CASE BASED/SOURCE BASED

INTEGRATED QUESTIONS
question,has an internal choice and carries 4(1 +1+ 2) marks.
fach
o1 Read he passage given below and answer the
following questions :
Physical properties : Alkyl halides are colourless when present in pure state. However, bromides
and iodides develop colour when exposed to light. Lower halides are gases at room temperature,
higher members are liquids and solids. Dipole-dipole and van der Waals forces of attraction are
stronger in halogen compounds compared to the respective hydrocarbons. Thatmass. is why their
boiling points are higher compared to hydrocarbons of comparable molecular For the
: RI > RBr > RCl >RE.
same alkyl group the boiling points of alkyl halides decrease in the order points of
Boiling points of isomeric haloalkanes decrease with increase in branching. Boiling
melting as
jsomeric dihalobenzenes are very nearly the same. However, the para-isomers are high better
crystal lattice
compared to their ortho and meta-isomners. In para isomers the molecules fit in
increases with increase in
as compared to ortho- or meta-isomers. Density of halogen compounds dissolve
the number of carbon atoms. Solubility of haloalkanes in water is very low, however, they
in organic solvents.
() Why is the solubility of haloalkanes in water very low ?
() Which of the following compounds will have the highest melting point and why ?
o-dichlorobenzene, m-dichlorobenzene and p-dichlorobenzene.
(ii) C-CI bond length in chlorobenzene is shorter than C-CI bond length in CH, - Ci.
Why ?
Or
Why the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride ?
Ans. () Haloalkanes do not form hydrogen bond with water.
(ii) It will be p-dichlorobenzene. It is due to the reason that it has symmetrical structure and,
therefore, forms a stable crystal lattice.
:0:
(ii) CH,-CI
Electrons on Cl in chlorobenzene take part in resonance with the benzene ring. This creates a
partial double bond character between C and Cl in chlorobenzene. As a result, C-Cl bond
length in chlorobenzene is shorter than in methyl chloride, which does not involve resonance.
Or
:: :ä:

Chlorobenzene Cyclohexyl chloride

Chlorine is more electronegative than carbon. This creates a positive charge on carbon
linked to C in cyclohexyl chloride. In chlorobenzene the electrons on chlorine participate
in resonance with the ring. This decreases separation of charges. Hence dipole moment of
chlorobenzene is lower than that of cyclohexyl chloride.
a. Kead the passage given below and answer the following questions :
Saytzeff observed that in dehydrohalogenation reactions, the preferred product is that alkene
which has the greater number of alkyl groups attached to the carbon-carbon double bond. Thus in
ne dehydrohalogenation of 2-bromopentane, pentene-2-ene is the preferred product.
Haloalkanes and Haloarenes 277
 An alkyl halide with a-hydrogen atom when reacted with a base or a
Competing routes : substitution (SE1 and SN2) and elimination. The actual nucleophile
route taken has two
upon the nature of the alkyl halide, strength and size ofthe base. Abulkier
to act as a base and abstract a proton rather than approach a tetravalent nucleophile
carbon
will prefer depends
reasons. Aprimary alkyl halide will prefer SN2 reaction, a secondary halide SE2 atom or
for steri
depending upon the strength of the base and atertiary halide - Sy1 or elimination eliminatio
the stability of the carbocation or the substituted alkene.
(i) What is nucleophile ?
upondepending
(ii) Write one example of dehydrohalogenation reaction.
(i) Vinyl chloride is unreactive to nucleophilic substitution reactions. Why ?
Or
Some alkyl halides undergo substitution reaction whereas
some undergo eliminaian
reaction on treatment with bases. Discuss the structural features of alkyl
halide with h.
help of example which are responsible for this difference.
Ans. (1) A nucleophile is either a negatively charged or
neutral
which has got affinity for the nucleus. For examnple, "OH,species
: NH3
having lone pair of electrons.
(i)
Br
Alc. KOH |
CH;CH,CH=CH-CH, H,CCH,-CH,CHCH, Alc. KOH
Heat
Heat
CH,CH,CH,CH=CH
Pent-2-ene (81%) H
2-Bromopentane Pent-1-ene (19%)
(iii) Vinyl chloride involves resonance as shown
below :
CH,CH CI: CH,CH=C|:
As a result, C - Cl bond in it acquires a
partial double bond character. Hence, C -Cd
bond is shorter and more stable so that vinyl
chloride is unreactive to nucleophiles.
Or
An alkyl halide, with hydrogen atom on carbons
has two competing routes : substitution and neighbouring to halogen carrying carbon,
upon the nature of alkyl halide, strength and sizeelimination. The actual route taken depends
of base/nucleophile and reaction conditions
Thus a bulkier nucleophile like C4H,0 will prefer to act as a
rather than approach a tetravalent carbon atom due to base. It will abstract a proton
steric reasons. On the contrary, a
smaller nucleophile will atach itself to the carbon
A primary alkyl halide will prefer a Sy2 carrying the halogen.
reaction, a secondary halide will tend to give Sy20
elimination reaction depending upon the strength of the
halide will give SN or elimination reaction depending base/nucleophile and a tertiary alky
upon the stability of the carbocatio
or the more substituted alkene.

