18/11/2024

DAY – 1 | CHEMISTRY

HALOALKANES
AND HALOARENES
MARK DISTRIBUTION | Haloalkanes and Haloarenes

Haloalkanes &
MARKS TYPE
Haloarenes (9)
VSA
2 R+H
(1 Mark)
SA
1 U
(2 Mark)
LA
1 R
(5 Mark)
Haloalkanes and Haloarenes-INDEX

MARKS No of Questions

VSA (1 Mark) 10

SA (2 Mark) 25

LA (5 Mark) 5

Most Important Topics Last Slide

 VSA (1 Marks)
Q1) Statement I: Enantiomers are non-
superimposable mirror images on each
other.
Statement II: A racemic mixture shows zero
optical rotation.

Identify the correct statement

a) Both statement I and II are correct
b) Both statement I and II are incorrect
c) Statement I is correct and statement II is
incorrect.
d) Statement I is incorrect and statement II
is correct.
 VSA (1 Marks)

Q2) 1,2-dichloroethane is an example of

a) alkylene dihalides
b) alkylidene halides
c) vicinal dihalides
d) gem-dihalides.
 VSA (1 Marks)
Q3) Four haloalkane compounds
represented by the letters M, N, O and P
having boiling point are 24.2°C,
38°C, 3.56°C and 101.6°C respectively.
Among the four compounds N most
likely to be:

a) CH3Cl
b) CH3Br
c) C2H5Br
d) d) C3H7I
VSA (1 Marks)
Q4. The homologous series of alkyl
halides are represented by general
formula

(a) CnH2n+1X
(b) CnH2nX2
(c) CnH2n-1X3
(d) CnH2n+2X
 VSA (1 Marks)

Q5. Toluene reacts with a halogen in

the presence of iron (III) chloride
giving ortho and para halo
compounds. The reaction is :

A. Electrophilic elimination reaction

B. Electrophilic substitution reaction
C. Free radical addition reaction
D. Nucleophilic substitution
reaction
 VSA (1 Marks)

Q6. Which reagent will you use for the following reaction?
𝑪𝑯𝟑 𝑪𝑯𝟐 𝑪𝑯𝟐 𝑪𝑯𝟑 → 𝑪𝑯𝟑 𝑪𝑯𝟐 𝑪𝑯𝟐 𝑪𝑯𝟐 𝑪𝑰 + 𝑪𝑯𝟑 𝑪𝑯𝟐 CHCI𝑪𝑯𝟑

A. 𝑪𝑰𝟐 /UV light

B. NaCI + 𝑯𝟐 𝑺𝑶𝟒
C. 𝑪𝑰𝟐 gas in dark
D. 𝑪𝑰𝟐 gas in the presence of iron in dark
VSA (1 Marks)
Q7. Arrange the following
compounds in increasing order of
their boiling points.

A. (b) < (a) < (c)

B. (a) < (b) < (c)
C. (c) < (a) < (b)
D. (c) < (b) < (a)
 VSA (1 Marks)

Q8. The position of -Br in the compound in

𝑪𝑯𝟑 𝑪𝑯 = 𝑪𝑯𝑪(𝑩𝒓)(𝑪𝑯𝟑 )𝟐 can be classified
as_____.
A. Allyl
B. Aryl
C. Vinyl
D. Secondary
VSA (1 Marks)

Q9. Chlorobenzene is formed by

reaction of chlorine with benzene
in the presence of AIC𝑰𝟑 . Which of
the following species attacks the
benzene ring in this reaction?
A. 𝑪𝑰−
B. 𝑪𝑰+
C. AIC𝑰𝟑
D. [AIC𝑰𝟒 ]−
VSA (1 Marks)

Q10. What is ‘A’ in the following

reaction?

A. B.

C. D.
MOP Haloalkanes SA (2 Marks)
Q1) Explain Swartz reaction with an
example

Ans) Alkyl fluorides are synthesized by heating an

alkyl chloride/bromide in the presence of a
metallic fluoride such as AgF, Hg2F2,CoF2 or
SbF3.The reaction is termed as Swarts reaction.

Ex:
 SA (2 Marks)
Q2) Explain Finkelstein reaction with
example.

