CLASS XII CHEMISTRY CHAPTER WISE QUESTION PAPER
UNIT : HALOALKANES AND HALOARENES
MAX MARKS:70 TIME:03 hours
General Instructions:
(a) There are 35 questions in this question paper.
(b) SECTION A consists of 18 multiple choice questions carrying 1 mark each.
(c) SECTION B consists of 07 very short answer questions carrying 2 marks each.
(d) SECTION C consists of 05 short answer questions carrying 3 marks each.
(e) SECTION D consists of 02 Case based question carrying 4 marks each.
(f) SECTION E consists of 03 long answer questions carrying 5 marks each.
(g) All questions are compulsory.
(h) Use of log tables and calculators not allowed.
Section A
Q.1 In which of the following molecules carbon atom marked with asterisk (*) is 1
asymmetric?
(A) (a), (b), (c), (d)
(B) (a), (b), (c)
(C) (b), (c), (d)
(D) (a), (c), (d)
Q.2 Chlorobenzene is formed by reaction of chlorine with benzene in the presence of
1
AlCl3. Which of the following species attacks the benzene ring in this reaction ?
(A) Cl–
(B) Cl+
(C) AlCl3
(D) [AlCl4]–
Q.3 Identify following 1
reaction:
A) Wurtz Reaction
B) Etard Reaction
C) Reimer Tiemann
Reaction
D) Kolbe Reaction
Q.4 The reaction of toluene with chlorine in the presence of iron and in the absence of
1
light yields ____________.
A) Benzyl chloride
B) o-Chlorobenzene
C) p-Choloro benzene
D) Mixture of B and C
1
Q.5 What is Q in the following reaction?
Q.6 Which of the following is the correct order of decreasing SN2 reactivity? 1
A) RCH2X > R2CHX > R3CX
B) R3CX > R2CHX >RCH2X
C) R2CHX >R3CX > RCH2X
D) RCH2X >R3CX >R2CHX
Q.7 Which of the following is correct for the reaction 1
a) A is major product and B is minor product
b) B is major product and A is minor product
c) Only A will be obtained as a product
d) Only B will be obtained as a product
Q8 Tertiary alkyl halides are practically inert to substitution by SN 2 mechanism 1
because of
(A) steric hindrance
(B) inductive effect
(C) instability
(D) insolubility
Q.9 Match the reactions given in Column I with the names given in Column II.
1
A) i-a, ii-b ,iii-c, iv-d
B) i-b, ii-a , iii-d, iv-c
C) i-d, ii-b ,iii-c, iv-a
D) i-c, ii-a ,iii-b, iv-d
2
Q.10 Alkyl fluorides are synthesised by heating an alkyl chloride/bromide in presence of_
1
(A) Ca F2
(B) PF3
(C) Hg2F2
(D) NaF
Q.11 Haloalkanes contain halogen atom (s) attached to the sp3 hybridised carbon atom
1
of an alkyl group. Identify haloalkane from the following compounds.
(A) 2-Bromopentane
(B) Vinyl chloride (chloroethene)
(C) 2-chloroacetophenone
(D) chlorobenzene
Q.12 Alkyl halides are prepared from alcohols by treating with______
1
(A) HCl + ZnCl2
(B) Red P + Br2
(C) PCl5
(D) All the above
Q.13 Match the structures given in Column I with the names in Column II.
1
A) i-a, ii-b ,iii-c, iv-d
B) i-b, ii-a, iii-d, iv-c
C) i-d, ii-b ,iii-c, iv-a
D) i-a, ii-d, iii-c, iv-b
Q.14 Which is the correct increasing order of boiling points of the following compounds?
1
1-Iodobutane, 1-Bromobutane, 1-Chlorobutane, Butane
(A) Butane < 1-Chlorobutane < 1-Bromobutane < 1-Iodobutane
(B) 1-Iodobutane < 1-Bromobutane < 1-Chlorobutane < Butane
(C) Butane < 1-Iodobutane < 1-Bromobutane < 1-Chlorobutane
(D) Butane < 1-Chlorobutane < 1-Iodobutane < 1-Bromobutane
3
Given Given below question no 15-18 consist of an "Assertion" (A) and "Reason" (R) Type 1
questions. Use the following Key to choose the appropriate answer.
A.If both (A) and (R) are true, and (R) is the correct explanation of (A).
B.If both (A) and (R) are true but (R) is not the correct explanation of (A).
C.If (A) is true but (R) is false.
D.If (A) is false but (R) is true.
Assertion : Presence of a nitro group at ortho or para position increases the
Q.15
reactivity of haloarenes towards nucleophilic substitution.
