (B) (ii), (C) ),(D) (ii)
(c) carbon tetrachloride
(b) carbon disulphide
(d) chloroform.
(b) (A)(iii),(B) (iv), (C) (ii), (D) ) 98. An organic halogen compound which is used as

(c) (A) (ii), (B) (),(C) (ii),(D) (iv) refrigerant in refrigerators and air conditionersis
(a) (A) (i), (B) (ii), (C) (iv), (D) (ii) (a) BHC (b)CCI, (c) freon (d) CHCI,
83. The end product (Q)in the following sequence of 99. Which one is correct? D

reactionsis (a) Freon-14 is CF4, Freon-13 is CF,CI, Freon-12

CFeCsP Na/ethersoir is CF,Cl, and Freon-1l is CFCI,.

(b) Freons are chlorofluorocarbons.
CH, (c) Freons are used as refrigerants.

(a) (b) (d) All the above.

OH 100. Match the column I with column IIand mark the
(d)
() appropriate choice.
Column I Column II

94. Which of the following reactions is not correctly Carbon

(A) (i) Paint remover
matched? tetrachloride
dry ether
(a) 2C,H,Br + 2Na + C,H0+ 2NaBr; Methylene Refrigerators and air

Wurtz reaction (B) chloride

(ii)
conditioners

(b) CH,Br +AgF CH,F + AgBr; (C) DDT (iii) Fire-extinguisher

Etard reaction Non-biodegradable

(D) Freons (iv)
insecticide
dry ether
(c) CH,Br + 2Na +BrC,Hs (a) (A) (ii), (B) (ii), (C) (),(D) (iv)

CçH,C,H, + 2NaBr; Wurtz-Fittig

reaction (D) (i)
(A) (iv), (B) (iii), (C) (ii),
(b)
(A)- (B) (ii), (C) (ii), (D) (iv)

+CçH;CoH,+2NaBr; (c)
dry ether (i),
(d) 2C,H,Br+2Na (B) (),(C) (iv), (D) (ii)

Fittig reaction (d) (A) (iii),

is
Ifyour score are on your
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 NCERT
EXemplarProblems MCQs of "NCERT Exemplar
Problems' Book

This section contains

5. Which ofthe following is halogen

exchange reaction?
1. The order of reactivity of following alcohols with (a) RX Nal + RI + NaX
halogen acids is
CH,OH (b)=c HX
(1) CH,CH HX
(I) CH;CH-CH-OH
(c) R-OH + HX RX+ H.0
CH, CH,
CH, Fe
Sark
CH,
(IDCH;CH--OH
CH,
(I)> (T) X
> (II) > (III) (b) (III)>
(a) (I)
(d) (I) > (III) > (I)
(c) (1)> () > (III)
6. Which reagent will you use for the following reaction?
will yield the
2. Which of the following alcohols CH,CH,CH,CH, CH,CH,CH,CH,CI+
on reaction with
chloride
corresponding alkyl CH,CH,CHCICH,
temperature?
concentrated HCl at room (a) Cl,/UV light
(a) CH,CH,-CH-OH (b) NaCl + H,SO4
(b) CH,CH,- ÇH-OH (c) Cl, gas in dark
(d) Cl, gas in the presence of iron in dark.
H,
(c) CH,CH,- CH-CH,OH 7. Arrange the following compounds in the increasing

order of their densities.

CH, C

CH,
(II)
(à) CH,CH-OH (I)

CH, C Br
3. Identify the compound 'Yin the following reaction.

NH, N,CI (II1)

NaNO, +HCI CuChy Y+N2 CI
273-278 K

(a) (I) < (II) < (III) < (IV)

CI
(b) ()< (III) < (IV)<(I)
(a) (b)
(c) (IV) < (III) < (II) < (1)

C1 (d) (I) < (IV) < (III)< ()

8. Arrange the following compounds in increasing

(c) (d)
order of their boiling points.