Ans) Alkyl iodides are often prepared by the

reaction of alkyl chlorides/bromides with NaI in
dry acetone. This reaction is known as Finkelstein
Reaction. Ex:
SA (2 Marks)

Q3.How do you prepare alkyl halides

from alcohols?
[2014M,2016J, 2015M]

Ans) The alkyl halides can be prepared from

alcohols by treating with SOCl2. This is a
preferable method as the byproducts produced
are gases.
SA (2 Marks)

Q4. How do you prepare alkyl halides

from alkenes by adding
(i) Hydrogen halides
(ii) Halogen
Give examples
[March 2015]
SA (2 Marks)

Q5. A hydrocarbon C5H10 do not

react with Cl2 in dark but react in
sunlight to give monochloro
compound C5H9Cl. Identify the
hydrocarbon.

Ans) General Formula: CnH2n

Alkene or cyclic structure
• Does not react with dark: cyclic structure
• Monochloro compounds – All H are equivalent
MOP haloarenes SA (2 Marks)
Q6) Give the preparation of aryl halides by
Sandmeyer reaction.

• Aniline reacts with dilute nitrous acid to

form benzene diazonium chloride which
reacts with CuCl or CuBr to give aryl
chloride or aryl bromide. This is Sandmeyer
Reaction.
Physical Properties SA (2 Marks)

Q7. In haloarenes, para-isomers have

higher melting point as compared to their
ortho-and meta-isomers. why?
[2016J]
 SA (2 Marks)

Q8. Arrange in increasing order of boiling

point
(i) bromomethane, bromoform,
chloromethane, dibromomethane

(ii) 1-chloropropane, isopropyl chloride, 1-

chlorobutane
Chemical Reactions (SN2 & SN1) SA (2 Marks)
Q9) Write the steps involved in SN1
mechanism for the conversion of tert-butyl
chloride to tert-butyl alcohols
SA (2 Marks)
Q10) Write the steps involved in SN2
mechanism for the conversion of
chloromethane to methanol.
Chemical Reactions (Stereochemical
Aspects of Nucleophilic Reaction)
SA (2 Marks)

Q11. What is chirality? What is the

condition for chiralty ?
[2016M, 2019M]

Ans) Objects which are non superimposable on

their mirror images are called chiral molecules
and the property arising from them is called
chirality.
It should contain asymmetric C.
SA (2 Marks)

Q12. Butan-2-ol is a chiral molecule

and optically active. Explain

Ans) Butan-2-ol has four different groups

attached to the C and their mirror images are non
superimposable. Hence, it is chiral.

It does contain asymmetric C.

 SA (2 Marks)

Q13. Define Retention. Give a

chemical reaction that proceeds with
retention of configuration.

Ans) Retention is the preservation of the spatial

arrangements of bonds at asymmetric Carbon.
It does contain asymmetric C.
 SA (2 Marks)

Q14. Define Inversion. Give a chemical

reaction that proceeds with inversion
of configuration.
OR
SN2 reactions of optically active
halides are accompanied by
inversion. Explain with an example

Ans) If the product of the reaction has opposite

configuration of that of the reactant during
reaction is called as inversion.
 Chemical Reactions SA (2 Marks)
(Nucleophilic Substitution)

Q15. How does alkyl halides react with

alcoholic AgCN ? Give equation.
KCN [2015J,2020M]
Carboxylic Acids .
AgNO2
KNO2 Ans) Alkyl halides react with AgCN to form
isocyanides.
 SA (2 Marks)

Q16. Haloalkanes react with KCN to

form alkyl cyanides and with AgCN to
form isocyanides. Explain.

KCN is ionic. Both C and N can donate electrons,

but C only donates because C-C Bond is more
stable.
AgCN is covalent in nature and N is free to donate
electron pair forming isocyanide.
 SA (2 Marks)

Q17. Out of CH2=CHCH2Cl and

CH3CH2CH2Cl which is more active
towards SN1 reaction and Why ?

CH2=CHCH2Cl
A stable Carbocation is formed.
 Chemical Reactions SA (2 Marks)
(Elimination Reaction)

Q18. Explain Zaitesv rule with an

example.
[2014J, 2017J,2018M,2019J]

Ans) Acc to Zaitsev rule, during dehydro-

dehalogenation more substituted alkene is
formed.
Chemical Reactions (Haloarenes) SA (2 Marks)

Q19. Electrophilic Substitution reaction occurs

slowly in haloarenes compared to benzene. Give
reason.