MULTIPLE CHOICE QUESTIONS

Select the correct option(s) out of the four possible options given after the statement of the question:
0.1. Which of the following is most reactive towards nucleophilic substitution reaction ?
[CBSE2022)
CI C CI
NO, NO, O,N NO;
(a) (b) (c) (d)

NO, NO,
U-LIKE Chemistry-X
278
 0.2. In the following reaction:
CH, - Br dry Mg
ether
X H,0
Y will be:
(a) CH4 (b) CH,MgBr [CBSE 2022]
(c) CH,- OH (a) CH,-CH,
0.3. Which of the following compounds undergoes racemisation
KOH? on hydrolysis with aqueous
(a) CH, - CH,- Br [CBSE 2022]
(b) CH, -CH CH, Br
CH3

(c) CH, - Br (d) CH¡ CH-Br

0.4. The IUPAC name of isobutyl bromide is :
[CBSE 2022]
(a) -bromo-3-methylbutane (b) 3-bromo-2-methylpropane
(0) 2-bromo-2-methylpropane (a) -bromo-2-methylpropane
0.5. Chlorobenzene when treated with sodium in dry ether gives
(a) Wurtz reaction
Diphenyl. It is called:(CBSE 2022]
(b) Fittig reaction
(c) Wurtz-Fittig reaction (d) Friedel-Crafts reaction
Q.6. Consider the following reaction :
[CBSE 2022]
1. HBr
CH, CH=CH, 2. aq. KOH
The major end product is
(a) CH3-CH-CH3 (b) CH3-CH-CH,
OH Br

(c) CH,-CH,CH, OH (a) CH,-CH CH, Br

Q.7. Which one of the following halides contains Cs- Xbond ?
[CBSE 2022]
(a) Allyl halide (b) Alkyl halide (c) Benzyl halide
Q.8. Consider the following (4) Vinyl halide
compounds : [CBSE 2022]

a(-ct-a(a
The correct order of reactivity towards Sy2 reaction
(a) I> II > II (b) II > II > I (c) II > I> II (d) III > I> II
Q9. Major product formed in the following reaction :
[CBSE 2022]
CH3
CH3-C- Br + NaOCH;
CH,
CH3 CH3
(a) CH3 -C-ONa (b) CH3-C 0CH,
CH3 CH,

Haloalkanes and Haloarenes 279

 CH,
CH3 CH3
(d) CH,-C=CH,
(c) CH;-C-0 C-CH3

CH3 CH3
Q.10. Enantiomers differ only in (b) rotation of polarised light. |CBSE. 202
(a) boiling point.
() melting point.
(d) solubility.

