Chapterwise CBSE Solved pers: CHEN

168 AEMIST
Draw the
structure of the followi
10. Write the IUPAC name of the following 22.
compound: -chlorophenyl)-2-
compound: propaneDelhi2011C
Cl of thne
IUPAC name
following
23. Write the
compound
H ,CH3
All India 2013 H
CH3 H Br
Cl
11. Write the IUPAC name of the following
AL india 20
24. Give the IUPAC name the followi
compound: compound:

CH-CH-CH-CH-CH H3C ,CHg

AllIndia2013 ,H
Br Cl H Br
12, A hydrocarbon C,Hg gives only one HC
monochlorination product. Identify the AllIndia 20
hydrocarbon. Delhi 2013C 25. Draw the structure ot the compound.
13. Give the IUPAC name of the following 4-tert-butyl-3-iodoheptane. AllIndia20100
compound: 26. Write the IUPAC name of the following
CH=C-CH,Br compound:
CH3
CH3 Delhi 2012
14. What happens when bromine attacks H,C-CCH,C1 All India 20100
CH,= CH-CH-C=CH? CH
Allindia 2012 27. Draw the structure of the compound,
15. Write the IUPAC name of the following 1-chloro-4- ethyleyclohexane. AllIndia2010
compound (CH, ), CCH,Br. Delhi2011 28. Draw the structure of the following
16. Write the IUPAC name of the following compound. 4-bromo-3-methylpent-2-ene.
compound: CH,=CHCH,Br. AllIndia2011 Foreign 2010
17. Draw the structure of 1,4-dibromobut-2-ene.
Delhi2011C; AllIndia 2010C 2 Marks Questions
18. Draw the structure of 2-(2-bromopheny) 29. Write the mechanism of the following
butane. Delhi2011C reaction:
19. Draw the structure of 2-(2-chlorophenyl)- HBr
1-iodooctane. AllIndio 2011C CH,CH,OH CH,CH,Br + H,0
Delhi 2014, All India 2014 C
20. Draw the structure of the following
30/Draw the structure of major monohalo
compound:
1-bromo-4-sec-butyl1-2-methylbenzene product in each of the following reactions

21. Draw the structure of the following

All India 2011C - OH sOCl2
organic compound:
2-chloro-3-methylpentane. -CH-CH=CH,+HBr Peroxid
AllIndia2011C AllIndia2014
 SOlved Papers: CHES
Chapterwise CBSE pers: CHEMIS CHAPTS

176
the major product formed
4. Predict h 12. W
ethoxide reacts with tert
sodium utyl
2.5 Polyhalogen Compounds W1
niNehloride. ceSE2018 C
used as chlorobenzene and benzyl chlon
(i) Dichloromethane (CH,Cl, ) is Out of 13. W
as remover. I t s hydroly
propellant in aerosols, paint which o n e gets easily rolysed by tr
causes nausea, NaOH and why? CBSE2018
exposure to higher levels aqueous 14W
dizziness. structure of an isomer of
6. Write the ur
methane are which is most
reacs
(7) The trihalogen derivatives of compound C,HgBr
reaction. AllIndia2016
called haloforms. towards Syl

e.g. CHCl, (Chloroform), CHI, (lodoform, CH-CH,-Cl and

7. Out of CH
used as an antiseptic)
coloured CH 15.
(iii) Chloroform is stored in dark
it gets CH-CH-CH-C1
bottles as in presence of light,
substance, 16. P
Converted into highly poisonous
CH3
phosgene (COCl,).
more reactive towards Sy 1
DDT is1, 1, 1-trichloro-2, 2-bis which is
(iv) used as a reaction and why? Delhi 2016 17.
(4-chlorophenyl)ethane and is
powerful insecticide. 8. Which would undergo SNl
reaction faster
the
is used as a fire extinguisher under in the following pair?
(V) CCl4 18.
name pyrene. CH-CH-CH-Br
used as a refrigerant.
(vi) Freon-12 (CF,Cl,) is and CH-CH-CH
Br AllIndia2015
reaction faster
19.
Previous Years 9. Which would undergo Sy 2
in the following pair and why?
Examination Questions CH
CH-CH,-Br and CH,-C-CH
1 Mark Questions 20
Br
1. Out of
Delhi 2015,Foreign 2015
-Cl and -CH Cl, Which would undergo S N2 reaction faster
10. 21.
in the following pair and why?
react faster in SN1 reaction
which will CH3-CH-Br and CH3-CH,
ith OH ? All India 2020 Foreign2015
at of CH,CH,CH,Cland
more
11 Identify the chiral molecule in the
which one is
H=CH-CHCl, following pair.
reactive towards Syl reaction? AllIndia 2020
and Cl
more reactive
3. Why is t-butyl bromide
towards Sy1 reaction as compared to Cl
20
n-butyl bromide? All India 2019 All India2014, Delhi
 CHEMIS CHAPTER 6: Haloalkanes and Haloarenes 177
ed whe
rt.bub 12. What happens when CH,-Br is treated 22, Write chemical equations whenr
with KCN? Delhi2013
y chlors i) ethyl chloride is treated with aqueous
ed by 13. What happens when ethyl chloride is KOH.
2018 treated with aqueous KOH? Delhi2013 (i) chlorobenzene is treated with
CH COCl in the presence of
er of 1 4 Which compound in the following pair anhydrous AlClg. Foreign 2014
t reactn undergoes faster towards Sy1 reaction? 23. ) Which alkyl halide from the following
16
Cl Cl pair would you expect to react more
nd rapidly by an Sy 2 mechanism and why?