CI CI CH3
(I) (II) CH,CH,CH,CH,Br
4. Toluene reacts with a halogen in the presence CH-CH,Br
CH;
of iron (III) chloride giving ortho and para halo CH,
compounds.The reaction is
(I) H;C--C-CH,
(a) electrophilic elimination reaction
substitution reaction Br
(b) electrophilic
(c) free radical addition reaction (a) (11) < ()< (III) (b) ()< (I1) < (III)

(c) () < (I) < (I1) (II)< (I1)< ()

(d) nucleophilic substitution reaction. (d)
 Haloalkanes and Haloarenes
Chemistry 239
which of the following moleculescarbon atom
In

marked with asterisk () is

asymmetric? CH,-CH=CH,
H D
(a)

Br
() C
Br CH,-CH;-CH,-CI
(b)

()HO C,Hs
(IV) HCH,
C,Hs
() (),(I),(II), (IV) (b) (),(),(ID CH-CH,-CH,
CI
(c) (1), (II), (IV) (d) (1), (II), (IV) (c)
(d)
Which the following structuresis
of
10. enantiomeric
with the molecule given below? () 16. A primary alkyl halide would prefer toundergo
H
(a) Syl reaction
(b) Sy2 reaction
(c) a-elimination
H,C, (d) racemisation
Br
17. Which of the following alkyl
halides will undergo
(1)
SNl reaction most readily?

MC,HsH
6n (b) Br
C
(a) (CH,),C-F
(c) (CH;),C--Br
(b)
(d)
(CH,),C-CI
(CH,),C-I
H,C 18. Which the correct
(a)
Br
is
IUPACname for
C,Hs
H CH,-CH-CH,-Br ?
Br
nstdocion - oct Br

dol C,H,
(d) (a)
(c) H;C H;Cz 1-Bromo-2-ethylpropane
CzHsastoboCH3 (b) 1-Bromo-2-ethyl-2-methylethane
(c) 1-Bromo-2-methylbutane
11. Which of the following is an example of
vic-dihalide? (d) 2-Methyl-1-bromobutane

(a) Dichloromethane 19. What should be the correct IUPAC name for
(b) 1,2-Dichloroethanei SsTUl b)
diethylbromomethane?
(c) Ethylidene chloride (a) 1-Bromo-1,1-diethylmethane
(d) chloridei Jooo0
Allyl
itdoidh (b) 3-Bromopentane
12. The position of the compound
Br in (c) 1-Bromo-1-ethylpropane
CH,CH=CHC(Br) (CH,), can be classified (d) 1-Bromopentane
as skasdono 20. The reaction toluenewith chlorine in the presence
arylon (
of
(a) allyldoimun8 I (b)
of iron and in the absence of light yields
(c) vinyl bngog (d) secondary

13. Chlorobenzene is formed by reaction of chlorine CH,CI CH,

(a) (b)
with benzene in the presence of AlCI. Which of

the following species attacks the benzene ring in

this reaction?seiion
(d) mixture of (b) and (c)
(a) Cle (b) CI (c) AlCI, (d) [AlCIJ
14. Ethylidene chloride is a/an 21.Chloromethane on treatment with excess of
(a) vic-dihalide (b) gem-dihalide
ammonia yields mainly
(c) allylic halide (d) vinylic halide
(a) N-dimethylmethanamine (CH-N )
15. What is A' in the following reaction?
N,
CH,
CH,-CH=CH, (b) N-methylmethanamine (CH;-NH–CH;)

+ HCI (c) methanamine (CH,NH,)

(d) mixture containing all these in equal proportion.
 wtG Objective NCERT at
yous
Fingetis

240

22. Molecules whose mirror image

is non
(I1)
over them are known as chiral.
27. ()
superimposable is chiral in CH,
Which of the following
molecules
() (I)< <()
< () (b) ()
< (III) <(I)
(I) <()
nature? (a) (d) (I1)<(II)<()
(b) 1-Bromobutane (c)
(a) 2-Bromobutane
(d) 2-Bromopropan-2-ol O,N
(C) 2-Bromopropane
with aqueous sodium () (1)
of CHCH,Br
23. Reaction 28. ()
hydroxide follows

(a) Syl mechanismn NO; NO,

(b)Sy2 mechanism upon the
<(I) <(1) (b)(II) < (III)< (I)
the above two
depending (a) (III)
(c) Any of (d) ()< (II)< (III)
of reaction (c) ()< (II) < (II)
temperature C1 C
8a) Saytzeff rule
in the molecule
C

CH,
atoms present
24. Which of thecarbon (II)
(III)

are asymmetric? 29. (I)

given below
OHH CH, CH,

< (II) < (III) (b) (I1) < (I) < (I)
H OH (a) (1)
< ()
(II) < (I) <()
(d) (I) < (III)
(c)
(a) (), (ii), (i),
(iv)

Which is the correct increasing order of boiling

30.
b) (),(ii) compounds?
() 0. (iv) points of the following
1-Chlorobutane,Butane
(d) ).(ü), (ii) 1-lodobutane, 1-Bromobutane,
will give < 1-Chlorobutane < 1-Bromobutane
25. Which of the following compounds (a) Butane
substitution by <1-lodobutane
racemic mixture on nucleophilic

)
OH ion?