Q.11. In the reaction Br Mg X

H,0 ’ Y.Compound 'Y is (CBSE 202
dry ether

(a) -OH (b) (c)

Q.12. Which of the following has highest boiling point ? (CBSE 202
(a) C,Hs-F (b) C,H; -CI (c) CH_ - Br (d) CzH,-I
isomeric monochlorides a
Q.13. Which of the following isomer of pentane (CçH) will give three
photochemical chlorination ? (CBSE 2022)
CH,
(a) CH,-C-CH, (b) CH,CH,CH,CH,CH,

CH,
(d) All of the above
(c) CH3--CH-CH,-CH3
CH3
Q.14. Which of the following isomer has the highest melting point ? [CBSE Sample Question Paperl
(a) 1, 2-dichloro benzene (b) 1, 3-dichlorobenzene
(c) 1,4-dichloro benzene (d) Allisomers have same melting points
HBr in presence of organic
Q.15. Major product obtained on reaction of 3-Phenyl propene with[CBSE
peroxide
Sample Question Paper
(a) 3- Phenyl 1-bromopropane (b) 1-Phenyl -3- bromopropane
(c) 1-Phenyl -2-bromopropane (d) 3-Phenyl -2- bromopropane
0.16. Which of the following is a correct statement for C,H,Br ? [CBSE Sample Question Paper
(a) It reacts with metallic Na to give ethane.
(b) It gives nitroethane on heating with aqueous solution of AgNO,.
(c) It gives C,H,OH on boiling with alcoholic potash.
(d) It forms diethylthioether on heating with alcoholic KSH.
to toluene?
Q.17. Which reagents are required for one step conversion of chlorobenzene Sample Question Papel
ICBSE
(a) CH,CI/AICl, (b) CH,CI, Na, Dry ether
(c) CH,CI/Fe dark (d) NaNO,/HCI/0 -5 °C
toluene withCl,in
Q.18. The reaction of toluene with CI, in presence of FeCl, gives 'X whileSample
the OuestionPaperl
presence of light gives Y. Thus 'X and 'Yare: ICBSE
(a) X = benzyl chloride Y=0 and p-chlorotoluene
(b) X = m-chlorotoluene Y= p-chlorotoluene
(c) X =0 and p-chlorotoluene Y= trichloromethyl benzene
(d) X = benzyl chloride, Y = m-chlorotoluene

U-LIKEChemistry-Xl
280
Q.19.
Alkenes decolourise bromine water in presence of CCl, due to formation of :
[CBSE Sample Question Paper)
(a) allyl bromide (b) vinyl bromide (c) bromoform (d) vicinal dibromide
Complete the following analogy :
Q.20.
Csme molecular formula but different structures :A: Non superimposable mirror images : B
[CBSE Sample Question Paper]
(a) A:Isomers B: Enantiomer (b) A:Enantiomers B: Racemic mixture
(c) A:Sterioisomers B: Retention (d) A: Isomers B : Sterioisomers
produces
021. Chloroform on exposure to air in the presence of light
(a) phosphoryl chloride. (b) phosphine.
() phosphorus oxytrichloride. (a) phosgene.
gives
022. Chlorobenzene reacts with alkyl chloride in the presence of sodium metal
(a) toluene. (b) xylene. (c) phenol. (d) benzyl chloride.
0.23. Which of the following statements about DDT is incorrect ?
(a) Many species of insects developed resistance to DDT.
(b) DDT is safe to use as insecticide.
(c) It has a high toxicity towards fish.
(a) DDT is not metabolised rapidly by animals.
0.24. Which of the following is not used for the preparation of alkyl halides from alcohols ?
(a) Cl, (b) HCI/ZnCl, (c) PCls (a) SOCI,
Q.25. Which of tte following is least reactive towards Sy2 reaction ?
(a) CHX (b) Primary halide
(c) Secondary halide (a) Tertiary halide
Q.26. Alkyl iodides are often prepared by the reaction of alkyl chlorides/bromides with Nal in dry
acetone. This reaction is known as
(a) Wurtz reaction. (b) Finkelstein reaction.
(c) Grignard reaction. (d) Sandmeyer's reaction.
Q.27. Which of the following has the least boiling point ?
(a) CH,CH,Br (b) CH;CH,CHCH,
CH3
CH,
() CH,CH,CH,CH,Br (d) H,C-Ç-CH
Br
e0 Vinylic halides are compounds in which the halogen atom is bonded to sp hybridised carbon
atom of
(a) an alkane. (b) an alkene. (c) an alkyne. (d) an aromatic ring.
Q.29. Propene on treatment with HI gives
(a) Only CH,CH,CH,l
(b) Only CH,CHICH,
C) CH,CH,CH,I(minor) +
a) CH,CH,CH,I(major) + CHCHICH,(major)
Q30. CHCHICH,(minor)
Treatment of toluene with a halogen in dark in the presence of Fe gives
(a) o-Halotoluene.
(b) p-Halotoluene.
(c) m-Halotoluene.
(d) Mixture of o- and p-Halotoluene.

