Haloalkanes & Haloarenes
Haloalkanes & Haloarenes
Haloalkanes & Haloarenes
CBSE 2024
Haloalkanes &
Haloarenes
APNI KAKSHA NOTES
APNI KAKSHA 1
Haloalkanes
Haloalkanes are the halogen deivatives of hydrocarbons.
Classification of Haloalkanes
Monohalides (R-X): Monohalides are monohalogen
derivatives of alkanes which have a general formula
CnH2n+1X and are known as alkyl halides.
R-X may be of three types:
1 Primary R − CH X
2 Secondary R CHX
3 Tertiary R CX
Dihalides (𝐂 𝐇 𝐗 ) : Dihalides are the di-halogen derivatives of alkanes and are of geminal and
vicinal types.
Example
(a) CH CHBr (Ethylidine dibromide),
(b) BrCH CH Br (Ethylene dibromide)
(a) Mono Halogen Derivatives Examples
Example
(i) Chlorobenzene (ii) p-Bromotoluene
APNI KAKSHA 2
Example
(i) 3-Haloprop-1-ene(1º) (ii) 3-Halo-3-methylcyclohex-1-ene(3)
Which of the following belongs to the class of Vinyl halides? CBSE 2023
(A) CH2 = CHCH2CH2Cl (B) CH2 C CH3
|
Br
(C) CH2 = CH – CH2 – Br (D) CH C — Br
Named Reaction
(a) Sandmeyer Reaction:
+ 2Na+R– X +2Nax
APNI KAKSHA 3
(f) Fitting Reaction:
Methods of preparation
Halogenation of alkanes
R H X 2
hv
R X HX
For example
CH4 Cl2 hv
or520650K
CH3Cl CH2Cl2 CHCl3 CCl4
Cl2 ,hv
CH3 CH2 CH3
298K
CH3 CH2 CH2 Cl CH3 CHCl CH3
Propane 1Chloropropane(45%) 2Chloropropane55%
Cl2 ,hv
CH3CH2CH2CH3
298K
CH3CH2CH2CH2Cl CH3CH2 CHCl CH3
Butane 1Chlorobutane 28% 2Chlorobutane72%
5𝐻𝐼 + 𝐻𝐼𝑂 ⎯ 3𝐼 + 3𝐻 𝑂
APNI KAKSHA 4
MIND MAPS
APNI KAKSHA 5
In general: CH X > C H X > C H X > C H X
Q. Haloalkanes are less soluble in water, why?
Ans. Haloalkanes are polar molecules, neither they form H-bond with water nor can they break
the H-bonds already existing between water molecules. As a result, the solubility of
haloalkanes in water in very low.
CHEMICAL REACTIONS
Fast
Slow
Fast
In the following pairs of halogen compounds, which would undergo S N2 reaction faster?
APNI KAKSHA 6
As iodine is a better leaving group because of its large size, it will be
released at a faster rate in the presence of incoming nucleophile.
Predict the order of reactivity of the following
Compound in SN1 and SN2 reaction.
(i) The four isomeric bromobutanes
(ii) C6H5CH2Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br, C6H5C(CH3)(C6H5)Br
Fast
Slow
Here, nucleophile attacks from the opposite direction of the leaving group. Thus, SN2
reaction always leads to an inversion of stereochemistry. This reaction works best with
methyl and primary halides because bulky alkyl groups block the backside attack of the
nucleophile. In addition, the stability of the leaving group as an anion and the strength of
its bond to the carbon atom both affect the rate of reaction.
APNI KAKSHA 7
Electrophilic Substitution Reaction of Haloarenes:
APNI KAKSHA 8
Previous year Questions
Q.1 (a) Write equation for preparation of 1-iodobutane from 1-chlorobutane. [CBSE 2022]
(b) Out of 2-bromopentane, 2-bromo-2-methylbutane and 1 -bromopentane, which
compound is most reactive towards elimination reaction and why?
(c) Give IUPAC name of
(b) Write the structure of the product when chlorobenzene is treated with methyl
chloride in the presence of sodium metal and dry ether
(c) Write the structure of the alkene formed by dehydrohalogenation of 1-bromo-1
methylcyclohexane with alcoholic KOH.
Ans. (A) (i)
4. Out of Chlorobenzene and Cyclohexyl chloride, which one is more reactive towards
nucleophilic substitution reaction and why? [CBSE 2019]
Ans. Cyclohexyl chloride
5. Among all the isomers of molecular formula C HBr, identify [CBSE 2019]
(a) The one isomer which is optically active.
(b) The one isomer which is highly reactive towards SN2.
(c) The two isomers which give same product on dehydrohalogenation with alcoholic
KOH.
Ans. (a) (b) CH3CH2CH2CH2Br
APNI KAKSHA 9
(ii) 1-bromo-2-methylpropane
APNI KAKSHA 10