CH- CH-Br
CzHs
()CHy CH,
C,Hs
(b) 1-lodobutane<1-Bromobutane
<1-Chlorobutane< Butane
(c) Butane < 1-Iodobutane < 1-Bromobutane

(d) Butane < 1-Chlorobutane <

1-Iodobutane
< 1-Chlorobutane

()CHÇHCH,Br <1-Bromobutane
C,Hs
31. Which is the correct increasing order of boiling
(a) () (b) (),(II), (III)

(d) (1), (II) bapoints of the following compounds?

(c) (I), (II)
bar 1-Bromoethane, 1-Bromopropane,1-Bromobutane,
Direction :In the questions 26 to 29 arrange the Bromobenzene
compounds in increasing order of rate of reaction (a) Bromobenzene < 1-Bromobutane
towards nucleophilic substitution. sbi< -Bromopropane < 1-Bromoethane
CI C C n (b) Bromobenzene < 1-Bromoethane
NO, Dl<1-Bromopropane < 1-Bromobutane
26. (I) () (III)|
a c) 1-Bromopropane < 1-Bromobutane
NO <1-Bromoethane < Bromobenzene
oit(a) ()< (I) < (III) (b) (III) (I)
< < () (d) 1-Bromoethane < 1-Bromopropane
(c) () (II) <
< (II) (d) (m) < ()< (II) < 1-Bromobutane < Bromobenzene
 Exam Scorer
|This section is
exclusively desianed for NEETL JEE CUET Board exams.

:A8RCOrner b in polar protic solvents (like water, alcohol, acetic

the following acid,etc.)
pirections questions, a statement
is followed by a of Reason :CçH,CH(CGH,) Br is less reactive than
assertion statement of reason.
as : Mark the CçH,CH(CH)Br in Syl reactions.
correct choice
f both
assertion and reason are 10. Assertion:S2 reactionproceeds with racemisation
true and reason
the correct explanation of
assertion.
is
while Sl
reaction proceeds with complete
f both stereochemical inversion.
assertion and reason are
true but reason
not the correct explanation of assertion.
is
Reason S2
step reaction.
: is two steps reaction while Syl is one
If assertion is true but reason is false.
If both assertion and reason are false.
11. Assertion :CH-CH-CH,CH, on reaction with
Assertion: CH, CH-CH,–X is an example of alcoholic KOH
gives CH,CH=CHCH,
allyl halides. as a result
of
Reason :These are the compounds in which the dehydrohalogenation.
Reason: Elimination reaction takes
atom is bonded to an sp hybridised carbon
halogen place in
accordance with Markovnikov's
rule.
atom.
12. Assertion :Aryl halides are highly reactive towards
2.
Assertion :Common name of 1,1-dichloroethane nucleophilicsubstitution reactions.
isethylidene chloride. Reason:In case of haloarenes, halogen
Reason :Ethylidene chloride atom is
is a gem-dihalide. attached to sp hybridised carbon atom.
3 Assertion : Aryl halides cannot be prepared 13. Assertion :Replacement of
-Cl group by -OH in
by replacement of hydroxyl group of phenol by chlorobenzene is easier if nitro group is present in
halogen atom. the ring.

Reason :Phenols react with halogen acids violently. Reason :Nitro group leads to strengthening of the
C-Cl bond in chlorobenzene.
4. Assertion :On free radical monochlorination of
14. Assertion :Electrophilic substitution
(CH,),CHCH,CH, four monochloro structural reactions in
haloarenes occur slowly and require more drastic
isomers are possible.o
conditions as compared to those in benzene.
Reason:In (CH;),CHCH,CH,there are four different
Reason :Halogens are ortho and para-directors.
types ofhydrogen atoms.
15. Assertion :Chloroform is stored in dark coloured
5. Assertion : Melting points of isomeric dihalo bottles.
benzenes are nearly thesame.
Reason: Chronic chloroform exposure may cause
Reason :Isomeric dihalobenzenes have different
damage to the liver and kidneys.
molecular masses.

