10 Halogen Derivatives of Chapter

Alkanes 10: Halogen Derivatives of Alkanes

and Arenes

and Arenes

1. CH3 – CH2 – CH2 – Br 

Alc.KOH
 CH3 – CH = CH2 
HBr
 CH3 – CH – CH3
1-Bromopropane Propene
(A) Br
2-Bromopropane
(B)

aq.KOH
CH3 – CH – CH3

OH
Propan-2-ol

Br2
2. CH3 – CH2 – CH2 – I 
Alc.KOH
 CH3 – CH = CH2   CH3 – CH – CH2
Propene
1-Iodopropane
(A) Br Br
1,2-Dibromopropane
(B)

NaNH2/NH3
CH3 – C  CH
Propyne
(C)
CH3
1 2 3 4 5
3. CH3 – C  C Na+ + (CH3)2CHCl 
Alcohol
CH 3  C  C  CH  CH 3 + NaCl
Sodium methyl 2-Chloropropane
4-Methylpent-2-yne
acetylide

4. Order of reactivity towards nucleophilic substitution reaction is:

Allyl halide > alkyl halide > vinyl halide > halo benzene

5. CH3 2
CH – Cl
CH3
Isopropyl chloride

Secondary alkyl halide can undergo hydrolysis either by SN1 or SN2 mechanism.

6. H It undergoes SN1 mechanism and due to asymmetric carbon atom, it is optically active.

C
Br CH3
C6H5
1-Bromo-1-phenylethane

7. Due to resonance stabilisation in aryl halides, C – X bond acquires some double bond character.

8. Presence of electron withdrawing group (NO2) facilitates the benzene ring towards nucleophilic substitution
reaction.

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Std. XII : Triumph Chemistry
9. CH3 CH3
COOH COOH
+ Br2  Fe

o-Toluic acid
Br
3-Bromo-6-methylbenzoic acid

10. CH2  Cl CH2CN

C2 H5  OH
+ NaCN  

Br Br
4-Bromo benzyl 4-Bromo benzyl
chloride cyanide

NH2 N2Cl Br
11.
NaNO2  HCl

280 K
 
CuBr / HBr
Sandmeyers
 + N2
reaction
Benzene Bromobenzene
Aniline
diazonium
chloride
12. Due to o- and p-directing  Cl group, all the products given in the option (A), (B) and (C) will be formed.

Cl Cl
Cl Cl
13. + 10Cl2  hv
Cl Cl + 10HCl

Cyclopentane
Cl Cl
Cl Cl
1,1,2,2,3,3,4,4,5,5-Decachlorocyclopentane
2
14. CH3 – CH – CH2 – CH3 (2-Chlorobutane) optically active compound undergoes SN mechanism with
|
Cl
100% inversion.

15.

3 + CHCl3 
anhydrous AlCl3
 C–H + 3HCl

Benzene Chloroform

Triphenylmethane
(Friedel Craft’s Reaction)

   
H I I
16. CH3 – CH = CH2 
peroxide
 CH 3  CH  CH 3 
peroxide
 CH3 – CH – CH3
Propene |
I
2-Iodopropane

17. Primary alkyl halides undergo SN2 reaction which involves the complete stereochemical inversion.
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 Chapter 10: Halogen Derivatives of Alkanes
and Arenes
18. CH3 CH3 CH3

 CH3 – CH2 – C = CH2 

H2 / Catalyst
CH3 – CH2  CH – CH2Cl 
C2 H5 ONa / C 2 H5 OH
peroxide
CH3 – CH2 – CH – CH3
1-Chloro-2-methylbutane 2-Methylbutane

H3O  Br
19. C6H5CH2Br 
Mg, ether
 C6H5CH2MgBr   C6H5CH3 + Mg
Benzyl Benzyl Toluene OH
bromide magnesium
bromide
C2H5 C2H5
20. 2CH3(CH2)2  CH – CH2CH3 + 2Na 
Wurtz reaction
 CH3(CH2)2 – CH  CH  (CH2)2CH3 + 2NaI

I 4,5-Diethyloctane
3-Iodohexane

21. Freon (CCl2F2), teflon [ (CF2  CF2 )n] and iodoform (CHI3) are halogen derivatives of alkane.
Vinyl chloride (CH2 = CH  Cl) is not a haloalkane.