Haloalkanes and Haloarenes 281

Q.31. Molecules whose mirror image is non superimposable over them are known as
chiral,
the following molecules is chiral in nature ?
(a) 2-Bromobutane (b) 1-Bromobutane (c) 2-Bromopropane (a) .Whwhy
Q.32. Which ofthe following compounds will give racemic mixture on nucleophilic:
OH ion ?
2-Bromoprsoupbasnit-u2ti-md h
Br

() CH,-CH Br (ii) CH,-C-CH (ii) CH¡-CH-CH,Br

CzHs C,H5
(a) () (b) (i), (i), (iin) (c) (i), (ii) (d) (), (üin)
Q.33. Which of the following are secondary bromides ?
(a) (CH),CHBr (b) (CH)CCH,Br
() CH,CH(Br)CH,CH, (4) (CH),CBrCH,CH,
Q.34. Reaction of C,H,CH,Br with aqueous sodium hydroxide follows
(a) Syl mechanism
(b) SE2 mechanism
(c) any of the above two depending upon the temperature of reaction
(a) Saytzeff rule
Q.35. Toluene reacts with a halogen in the presence of Fe() chloride giving ortho and pars bal
compounds. The reaction is
(a) electrophilic elimination reaction. (b) electrophilic substitution reaction.
(c) free radical addition reaction. (d) nucleophilic substitution reaction.
Q.36. Chloromethane on treatment with excess of ammonia yields mainly
(a) N, N-Dimethylmethanamine (CH,- N)
(b) N-methylmethanamine (CH, NH CH)
(c) Methanamine (CH,NH,)
(d) Mixture containing all these in equal proportion
Q.37. Which of the carbon atoms present in the molecule given below are asymmetric?
OH H
OH Ib le d
C-C
H
OH
(a) a, b, c, d (6) b, c (c) a, d (d) a, b, c
Q.38. Which of the following compounds are gem-dihalides ?
(a) Ethylidene chloride (b) Ethylene dichloride
(c) Methylene chloride (d) Benzyl chloride
Q.39. Which of the following is an example of vic-dihalide ?
(a) Dichloromethane (b) 1, 2-dichloroethane
(c) Ethylidine chloride (d) Allylchloride
Q.40. Which reagent would you use for the following reaction ?
CH,CH,CH,CH, CH,CH,CH,CH,Cl + CH,CH,CHICH,
(a) Cl,/UV light (b) NaCl + H,SO4 in
dark
(c) Cl, gas in dark (d) Cl, gas in the presence of iron
U-LIKE Chemistry
282
 ANSWERS
1. (d) 2. (c) 3. (d) 4. (d) 5. (b) 6. (a) 7. (d) 8. (c)
9. (d) 10. (b) 11. (c) 12. (d) 13. (b) 14. (c) 15. (b) 16. (b)
17. (b) 18. (c) 19. (d) 20. (a) 21. (d) 22. (a) 23. (b) 24. (a)
25. (d) 26. (b) 27. (a) 28. (b) 29. (c) 30. (d) 31. (a) 32. (a)
33. (a) and (b) 34. (a) 35. (b) 36. (c) 37. (b) 38. (a) and (c)
39. (b) 40. (a)

