15 ALKYNES

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15.1 Introduction : iv) Side chains if present are located by proper
Q.1.What are alkynes ? numbers.

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Ans : Alkynes are aliphatic unsaturated Compound Derived name IUPAC name
hydrocarbons containing a carbon-carbon
CH ≡ CH Acetylene Ethyne

.
triple bond (C ≡ C) in their molecules.

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H3C __ C ≡ CH Methyl acetylene Propyne
e.g. CH ≡CH Acetylene
_
CH3 C ≡ CH Propyne. H3C __ CH2 __ C ≡CH Ethyl acetylene But-1-yne

sp
a) General formula of alkynes is CnH2n-2. CH3 __ C ≡ C __ CH3 Dimethyl acetylene But-2-yne
b) Alkynes contain four hydrogen atoms less than CH3 __ C ≡ C __ C2H5 Ethyl methyl acetylene Pent-2-yne
corrosponding alkanes & two hydrogen aoms less

log
H3C __ CH__ C ≡CH Isopropyl acetylene 3-Methyl-
than corrosponding alkenes. |
CH3 but-1-yne
c) The first member of alkynes is acetylene hence

.b
they are called acetylenes. Q.3. Give the IUPAC names of the following
d) The _ C ≡C _ (functional group in alkynes) is called compounds.
acetylenic linkage or bond.
–––––––––––––––––––––––––––––––––––––– s
Compounds
i) CH3__CH2__CH__C ≡CH
IUPAC names
3 Methylpent-1-yne
es
|
15.2 Electronic structure of acetylene CH3
Q.2. Give dash and dot ( structures) formulae
ii) CH3__C ≡C __ CH__ CH3 4-Methylpent_2_yne
cc

of i) Acetylene ii) Propylene |

Ans: i) Acetylene CH3
––––––––––––––––––––––––––––––––––––––
H x • C :: C • x H
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H ______ C ≡≡≡ C ______ H 15.4 General methods of preparation

:

Structural formula Electronic formula

of alkynes
ii) Propylene i) By dehydrohalogenation of dihalides
to

Hx
. ii) From calcium carbide
CH3 ___ C ≡ C ___ H Hx C C C x H
.. .. ..
.

iii) From tetrahalides using Zn ( dehalogenation)

.
..

.x
re

H i) By dehydrohalogenation of dihalides :
(Dash strucutre ) ( Dot structure ) Dihaloalkanes :
The derivatives of alkanes obtained by
a

( Lewis electron-dot formula )

–––––––––––––––––––––––––––––––––––––– replacing two H atoms by two halogen atoms
sd

15.3 Nomenclature of alkynes are called dihaloalkanes.

a) Derived names : The first member of alkyne series They are of two types :
is acetylene.Other members are considered as i) Geminal dihalides ii) Vicinal dihalides
aim

alkyl derivatives of acetylene, obtained by i) Geminal dihalides : The dihalides in which

replacing one or both H __ atoms by alkyl groups. both the halogen atoms ( X-atoms) are attached
to the same carbon are called as geminal
b) IUPAC names : (Rules)
dihalides.
w.

i) Select the longest continuous carbon chain

Their common name is alkylidene dihalide
containing triple bond as the parent alkane.
e.g.
ii) From the name of parent alkane suffix _ane is Cl
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i) CH2Cl2 ii) CH3__ CH

replaced by _yne (i.e. alkane → alkyne).
Cl
iii) Indicate the position of triple bond by lowest Methylene dichloride Ethylidene dichloride.
possible number. (Dichloromethane) (1,1__ Dichloroethane.)

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 DISHA SCIENCE ACADEMY
i) The apparatus is flushed with N2 gas to displace
Br
iv) CH3 C CH3
__ __
iii) CH3 CH2 CH
__ __
air since acetylene forms explosive mixture with
Br Cl Cl oxygen in air.

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n-Propylidene dibromide Isopropylidene dichloride. ii) Pieces (lumps) of calcium carbide are taken in a

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(1,1 - Dibromopropane) (2,2 - Dichloropropane) conical flask fitted with a dropping funnel and a
delivery tube.
ii) Vicinal dihalides : The dihalides in which the
iii) Water is then added dropwise on calcium carbide

.
two halogen atoms are attached to adjacent
from dropping funnel, when acetylene gas is

ot
carbon atoms are called vicinal dihalides.
obtained.
Their common name is alkylene dihalide iv) Acetylene contains impurities of hydrogen

sp
e.g. i) CH2 __ CH2 ii) CH3__ CH __
CH2 sulphide, phosphine (PH3), ammonia etc. It is
purified by passing through acidified CuSO4
Cl Cl Cl Cl

log
Ethylene dichloride Propylene dichloride. solution.
(1,2 __ Dichloroethane.) ( 1,2 __ Dichloropropane.)
v) Pure acetylene is then collected by downward
displacement of water.
Q.4. What is action of alcoholic KOH on