Reason : Nitro group, being an electron withdrawing group decreases the electron
density over the benzene ring.
Q.16 Assertion : It is difficult to replace chlorine by –OH in chlorobenzene in comparison 1
to that in chloroethane.
Reason : Chlorine-carbon (C—Cl) bond in chlorobenzene has a partial double bond
character due to resonance.
Q.17 Assertion: Chlorobenzene is less reactive than benzene towards the electrophilic
substitution reaction.
Reason: Resonance destabilises the carbo cation.
Q.18 Assertion:The C–Cl bond length in chlorobenzene is shorter than that in CH3–Cl.
Reason: In haloarenes Cl is attached to sp2 hyridised carbon which is more
electronegative than sp3 hybridised carbon.
Section B
Q.19 Hydrolysis of optically active 2-bromobutane forms optically inactive 2
butan-2-ol. Why?
Q.20 a)Which one out of CH3CH(Cl)CH2CH3 and CH3CH2CH2CH2Cl is more easily 2
hydrolysed by KOH(aq).
b) Arrange the following compounds according to reactivity towards nucleophillic
substitution reaction with CH3ONa
4- nitro chloro benzene, 2,4 di nitro chloro bemzene, 2,4,6, trinitrochlorobenzene
Q.21 Vinyl chloride is less reactive than allyl chloride. Why? 2
Q.22 How is chlorobenzene prepared by (a) direct chlorination (b) diazotization method? 2
Q.23 Why do haloalkenes under go nucleophillic substitution whereas haloarenes 2
under go electophillic substitution ?
Q.24 What happens when 2
a) Thionyl chloride acts upon propan-1-ol.
b) Ethanol reacts with PBr3 .
Q.25 What are the IUPAC names of the insecticide DDT and benzenehexachloride? Why is 2
their use banned in India and other countries?
Section C
Compound ‘A’ with molecular formula C4H9Br is treated with aq. KOH solution. The
Q.26 rate of this reaction depends upon the concentration of the compound ‘A’ only. 3
When another isomer ‘B’ of this compound was treated with aq. KOH solution, the
rate of reaction was found to be dependent on concentration of compound and KOH
both. (i) Write down the structural formula of both compounds ‘A’ and ‘B’. (ii) Out
of these two compounds, which one will be optically active?
4
Q.27 What is the difference between enantiomers and diastereomers. Illustrate with 3
one example.
Q.28 Some alkylhalides undergo substitution whereas some undergo elimination reaction 3
on treatment with bases. Discuss the structural features of alkyl halides with the
help of examples which are responsible for this difference?
Q.29 Give the IUPAC names of the following:- 3
(a) o-Br-C6H4CH(CH3)CH2CH3
(b) CH3C(Cl)(C2H5)CH2CH3
(c) Cl-CH2 C ≡ C-CH2-Br
Q.30 Complete the following reactions : 3
i) CH3CH=C(CH3)2 + HBr -------
ii) CH3CH2CH2OH + SOCl2 -----------
iii) CH3CH2Br + Mg ---------
Section D
Chloroflouro carbon (CFC) compounds of methane and ethane are collectively
Q.31 known as freons. They are non-inflammable , extremely stable, non-toxic, non- 4
corrosive and low boiling liquids. CFC and gas emitted from the exhaust system of
supersonics aeroplanes might be slowly depleting the concentration of the ozone
layer in the upper atmosphere. Answer the following questions on the basis oy
your knowledge .in this topic
1. Write the formula of freon.
2. Give two uses of chloroflourocarbons.
3. How does freon-12 deplete ozone layer?
4. Do you think the use of CFCs should be banned? Give reason.
Q.32 Methyl chloride, methyl bromide, ethyl chloride and some chlorofluoromethanes are 4
gases at room temperature. Higher members are liquids or solids. As we have
already learnt, molecules of organic halogen compounds are generally polar. Due to
greater polarity as well as higher molecular mass as compared to the parent
hydrocarbon, the intermolecular forces of attraction (dipole-dipole and van der
Waals) are stronger in the halogen derivatives. That is why the boiling points of
chlorides, bromides and iodides are considerably higher than those of the
hydrocarbons of comparable molecular mass. The attractions get stronger as the
molecules get bigger in size and have more electrons.
i)Draw all the possible isomers structure of bromobutane and arrange them in
increasing order of boiling points. (2 marks)
ii)Even though haloalkanes are polar compounds these compounds are least
soluble in water. Why?(1 mark)
iii) How will you distinguish between chloroethane and bromoethane?(1 mark)
Q.33 i)Identify A, B , C, D and E in the following:- 5
+SOCl2 AlcKOH HBr/Peroxide AgCN
CH3CH2CH2OH ──────→ A ──────→ B ───────→ C ───────→ D
KCN
5
Section E
Q.34 i) Arrange in increasing order of boiling points.