Delhi 2013 CH-CH,-CH CH3

15. How methyl bromide be preferentially
Br
converted to methyl isocyanide? Delhi 2013 C
16. Predict the order of reactivity of four
CH-CH,-CH,-CH,-Br
(i) Racemisation occurs in Sy1 reactions.
isomeric bromobutanes in Syl reaction. Why? Foreign 2014
Sg1 Delhi 2012C 24. Which compound in each of the following
17. Which will react faster towards S2 pairs will react faster towards
tion faste reaction, 1-bromopentane or Sy2 reaction with--OH? Why?
2-bromopentane and why? Foreign 2011,2010 ) CH Br or CH,I
18. A solution of KOH hydrolyses (ii) (CH3 )s CCl or CH, CI
CH,CHCICH,CH, and CH,CH,CH,CH,CI Delhi2014, AI 2014, Al India 2010c
Which one of these is more easily 25. Write the chemical equations when,
ndia 2015 hydrolysed? Foreign2010; Delhi2010 ) methylchloride is treated with AgNO.
i) bromobenzene is treated with CH, Cl
19. Explain the following reaction with an
ion faste in the presence of anhydrous AICl3.
example: Friedel-Crafts reaction. Delhi 2010
Foreigin 2014)
CHs 2 Marks Questions
26. What are ambident nucleophiles? Give an
example. AllIndia2013;Foreign2012
C-CH 27.)Account for the following:
20, Which one of the following compounds is
more reactive towards Sy 2 reaction and ) The C-Cl bond length in
Br why? CBSE 2018 C chlorobenzene is shorter than that in
5, Foreign0 CH-Cl.
CH,CH(CI)CH,CH, or CH,CH,CH,C
tion faster (ii) Chloroform is stored in closed dark
21. ) Which alkyl halide from the brown bottles. Delhi2013
following pair is chiral and
CH undergoes faster towards SN2 28. Chlorobenzene is extremely less reactive
Foreign20 towards a nucleophilic substitution
reactions?
reaction. Give two reasons for the same.
he
(a) Br (b) Delhi 2013
Br 29. Explain why
(ii) Out of Sy l and S N2, which reaction ) alkyl halides, though polar, are
Occurs with immiscible with water?
314,Delhi20 (a) Inversion of configuration? ii) Grignard reagent should be prepared
(b) Racemisation? All India 2014 under anhydrous conditions?
Foreign 2012
178 Chapterwise CBSE Solved Papers:CHEMt
CHAPTER6 : Hc

STR (iii) S y 1 re

3 Marks Questions methyl chloride in the presencoof

sodium metal and dry ether.
r a c e m

xp halide

30. ) Write equation for preparation of iii) Write the structure of the alker 39/Howcan tl
1-iodobutane from 1-chlorobutane. formed by dehydrohalogenatior
1-bromo-1-methylcyclo) of
lohexane with
carried ou-

ii) Out of 2-bromopentane, 2-bromo-2

methylbutane and 1-bromopentane,
alcoholic KOH. cBSE 2018 ) Anili

(ii) Chlor
which compound is most reactive 34. Write the product(s) formed when
2-chl

towards elimination reaction and ) 2-bromopropane undergoes

(ii) Chlo
why? AllIndia2019 dehydrohalogenation reaction.
(iii) Give IUPAC name of (ii) Chlorobenzene dergoes
nitration
t t r A l n e

reaction. 40,What hap

CH3
is treated ) chlo

(iii) Methylbromide with

N
CH-CH= CH--C-CH CBSE 2018 Cl
(ii) ethy
given to yon
Br 35. Following compounds are
(ii) 2-br
All India 2019 2-bromopentane, 2-bromo-2-methylbuta alco
ne,
31, Give reasons for the following: 1-bromopentane Write the
(1) The presence of-NOg group at ortho ) Write the compound which is most of y o u r a
reactive towards Sy 2 reaction.
or para position increases the 41. Give rea=