6. Assertion :The boiling point of the compounds

increases in the order:ops 91lib Case Based Questions
<1-Chloropropane < 1-Chlorobutane. the following
Isopropylchloride Read the given passages and answer
Reason :Boiling point dependsupon the molecular questions.
mass and surface area.
Thereplacement of one or more hydrogen atomsin
7. Assertion : Haloalkanes react with KCN to form in the formation
hydrocarbon with halogen results

alkyl cyanides as main product while with AgCN of a halogen derivative of the hydrocarbon.
In
form isocyanide as the main product. the product is
case the hydrocarbon is aliphatic,

Reason :KCN and AgCN, both are ionic compounds. and in case of aromatic hydrocarbons,
haloalkane

8. Assertion of reactivity of alkyl halides

:The order the product is haloarene.

towards Syl reaction is tertiary halide>

secondary In the system, aliphatic halogen derivatives
common
are named halides. Thewords n-, sec-, tert-,
as alkyl
halide > primary halide.
Reason: The reaction follows carbocation mechanism. boir iso- and ne0- are usually used in writing the

9. Assertion : Syl reactions are generally carried out

common names. In IUPAC system, they are
 wtG Objective NCERT at
your F
242 These reactions Fingertigs
to form alkenes.
are
alkanes because the
considered as derivatives of corresponding B-eliminations hydrogen atom
called

and are named as haloalkanes. the haloalkaneiis present

B-position removed.

of
at

Haloarenes are named

parent aromatic compound.

at 1, 2-; 1,3- and

respectively.
by prefixing the halogen

and its position, if necessary,

names, the relative positions

1, 4-

by prefixes ortho(o-),
to the name of the
In writing the common
of the substituents
positions
meta(m-)
are indicated
and para(p-) Haloalkane

CH-CH-Br + KOH(alc.)
Bromoethane
. OHaE)

+H,C=
c=c(+H0.x
Alkene

Ethene
CH,+ KBr
+H,0
the given compound
is

The IUPAC name of

1. In case, the haloalkane can eliminate
CH, in two hydrogen
C- Br is halide
which
different ways, the preferred
alkene
isthe one is maximum alkylated, i
CH, number of alkylgroups
i.e.,

CH, –CH,Br more which

carries
attached
l carbon
ot
to
the
doubly bonded atoms. This
(a) 1,3-dibromo-3-methylbutanego2 generalisation is
rule.
(b) 3-methyl-1,2-dibromobutane
known as Saytzeff's

(c) 3-methyl-1,3-dibromopropane
(d) None of these. HOXilodela 6. Br
H-CH,Br alc.

NaNH2
KOH A CH,CH,C
NaNH,

given compound is
2. The IUPAC name of the
rii A and B are
H 93eos
HiBrnoiseA
CH,ilitigoabt
oess oi
(a)
4-Orc,, B= yCH;CH,

snoeagH C=CH
3-bromo-2-methylbut-1-enel
2l (a)

(b) 4-bromo-3-methylpent-2-ene
obsts Cac-CH,-H

c) l-bromo-2-methylbut-2-eneobogore
dooldb CH,CH,C=CH
nt(d) None of these.
()
3. The structure of 1-bromo-4-sec-butyl-2-methyl
sili benzene is sslorab CECH Lc=C-CH,
Br CH, o(d) ,- B

Br
CH CH,CH, (b)
7. Identify the set of reagent/reaction conditions 'X

notosnL
nsrand Y
in the following set of transformations:
bhsotho H,C CH-CH, CH,
CH,
bolahbgtbetote al soscosolDaoioA CH,-CH,-CH, Br Product CH,-CH-CH,
Br
Br Br

CH, (a) X =dilute aqueousNaOH, 20°C;

