HALOALKANES &HALOARENES

WORK SHEET -1
A.Write the IUPAC name for the following compounds
1

10 CH3CH=CHC(Br)(CH3)2
11 p-ClC6H4CH2CH(CH3)2
12 m-ClCH2C6H4CH2C(CH3)3
13 o-Br-C6H4CH(CH3)CH2CH3
14 ClCH2C≡CCH2Br
15 (CCl3)3CCl
16 CH3C(p-ClC6H4)2CH(Br)CH3
17 (CH3)3CCH=CClC6H4I-p

18.
B. Write the structure
1. 2-(2-bromophenyl)butane

2. 2-(2-chlorophenyl)-1-iodooctane

3. 1-Bromo-4-sec-butyl-2-methylbenzene

4. 3-(4-chlorophenyl)-2-methylpropane.

5. 4-tert-Butyl-3-iodoheptane

c. write the Reagents

QUESTION REAGENT 13. Benzene diazonium REAGENT
chloride to iodobenzene
1. CH3Br to CH3 CN 14. Chlorobenzne to tolune
2. CH3Br to CH3 NC 15. Benzene diazonium
chloride to chlorobenzene
3. CH3Br to CH3 OH 16. Chlorobenzne to phenol
4. CH3Br to CH3 NO2 17. Chlorobenzne to 4-chloro
acetopheenone
5. CH3Br to CH3 ONO 18, Chloroethane to ethene
6. CH3Br to CH3 O C2H5 19. Ethanol to idoethane
7. Tolune to benzyl chloride 20. Cyclohexanol to
chlorocyclohexane
8. Chloro benzene to biphenyl 21. Bromoethane to butane
9. Propene to 1-bromopropane 22. CH3MgBr to CH3D
10. Ethane to chlro ethane 23. Chloro ethane to butyne
11. Chloro ethane to iodoethane 24. Bromoethane to butane
12. Bromo ethane to floroethane

HALOALKANES &HALOARENES
 WORK SHEET -2

Identify the name of reaction and write the chemical equation

1. Chlor/bromoalkanes reacts with sodium iodide in dry acetone forms iodoalkanes

2. Chlor/bromoalkanes reacts with metal fluoride forms floroalkanes

3, Benzene diazonium chloride reacts with cuprous chloride dissolved in hydrochloric acid
forms chlorobenzene by replacing diaonium group by chloride ion

4. Chloro ethane with alcKOH forms ethene

5. Chloro ethane with sodium in dry ether forms butane

6. Arylhalide + alkyl halide + sodium gives alkyl arenes

7. Arylhalide + sodium gives bi phenyl

8. Aniline with nitrous acid form benzne diazonium chloride

Convert the following

1. How will you bring about the following conversions?

(i) Ethanol to but-1-yne (SoCl2, Sodium ethaniyde)

(ii) Ethane to bromoethene ( chlorine /U.V light)

(iii) Propene to 1-nitropropane (HBr/peroxide, AgNO2)

(iv) Toluene to benzyl alcohol( chlorine /U.V light,NaOH)

(v) Propene to propyne (Br2, alc KOH, alc KOH)

(vi) Ethanol to ethyl fluoride (SoCl2,AgF)

(vii) Bromomethane to propanone (WILL STUDY IN CABONYL COMPOUNDS )

(viii) But-1-ene to but-2-ene (HBr,alc KOH)

(ix) 1-Chlorobutane to n-octane (Na in dry ether)

(x) Benzene to biphenyl.(Cl2/Fe, Na in dry ether)

HALOALKANES &HALOARENES
 WORK SHEET -3

1. Give the uses of freon 12, DDT, carbon tetrachloride and iodoform

2. How the following conversions can be carried out?

a) Propene to propan-1-ol(HBr/peroxide,aq KOH)

b) 1-Bromopropane to 2-bromopropane(alc KOH,HBr)

c) Benzene to 4-bromonitrobenzene(Br 2/Fe, con HNO3/con H2SO4)

d) Ethanol to propanenitrile ( SoCl2,KCN)

e) Aniline to chlorobenzene(HNO2, CuCl/HCl)

f) 2-Chlorobutane to 3, 4-dimethylhexane( Nain dry ether)

g) 2-Methyl-1-propene to 2-chloro-2-methylpropane (HCl)

3. Write the mechanism of the following reaction:

4. Write a chemical test to distinguish between
a)chlorobenzene and benzyl chloride

b)vinyl chloride and tert-butyl chloride

c.2-bromo butane and 2-iodo butane

5. Which of the following give major product when it reacts with alc KOH?Why?
1-Bromobutane , 2-Bromobutane

Reasoning questions
1. sulphuric acid not used during the
reaction of alcohols with KI
2. Thionoyl chloride is preferred to make
chloroalkanes from alochols
chiral molecule in the following pair

CH3Br is treated with KCN forms cyanide

but with AgCN froms isocyanide
following pair undergoes faster SN1
reaction

React faster in SN2 displacement

1-Bromopentane or 2-Bromopentane
Out of SN1 and SN2, which occurs with
a) inversion of configuration
b)racemisation
Chlorobenzene is less reactive towards a
nucleophilic substitution reaction
Alkyl halides though polar are immiscible
in water.
Grignard reagent should be prepared
under anhydrous conditions
Alkyl halides miscible in organic solvent
Which of the following would you expect
to react faster by SN2 mechanism and
why?