reactivity of haloarenes towards ii) Write the compound which is

()n-bu
nucleophilic substitution reactions. optically active.
poir
(ii) p-dichlorobenzene has higher (iii) Write the compound which is most
reactive towards B-elimination (i) Racc
melting point than that of ortho or
meta isomer. reaction. Delhi 2017; All India 2017 (ii) The
at c
(iii) Thionyl chloride method is preferred How do you convert the following?
chloride from
36. rea
for preparing alkyl i) Chlorobenzene to bipheny
nuc
alcohols. AllIndia 2019 (ii) Propene to 1-iodopropane. Del
32 6)Out of (CH, , C--Br and (CH,)CL (iii) 2-bromobutane to but-2-ene. Delhi2015
towards 42.) ) WE
which o n e is m o r e reactive in the
37. Write the major product(s) wa
Sy1 and why?
/following: (i) WE
(ii) Write the product formed
when
) CH2 CH3 bu
p-nitrochlorobenzene is heated with Br2, UV light
(ii) Alm
443 K followed by
aqueous NaOH at
Wi
acidification. OgN
or
dextro and laevo-rotatory Na
(ii) Why (ii) 2CHs-CHCH ar
isomers of butan-2-ol are difficult
to Dry ether
W
distillation?
separate by fractional Cl
Delhi 2019 43. ) D-
AgCN m
33. () Identify the chiral molecule in the (ii) CH3-CH-Br Delhi 2015C
fo
following pair: 38. Give reasonas.
and (i) C-Cl bond length in chlorobenzene
is shorter than C-Cl bond length in
OH OH CH-CL1
i) ii) (i) The dipole moment of chlorobenzene
is lower than that of cyclohexyl
ii) Write the structure of the product chloride.
when chlorobenzene is treated with
 AEM CHAPTER 6: Haloalkanes and loarenes 179
ne d G) Syl reactions are accompanied by
Gi) Which halogen compound in each of
racemisation in optically active alkyl the following pairs will react faster
kene b halides. Foreign2015 towards Sy2 reaction?
e with 39/How can the following conversions be (a) CH Br or CH,I
carried out?
(6) (CH),C-Cl or CH-C
)Aniline to bromobenzene Delhi 2014
i) Chlorobenzene to 44 ) Which compound in each of the
on 2-chloroacetophenone following pairs will react faster
ii) Chloroethane to butane towards Sy2 reaction with-OH
itratit India2015c group?
th KO 40,What happens when (a) CH,Br or CHgI
CBSE ) chlorobenzene is treated with (6) (CH, ccl or CH,Cl
o you Cl /FeCl? i) Write the product(s) of the following
i) ethyl chloride is treated with AgNO,? reactions.
ylbuta (iii) 2-bromopentane is treated with (a) CHCl+ KCN ?
alcoholic KOH?
S most C1
Write the chemical equations in support CAnhyd. AICl+
n. of your answer. AllIndia2015 (b) +CH3-CI

41. Give reasons:

Delhi2014C
) n-butyl bromide has higher boiling
IS most point than t-butyl bromide. 45, Give reasons for the following:
on i) Racemic mixture is optically inactive. ) Ethyl iodide undergoes Sy 2 reaction
faster than ethyl bromide.
(i1) The presence of nitro group(-NO,)
(ii) () 2-butanol is optically inactive.
at o/p-positions increases the
reactivity of haloarenes towards (ii) C-X bond length in halobenzene is
nucleophilic substitution reactions. smaller than C-X bond length in
Delhi 2015 CH-X. AllIndia2013
. Delhi 205 46. Explain the following:
42.) ) Why are alkyl halides insoluble in (i) The dipole moment of chlorobenzene
water?
is lower than that of cyclohexyl
(i) Why is butan-1-ol optically inactive chloride.
but butan-2-ol is optically active?
ht i) Alkyl halides, though polar, are
(ii) Although chlorine is an electron immiscible with water.
withdrawing group, yet it is
(ii) Grignard reagents should be
ortho, para- directing in electrophilic
prepared under anhydrous
aromatic substitution reactions. conditions. Delhi2013
Why? Foreign 2015 47. Although, chlorine is an electron
43. () Draw the structures of major
monohalo products in each of the
withdrawing group, yet it is
ortho, para-directing in electrophilic
lhi2015 following reactions:
aromatic substitution reactions. Explain,
CHOHPC why is it so? Delhi 2012
benzen (a)
48. Answer the following questions:
engthi
(b) CH2-CH= CH2 )What is meant by chirality of a
+ HBr- compound? Give an example.
benzent

xyl