(c) Y= HBr/acetic acid, 20°C
H,C-CH
(b) X= concentrated alcoholic NaOH, 80°C;
anomoD9 CH-H–CH,CH,
bnuog
(c)
Y= HBr/acetic
X= dilute
acid, 20°C
aqueousNaOH, 20°C;
4. Iso-butyl chloride in IUPACis named asit bsal do Y= Br,/CHCI, 0°C
(a) 1-chloro-2-methylbutane si (d) X= concentrated alcoholic NaOH,80°C;
(b) 1-chloro-2-methylpropane Y= Br,/CHCl,, 0°C.
(c) 2-chlorobutane 8.
In the following sequence of reactions,
(d)2-chloro-2-methylpropane.0aonhe
5. Which of the following is not an allylic halide? CH,CH,CH,Br
KOH (alc.)
(A)
HBr
+ (B)

(a) 4-bromopent-2-ene
KOH (a4)
(b) 3-bromo-2-methylbut-1-ene
(c) 1-bromobut-2-ene The product (C) isoooonk
(d) 4-bromobut-l-ene (a) propenea(b) propyne
(c) propan-1-ol (d) propan-2-ol
When haloalkanes with B-hydrogen atoms are heated 9.
with alcoholic
KOH, they undergo Thecompound (A) CaH,Cl on dehydrochlorination
dehydrogenation SuO gives 516otoe h
Chemistry
|
| Haloalkanes

CH-C=CH-CHs
and Haloarenes

243

CH, I.
III.
RX+ YR-
RX*+YR- Y+X
Y +X
compound (A)could be
The
IV. RX+YR- Y +X
(a)
CH;-CHCl-CH,CH,-CH,-CH.In which there is large increase and
reactions
(b) large decrease in rate of reaction
CH;-CH-CHCI-CH,CH,-CH, increase in polarity of the solvent?
respectively with
(c) CHs-CH-CH-CHs (a) II and III
(b) Iland IV
CH, CI (c) I and IV
(d) IV and I
(d) None of these.
2. 36.4 g of
10. The (X)of the reaction
major product 1,1,2,2-tetrachloropropanewas heated
with zinc dust and the
product was bubbled
(CH),C-Br KOH > X+ KBr + H,0
+ through ammoniacal
AgNO,. What is the weight
is
of precipitate obtained?
(a) 2-methylpropene (b) but-2-ene (a) 30.0 g
ic) 2-methyl-but-2-ene (d) but-l-ene. (b) 29.4 g
(c) 28.0 g
(d) 25.7g
3. CRH,CI,(A) Aq. NaOH Mild
Numerical Value TypeQuestions L/NaOH
(B) reduction
(C)

Answer the following questions as integer or

iodoform + acid salt (D)
numerical In the given sequence of
value. the structure of
reaction, what would be

bCH, Br,CCl, (a) PhCOCH,

((A)?

(b)
H
PhCH(OH)CH,
1. CH, OH -HoE] 5 such
(c) PhCOONa (d) PhC(C),CH
products 4. Cyclobutyl bromide on treatment
with magnesium
are possible in dryether formsan
organometallic compound (A).
The number of possible structures of Fis a The organometallic compound reacts
with ethanal
o to give an alcohol (B) after mild
2. Among the given compounds, the number of acidification.

compounds that
ir Prolonged treatment of alcohol (B) with an
willnot give white precipitate
with AgNO, is
equivalent amountof HBr gives (C).What will be
the product 'C?
(1) CH,CH,Br (i) CH3CH,CI (a)
Cl 1-Chloro-1-ethylcyclopentane
CH,CI (b) 1-Bromo-1-methylcyclopentane
(c)
3-Bromo-2-methylcyclopentane
(ii) CH,=CH - CI (iv) (v) (d) None of these.

(vi) CHI, 5. Bottles containing CçH,I and CçH,CH,I lost their

3. The number of possible enantiomeric pairs that original labels. They were labelled A and B for
can be produced during monochlorinationof A and B were separately taken in test tubes
testing.
and boiled with NaOH solution. The end solution
2-methylbutane is
in each tube was made acidic with dilute HNO,
Among the following alkyl halides,the total number
4.
and some AgNO, solution added. Solution B gave
which react with SN1 mechanism is
a yellow precipitate. Which one of the following
CH,Br, CH,CH,Br, CH,CH,CH,1, (CH),C- Br, statements is true for the experiment?
BrCH,CH=CH,, C,H,CH,Br, CçH,-CHBr-CH, (a) Addition of HNO, was unnecessary.
CH,CH=CHCH,CIp eiviosbd sl (b) A was CçH,l
Brl stgaosaTol (c) A was CçH;CH,I