(a) Bromomethane, Bromoform, chloromethane, Dibromo-methane 5
(b)1-chloropropane, Isopropyle chloride, 1-Chlorobutane.
(c) 1-chloropropane, , 1-bromopropane, 1-iodopropane
ii) Which compound will react faster in SN2 reaction with OH---?
(a) CH3Br and CH3I (SN2)
(b) (CH3)3C-Cl or CH3Cl (SN2)
Q.35 How the following conversions can be carried out? 5
i) But-1-ene to n-butyliodide
ii) 2-Chloropropane to 1-propanol
iii) Isopropyl alcohol to iodoform (iv)
iv) Chlorobenzene to p-nitrophenol
v) 2-Bromopropane to 1-bromopropane
6
CLASS XII CHEMISTRY CHAPTER WISE QUESTION PAPER
UNIT : HALOALKANES AND HALOARENES - ANSWER KEY
MAX MARKS:70 TIME:03 hours
1B 2B 3C 4D 5C 6B 7A 8A 9B
10 C 11 A 12 D 13 A 14 A 15 A 16 C 17 A 18 B
Q.19 Due to the formation of planar carbocation as intermediate in SN1 mechanism, OH- 2
can attack carbocation equally from both side which result in racemic mixture.
Q.20 a) CH3CH(Cl)CH2CH3 2
b) 2,4,6, trinitrochlorobenzene > 2,4 dinitrochlorobemzene > 4- nitrochlorobenzene
Q.21 Vinyl chloride is less reactive than allyl chloride, it is due to resonance in vinyl 2
chloride the C- Cl bond gets double bond character and becomes stable.
Q.22 a) 2
b)
Q.23 Due to more electro negative nature of halide atomC-X bond is polar in haloalkanes 2
and carbon atom becomes slightly positive and is easily attacked by nucleophillic
reagents. While in haloarenes due to resonance, carbon atom becomes slightly
negative and attacked by electrophillic reagents.
Q.24 (a) When thionyl chloride acts upon 1- propanol chloropropane is formed . 2
(b) When ethanol reacts with PBr3, bromoethane is formed
Q.25 Correct name. 2
Q.26 A. 1-Bromo butane. B) 2-Bromo butane. B is optically active. 3
Q.27 Enantiomers are those optical isomers of optically active compound which are 3
non-superimposable images of each other.
Diasteriomers are those optical isomers optically active compound which are non-
superimposable but not mirror images of each other.
Any one example.
Q.28 Primary alkyl halides undergo substitution reaction where as tertiary alkyl halides 3
undergo elimination reactions.
Q.29 Correct Name 3
Q.30 i)CH3CH2CH(Br)CH3 ii) CH3CH2CH2Cl +SO2+HCl iii)CH3CH3 3
7
Q.31 1 CCl2F2 4
2 It is used in air conditioning and in domestic refrigeration for cooling purposes.
3 Freons can diffuse into the stratosphere and in stratosphere, freon is able to
initiate radical chain reactions by using UV rays that can upset the natural ozone
balance.
4 CFCs should be banned and its alternative should be used which would be safer
and has no environmental impact.
Hydrochloroflourocarbons and Hydroflourocarbons are some halogen containing
compounds are useful in daily life. Some compounds of this class are responsible
for exposure of flora and fauna to more and more of UV light which causes
destruction to a great extent. Name the class of these halocompounds.
Q.32 i) All the isomers and correct order 4
ii) When haloalkanes dissolved in water they neither form hydrogen bond nor they
can release sufficient energy to break the hydrogen bond in water.
iii)They can be distinguished by silver nitrate test ( treating with aq.NaOH followed
by AgNO3 ). Chloroethane gives white ppt of AgCl (soluble in ammonium hydroxide)
but bromo ethane gives pale yellow ppt of AgBr (partially soluble in ammonium
hydroxide)
Q.33
A) CH3CH2CH2Cl , B) CH3CH=CH2 , C)CH3CH2CH2 OH ,
D) CH3CH2CH2NC E) CH3CH2CH2 CN 5
Q.34 i) (a) chloromethane < Brommethane < Dibromo-methane < Bromoform
(b) Isopropyle chloride <1-chloropropane <1-Chlorobutane
(As Branching increases , boiling point decreases) 5
(c)1-Chloropropane< 1-Bromopropane< 1-iodopropane
ii) (a) CH3I will react faster than CH3Br
(b) CH3Cl will react faster than 30 halide
Q.35 (i)
5
(ii)
8
(iii)
(iv)
(v)