Which out of the following reacts faster

by SN1 mechanism and why?

Which of the following would you expect

to react faster by SN2 mechanism with –
OH and why?
CH3Br or CH3I
The dipole moment of chlorobenzene is
lower than that of cyclohexylchloride
p-Dichlorobenzene has higher M.P. than
those of o-and m-isomers
The treatment of alkyl chloride with
aquous KOH leads to the formation of
alcohol but in the presence of alcoholic
KOH,alkene is the major product.
A solution of KOH hydrolyses
CH3CHClCH2CH3 benzyl chloride and
chlorobenzene one of these is more
easily Hydrolysed?
The C-Cl bond length in chlorobenzene is
less than that in CH3Cl
Chloroform is stored in closed dark color
bottles
The order of reactivity of haloalkanes is
RI>RBr>RCl
Neopentyl chloride ,(CH3)3C-CH3Cl does
not follow SN2 mechanism
Although chlorine is an electron
withdrawing group,yet it is ortho,para
directing in electrophilic
aromatic substitution reaction.Explain
why?
+/- 2-chlobutane is optically active
B.P order RI>RBr>RCl
 B.P of chloroform > chlromethane
B.P of n-chlorobutabe >
isochlorobutane
B,P of haloalkanes> alkanes
Vinyl chloride is less reactive than benzyl
chloride towards nucleophilic
substitution
1-bromo butane is optically inactive and
achiral

Convert
How will you bring about the following conversions?

(i) Ethanol to but-1-yne (SoCl2, Sodium ethaniyde)

(ii) Ethane to bromoethene ( chlorine /U.V light)

(iii) Propene to 1-nitropropane (HBr/peroxide, AgNO2)

(iv) Toluene to benzyl alcohol( chlorine /U.V light,NaOH)

(v) Propene to propyne (Br2, alc KOH, alc KOH)

(vi) Ethanol to ethyl fluoride (SoCl2,AgF)

(vii) Bromomethane to propanone (WILL STUDY IN CABONYL COMPOUNDS )

(viii) But-1-ene to but-2-ene (HBr,alc KOH)

(ix) 1-Chlorobutane to n-octane (Na in dry ether)

(x) Benzene to biphenyl.(Cl2/Fe, Na in dry ether)

Give the uses of freon 12, DDT, carbon tetrachloride and iodoform
How the following conversions can be carried out?

Propene to propan-1-ol(HBr/peroxide,aq KOH)

 1-Bromopropane to 2-bromopropane(alc KOH,HBr)

Benzene to 4-bromonitrobenzene(Br 2/Fe, con HNO3/con H2SO4)

Ethanol to propanenitrile ( SoCl2,KCN)

Aniline to chlorobenzene(HNO2, CuCl/HCl)

2-Chlorobutane to 3, 4-dimethylhexane( Nain dry ether)

2-Methyl-1-propene to 2-chloro-2-methylpropane (HCl)

Write the mechanism of the following reaction:

Complete the reaction

Write chemical equation when
i)ethyl chloride is treated with aquous KOH
ii)chlorobenzene is treated with CH3COCl in the presernce of anhy.AlCl3.

Write a chemical test to distinguish between

a)chlorobenzene and benzyl chloride
b)Chloroform and carbon tetrachloride
Identify A, B, C, D, E, R and R1 in the following:

A hydrocarbon C5H10 does not react with chlorine in dark but gives a single monochloro
compound C5H9Cl in bright sunlight. Identify the hydrocarbon
Among the isomeric alkanes of molecular formula C5H12, identify the one that on
photochemical chlorination yields

(i) A single monochloride.

(ii) Three isomeric monochlorides.

 Write the lower B.P isomers of the compound having formula C4H9Br
----------------------------------- are nucleophiles having two nucleophilic sites. Thus these

Predict all the alkenes that would be formed by dehydrohalogenation of the following
halides with sodium ethoxide in ethanol and identify the major alkene:

(i) 1-Bromo-1-methylcyclohexane
Write the structure of the major organic product in each of the following reactions:

(i)

(ii)

(iii)

(iv)

(v)

(vi)

(vii)

(viii)

Among the isomeric alkanes of molecular formula C5H12, identify the one that on
photochemical chlorination yields

(i) A single monochloride.

(ii) Three isomeric monochlorides.