5.
HCH, CH,
H,
Catalyst
P
6
(d) Aand B can't be predicted

0.0852 g of an organic halide (A) when

by

dissolved in
this experiment.

mixture
chiral centres are present product P? 2.0 g of camphor, the melting point of the
How many in

was found to be 167°C. Compound (A) when heated

with sodium gives gas (B).280 mlL of gas (B) at
a

ThinkingCorner STP weighs 0.375 g. What would be A' in the whole

Ihis section includes Olympiads & Higher Order Thinking process? (K,for camphor =40, m.pt. of camphor
Skills questions.
= 179°C.)
(a) C,H,Br (b) CH,I
1. Consider the following S2 reactions (d) C,H,Br
I. RX+ yR-Y+X (c) (CH,),CHI
 This section includes previous years' PMTS and JEE Main questions based on
NCERT Core
content

1. Major product 'B of thefollowingreaction 6. The major product in the

sequence is reaction

CH;-CCH-CH, A H (major product) CH,-¢+

CH,

KO--CH,
CH,

CH, CH,
H Br Br CH,
(a) -butyl ethyl ether (b)
CH-CH-CH () CH-cH-CH,
2,2-

(a) (c) 2-methylpent-1-ene (d) -himethylbutane

H
CH, 2-methylprop-1.- -ene

Br OH Br (JEE
Main)

o0CH--CH-CH, CH,
(a) CH-CH-CH,
Hs
7. The correct sequence
bond is
B(a) CH-Cl>
of bond
enthalpy of
'C-x
(JEE Main)
(b)
CH,-F> CH;-Br > CH,
2. Which of the following is suitable to synthesize
CH-F<CH,-Cl< CH-Br < CH
(c) CH;-F> CH,-Cl>
chlorobenzene? CH, -Br > CH
(a) Benzene, Cl, anhydrous AlCl; (d) CH,-F< CH;-Cl> CH-Br > CH NEEN
(b) Phenol, NaNO, HCI, CuCI 8. The major product of the following

HCIon (d)t NH,ay

otago
HCl,heating

(NEET)
ÇH,
CI
NaOH
reaction is

3. The major product formedin dehydrohalogenation CzH,OH >Major productaansi

E reaction of 2-bromopentaneis pent-2-ene. This
cproduct formation is based on? (a)
CHicn (b)
(a) Huckel's Rule (b) Saytzeff's Rule
(c) Hund's Rule (d) Hofmann Rule(NEET) ÇH,
ÇH, OH
4. The incorrect statement regarding chirality is (c) (d) (JEE Main)
(a) Sl reaction yields 1: 1 mixture of both
enantiomers HO
(b) the product obtained by S2 reaction of CH, CH,
odttp 9. IUPAC name
haloalkane having chirality at the reactive site of CH,C-(-CH, iS

shows inversion of configuration

CH,
O c) enantiomers are superimposable mirror images Clstudiyiisie-S
-of each other (a) 3-chloro-2, 2, 3-trimethylbutane
olsld
(b)
(d) a racemic mixture showszero optical rotation. 2-tert-butyl-2-chloropropane
E (c) l-chloro-1, 1-dimethyl-2,2-dimethylpropane
saS (NEET)
5. H(d) 2-chloro-2, 3, 3-trimethylbutane.(JIPMER)
Product A of following sequence of reactions is

Ethylbenzene
() Br, Fe 10. The hydrolysis reaction that takes place at the
A
(ii) Cl,, A slowest rate, among the following is
Major Product
(ii) alc. KOH
boe (h) -C NaOH
Br (a) 49,
-ONa
C=CH,hblet sinsy c=cH,0.0
obog CH,esoCH,
b (a) (b) aq. NaOH
boz diiw (0) HC-CH ClH,C-CH,-OH
HÇ=CH, aq. NaOH,
on (c) H,C=CHCH,CI
(c)
H,C=CH-CH,0H

Br Br
(JEE Main)
)CH,a: aq. NaOH
CH,OH (NEE)
 Chemistry
|
Correct
Haloalkarnes and Haloarenes

order for reaction with alcoholic KOH is o If assertion is

245

(c) true but reason is false.