.b
i) Ethylidene dichloride
Dropping Acetylene
ii) Propylene dibromide. funnel __ (Pure)

Ans : i) When ethylidene dichloride is boiled with s Water __

Impure C2H2
es
→
alcoholic caustic potash acetylene is obtained.
Acidified Water
Cl CuSO4
cc

CH2 C H + 2KOH∆→ CH ≡ CH + 2KCl + 2H2O

__ __

Cl Alcoholic Ethyne Calcium

∆→carbide
Ethylidene dichloride
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ii) When propylene dibromide is boiled with alcoholic Fig. 15.1 Preparation of Acetylene.
––––––––––––––––––––––––––––––––––––––
caustic potash propyne is obtained.
iii) From tetrahalides using Zn ( dehalogenation) :
to

CH3__CH __
CH 2 +2KOH CH3_C≡CH +2KBr
Propyne
Q.7.How will you prepare acetylene from
Br Br Alcoholic +2H2O
re

Propylene dibromide
ethylene tetrabromide.
–––––––––––––––––––––––––––––––––––––– Ans : When ethylene tetra bromide reacts with zinc
ii) From calcium carbide :
a

in presence of methyl alcohol to form acetylene

Q.5.How will you prepare acetylene ( ethyne )
Br Br
sd

by calcium carbide.
∆
Ans : When calcium carbide reacts with water to H – C – C– H + 2.Zn  → H-C≡C-H + 2 ZnBr2
Methanol
Acetylene
form acetylene. Br Br
aim

C ≡ C + 2HOH CH ≡ CH + Ca(OH)2
(1,1,2,2- tetrabromoethane)
Ca Acetylene Calcium carbide ––––––––––––––––––––––––––––––––––––––
–––––––––––––––––––––––––––––––––––––– 15.5 Chemical Properties of Acetylene
w.

Q.6. Explain the preparation of acetylene in i) Alkynes are highly unsaturated compounds.
laboratory. They contain a triple bond which consists of one
Ans : In laboratory acetylene is prepared by the action sigma (σ) and two pi (π) bonds.
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of water on calcium carbide. ii) Hence characteristics reactions of alkynes are

C ≡ C + 2HOH CH ≡ CH + Ca(OH)2 addition reactions ( similar to alkenes ).
Ca Acetylene Calcium carbide iii) Addition reactions of acetylene occurs in two steps.

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 DISHA SCIENCE ACADEMY
In first step, one molecule of reagent is added to Br H
form ethylene derivatives. This on addition of CH ≡ CH + Br2 C=C Br→
2

Acetylene aq. H Br

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second molecule of reagent in second step gives
trans-1,2 Dibromoethene
ethane derivative.

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iv) Chemical properties of acetylene : Br Br

1) Hydrogenation 2) Halogenation H__ C __

C __
H

.
Br Br
3) Hydrohalogenation 4) Addition of H2SO4

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(1,1,2,2-terabromoethane)
5) Addition of H2O 6) Ozonolysis ––––––––––––––––––––––––––––––––––––––
7) Formation of benzene 3) Hydrohalogenation :

sp
–––––––––––––––––––––––––––––––––––––– Q. 11. Explain Hydrohalogenation of acetylene.
1) Hydrogenation : Addition of hydrogen Ans : Addition of halogen acid ( HX )

log
Q.8.Explain the addition of hydrogen on acetylene. Acetylene combines with two molecules of
OR halogen acid to form first vinyl halide and then
What is the action of hydrogen on acetylene? ethylidene dihalide.

.b
Ans : When acetylene upon catalytic hydrogenation Addition of second HX molecule takes place
gives ethane. according to Markownikoff's rule. Reactivity of

CH ≡ CH + H2
Ni
CH2 = CH2
sthe acids is HI > HBr > HCl.
es
523 - 573 K CH ≡ CH + H-Br → CH = CH HBr
Acetylene Ethylene 2
Acetylene
| (Markownikoff's addn)
Ni Br
cc

CH2 = CH2 +H2 CH3 – CH3

523 - 573 K Vinyl bromide
Ethylene Ethane Br
––––––––––––––––––––––––––––––––––––––
CH3 – CH
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2) Halogenation : Addition of halogens