ASSERTION-REASON QUESTIONS
Note - Read the following instructions carefully :
(a) Both Assertion (A) and Reason (R) are correct statements, and Reason (R) is the correct explanation of
the Assertion (A).
(b) Both Assertion (A) and Reason (R) are correct statements, but Reason (R) is not the correct explanation
of the Assertion (A).
(c) Assertion (A)is correct, but Reason (R) is incorrect statement.
(d) Assertion (A) is incorrect, but Reason (R) is correct statement.
Q.1. Assertion (A):Aryl halides are extremely less reactive towards nucleophilic substitution
reaction.
Reason (R) : Halogen atom shows + I effect in Aryl halides. [CBSE 2022]
Q.2. Assertion (4): Chlorobenzene is less reactive towards nucleophilic substitution reaction.
Reason (R) : Nitro group in chlorobenzene increases its reactivity towards nucleophilic
substitution reaction. [CBSE 2022]
Q.3. Assertion (A) : Alkyl halides are insoluble in water.
Reason (R) : Alkyl halides have halogen attached to sp hybrid carbon.
[CBSE Sample Question Paper]
Q.4. Assertion (A) : In the case of optically active alkyl halide, the product formed as aresult of SN2
mechanism has the inverted configuration as compared to the reactant.
Reason (R) In Sy2 mechanism, the nucleophile attaches itself on the side opposite to the
one where the halogen is present resulting in inversion in configuration of the
product.
Q.5. Assertion (A) : Aracemic mixture is represented byfixing dl or (t) before the name.
Reason (R) : Aryl halides are extremely reactive towards nucleophilic substitutions.
Q.6. Assertion (A) : The stereoisomer's related to each other as non-super imposable mirror images
are called enantiomers.
Reason (R) : Butan-2-ol has four different groups attached to the tetrahedral carbon and is
chiral.
Assertion (4) : Alkyl halides are prepared by electrophilic halogenation of alkanes.
Reason (R) : DDT is a safe insecticide.
Q8. Assertion (4) : Halothane is used as an anaesthetic during surgery.
Reason (R) : The deficiency of iodine in our body causes goitre.

Haloalkanes and Haloarenes 283

 Q.9. Assertion (A) : The compounds in which the halogen atom is bounded to an sp
carbon atom adjacent to the carbon-carbon double bond are called hybridise
halides. vinylik
Reason (R) : Common names of alkyl halides are derived by naming the alkyl
folllowed by the name of the halide.
Q.10. Assertion (A) : Common name of CH,- CHCI, is ethylidene chloride.
Reason (R) : As we go down the group in the Periodic Table, the size of halogen aine
decreases.
Q.11. Assertion (A) : The minor product obtained in the reaction between CH,CH =CH, and PH
is CH,CH,CH,I.
Reason (R) : Alkyl bromides and iodides develop colour when exposed to light.
Q.12. Assertion (A):Boiling points of alkyl halides decreases in the order :
RI > RBr > RCI > RF
Reason (R) : Attractions get stronger as the molecules get bigger in size.
Q.13. Assertion (A) : A mixture containing two enantiomers in equal proportions is called a racemic
mixture.
Reason (R) : Compounds of the type RMgX were discovered by Sandmeyer.

ANSWERS
1. (c) 2. (b) 3. (b) 4. (a) 5. (c) 6. (b) 7. (d) 8. (b)
9. (d) 10. (c) 11. (b) 12. (a) 13. (c)

VERY SHORT ANSWER QUESTIONS

Each of the following questions are of 1 mark.
Q.1. Out of chlorobenzene and benzyl chloride, which one gets easily hydrolysed by aqueous Na0H
and why ? [CBSE201S
Ans. Bernzyl chloride gets easily
hydrolysed by aqueous NaOH.
C
CH,CI

Chlorobenzene
Bond between Cand Cl in benzyl chloride is easilyBenzyl chloride
broken. In chlorobenzene, the bond betweenC
and Cl acquires a double bond
Q.2. Write the structure of character because of resonance., It is not easily
broken. (Delhi2011
4 3
1-Bromo-4-chlorobut-2-ene.
H
Ans.
Cl-CH,-CH= CH-C Br
H

Q.3. Out of and lA..

2011
, which is an
example of allylic halide ?
284