(d) If both assertion andreason are false. (AlMS)
Br Br
(i) () (ii) (iv) 14. The compounds A and B in the following reaction
(a) i> ii> iii > iv (b) i> iii > ii > iv are respectively
(c) iv > ii> iii> (d)i>iv > ii > iii(AlIMS)
i
HCHO + HCI,A ABNB
The compound C,H undergoes the following
12.
reactions : (a) =benzyl chloride, B =benzyl isocyanide
A

A (b) =benzyl alcohol, B =benzyl isocyanide

A
3Cl,/A Br,/Fe
>B Zn/HCly C
C,Hs (c) A =benzyl alcohol, B =benzyl cyanide
The product C is (d) A = benzyl chloride, B = benzyl cyanide
(a) m-bromotoluene (JEE Main)
(b)o-bromotoluene 15. The major product of the following reaction is
ic) 3-bromo-2,4,6-trichlorotoluene Br.

(NEET) KOH alc. (excess)

(d) p-bromotoluene.
Ph
13. Assertion :Chlorobenzene is more reactive than
Br
benzene towards the electrophilic substitution reaction.

Reason:Resonance destabilises the carbocation.

(a) Ph
(a) If both assertion and reason are true and (b) Ph
reason is thecorrect explanation of assertion.
(b) Ifboth assertion and reason are truebut reason
(c) Ph (d) Ph (JEE Main)
is not the correct explanation
of assertion.
 ANSWER KEY
MCQs Corner
2. (d) 3. (d) 4. (c) 5.
(d) (b) 6. (a) 7.
1. (b) 8. (a) 9.
18. (c) 19. (c) 10. (d)
(b) 17. (c) (c) 20. (b) 21. (b) 11. (d)
. (b)
12.
16. 22. (a) 23. 13. (c) 14. (a)
33. (d) 24. (a) 15.(a)
(b) (a)
32. (c) 34. (d) 35. (b) 36. (d) 37. 25. (a) 26. (a) 27. (b) 28. (c)
31.

.
46. (d)
47. (d) 48. (b) 49. (b) 50. (a) 51. (c) 52.
62. (c) 63. (d) 64. (a) 65. (d) 66.
(a) 38. (d)

(a) 53. (c)

39. (c) 40. (c) 41.
54. (d) 55. (c) 56.
(d) 42. (a) 43.

(b)
29. (b)
(b) 44. (b)
30. (d)

45. (a)
61. (b) (a) 67. (b) 68. (a) 69. (a)
57. (b) 58. (c)
59. (d) 60. (a)
70. (b) 71. (b)
76. (d)
77. (b) 78. (b) 79. (b) 80. (d) 81. (a) 72. (c) 73. (c) 74. (b)
82. (b) 83. (a) 84. (b) 75. (c)
92. (b) 93. (c) 94. (b) 95. (c) 96. 85. (b) 86. (a) 87. (a) 88. (a) 89.
91. (a) (b) 97. (c) 98. (c) 99. (b) 90. (b)
(d)
100.(d)om 9r heioe9
NCERT Exemplar Problemsvc
2. (d) 3.
(a) 4.. (b) 5. (a) 6. (a) 7.
(a) 8. (c) 9. (b) 10.
)
17. (d) 18. (c) 19. (b)
20. (d) 21. (c) 22. (a) 23.
(a) 11. (b) 12. (a) 13.
(b) 14. (b) 15. (c)
(a) 24. (b) 25. (a)
26. (c) 27. (d) 28. (d) 29. (c)
31.(d) 30. (a)

Exam Scorer HOHD

A &R Corner
L (c) 2. (a) 3. (c) 4. (a) 5. (d) 6. (a) 7. 8.
(c) (a) 9. (c) 10. (d) 11. (c) 12. (d) 13.
Case Based Questions (c) 14. (b) 15. (b)

1. (a) 2. (b) 3. (d) 4. (b) 5. (d) 6. (b) 7. (b) 8. (d) 9. (c) 10. (a)
Numerical Value Type Questions
1. (3) 2. (4) 3. (2) 4. (5) 5. (1)
Thinking Corner
1. (a) 2. (b) 3. (d) 4. (b) 5. (6) 6. (b)

Exam Archive
oteol&ik
1. (b) 2. (a) 3. (b) 4. (c) 5. (d) 6. (d) 7. (c) 8. (b) 9. (d) 10. (a) 11. (b) 12. (a) 13. (d) 14. (a) 15. (a)