Ans) Due to –I effect of halogen atom, haloarene

have some tendency to withdraw electrons from
the benzene ring.
As a result, ring gets deactivated as compared to
benzene and hence electrophilic substitution
reaction occurs slowly.
 SA (2 Marks)

Q20. Aryl halides are less reactive towards

nucleophilic substitution reaction. Give reasons.
[2014M,2015M,2017M,2017J]

Ans)
i) Resonance effect: Due to resonance the C-X
bond has a partial double bond character and
hence it is difficult to substitute it,
ii) Sp2 hybridization of C : Due to the sp2 nature
of C in CX bond it has more s character and
hence holds the bond strongly.
 SA (2 Marks)

Q21. How will you convert chlorobenzene to

phenol by Dow’s process.

Ans) Chlorobenzene on reaction with NaOH at

623 K and 300 atm pressure gives sodium
phenate ion which on acidification gives phenol.
Ex:
 SA (2 Marks)
Q22) (a)Explain Fittig’s reaction
(b) Wurtz Fittig
(c) Fittig
Ans) Aryl halides when treated with sodium
in dry ether, give compounds where two aryl
groups are joined together. It is called Fittig
reaction..
Ex:
SA (2 Marks)
 SA (2 Marks)

Q23. Explain nitration of chlorobenzene.

[2020M]
Halogenation
Sulphonation Ans) Chlorobenzene reacts with conc HNO3 in
Friedel Craft presence of Conc. H2SO4 to give ortho & para
nitrochloro benzene
Reaction
Ex:
SA (2 Marks)
 Chemical Reactions SA (2 Marks)
(Reaction with Metals)
Q24) What are Grignard reagents? Write its
general formula.

Ans) Organomagnesium halides are called as

Grignard reagents.
Polyhalogen Compounds SA (2 Marks)
Q25) What are freons? Name the poisonous
gas evolved when Cl2 is oxidized by air.

Ans) The chlorofluorocarbon compounds of

methane and ethane are collectively
known as freons.
Phosgene (COCl2)
 SA (2 Marks)

Q.26. Chlorofrom is stored in closed dark

coloured bottles. Why?
[2022A]

Ans)CHCl3 is slowly oxidized by air in the

presence of light to a poisonous gas COCl2, also
known as phosgene.

2CHCl3 + O2 →2COCl2 + 2HCl

LA (5 Marks)
Q1) (a) Complete the following equation:

(b) Explain Saytzeff rule with an example.

LA (5 Marks)
Q2) (a)Write any three differences
between SN1 and SN2 reaction
mechanisms.

b) Identify A and B in the given

reaction
LA (5 Marks)

Q3) (a) Write the mechanism involved in

the conversion of 2-bromo-2-
methylpropane to 2-methylpropan-2-ol.

b)What are enantiomers? Name one

physical property which differs
enantiomers.
LA (5 Marks)
Q4) (a) Write the equations for the
steps involved in the SN1 mechanism
of hydrolysis of 2-bromo 2-methyl
propane.

b) (i) Name the product formed for the

reaction of isopropyl iodide on
alcoholic KОН.
(ii)What is the condition to be satisfied
for a compound to be chiral?

c) What is racemic mixture?

c) Equimolar mixture of dextrorotatory and

laevorotatory isomers is called racemic mixture.
LA (5 Marks)
Q5) Primary alkyl halide C4H9Br (A)
reacted with alcoholic KOH to give
compound (B). Compound (B) is
reacted with HBr to give (C) which is
an isomer of (A). When (A) is reacted
with sodium metal it gives compound
(D), C8H18 which is different from the
compound formed when n - butyl
bromide is reacted with sodium. Give
the structural formula of (A) and write
the equations for all the reactions.
 Most important Topics

NAME
DEFINITIONS MECHANISM
REACTIONS
Retention Swarts SN1
Inversion Finkelstein SN2
Stereocenter Dow process
Enantiomers Friedel Craft
Racemic mixture Wurtz
Fittig
Wurtz Fittig
Sandmeyer