Br
Q.9.What is the action of chlorine on acetylene? Ethylidene dibromide
to

Ans : When acetylene combines with chlorine in the

HI
presence of carbon tetrachloride to form ethylene CH ≡ CH + H-I → CH = CH
2
| (Markownikoff's addn)
re

tetrachloride. Acetylene
I
Cl H Vinyl iodide I
CH ≡ CH + Cl2 
→ Light C=C Cl→ CH3 – CH
a

Acetylene H Cl I
sd

Acetylene dichloride
Ethylidene iodide
( trans-1,2-Dichloroethane)
Cl Cl CH2 = CH – group is called vinyl group.
aim

H C
__ __
C __
H ––––––––––––––––––––––––––––––––––––––
Cl Cl Q.12. What is action HBr on acetylene in
Acetylene tetrachloride presence of peroxide.
( 1,1,2, 2-Dichloroethane)
Ans :Peroxide effect : Acetylene reacts with HBr
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–––––––––––––––––––––––––––––––––––––– in presence of peroxide to give antimarkownikoff's

Q.10. What is action of bromine on ethyne
addition product 1,2-dibromoethane.
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Ans : Acetylene combines with bromine water to

HBr
form ethylene tetrabromide. CH ≡ CH + HBr → CH2= CH CH2 __ CH2
| peroxide | |
Acetylene Br Br Br
Vinyl bromide Ethylene dibromide

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 DISHA SCIENCE ACADEMY
N.B. Peroxide effect is observed only in addition of O
CH ≡ CH + O3 Ether
HBr ( and not for HCl or HI ) H – C –––– C – H
Acetylene
Q.13. How will you convert acetylene into O –––– O

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Acetyleneozonide
i) Ethylidene dibromide & O

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ii) Ethylene dibromide. H – C –––– C – H Zn
–––––––––––––––––––––––––––––––––––––– H – C – C – H + H2O2
H2O
4) Addition of concentrated H2SO4 : O –––– O O O
Acetyleneozonide

.
Q.14. Explain addition of concentrated H2SO4 Glyoxal
––––––––––––––––––––––––––––––––––––––

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on ethyne OR How will you convert
7) Formation of benzene ( polymerisation ) :
acctylene into ethylidene dihydrogen
Q.17. Explain the formation of benzene by
sulphate.

sp
acetylation.
Ans : Acetylene combines with two molecules of
Ans : When acetylene is passed through red hot iron
H2SO4 to form first vinyl hydrogen sulphate and

log
then ethylidene dihydrogen sulphate tube at 773K it polymerisation give benzene.
( a Markownikoff's addition product ). HC HC
CH Hot iron tube HC CH
CH ≡ CH + HOSO3H HC
CH2 = CH

.b
Acetylene CH 773 K HC CH
OSO3H HC
Vinyl hydrogen sulphate HC CH
Acetylene ( 3 molecules )
HOSO3H
OSO3H s
Q.18. Give the uses of acetylene :
Benzene
es
CH3 – CH
Markownikoff’s addn
Uses : Acetylene is used .
OSO3 H
Ethylidene dihydrogen sulphide i) In artificial ripening of fruits.
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5) Addition of water : Hydration of Acetylene : ii) As illuminant (i.e. for producing light).
Q.15. Explain the addition of water molecule on iii) In oxyacetylene flame (about 3273 K) used for
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acetylene. cutting and welding metals.

Ans : When acetylene is passed through dil H2SO4 iv) In preparation of acetaldehyde, acetic acid, ethyl
to

(42%) at 333K in presence of mercuric sulphate alcohol etc.

catalyst ( 1% ), acetaldehyde is obtained. v) In preparation of vinyl chloride which is used to
prepare polyvinyl
re

The intermediate product vinyl alcohol

is quite unstable. It isomerises to give chloride plastic (P.V.C.).
acetaldehyde. vi) In preparation of acrylonitrile which is used to
a

dil. H2SO4 prepare synthetic rubber.

CH ≡ CH + HOH CH2 = CH
sd

Acetylene
HgSO4 ( 1%) 333 K
OH
vii) In preparation of acetylene dichloride and
Vinyl alcohol acetylene tetra chloride which are used as
( enol )
solvents.
aim

H
Isomerism
CH3 – C
*******
O
Acetaldehyde
w.

––––––––––––––––––––––––––––––––––––––
6) Ozonolysis: Addition of ozone :
Q.16. Explain the ozonolysis of acetylene.
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Ans : When ozone is passed through the solution of

acetylene in CCl4 ozonide is formed. This upon
hydrolysis by water in presence of zinc gives
glyoxal.

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