11th

Organic Chemistry
Alkynes: Preparation
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Can You Crack it
Assertion : Addition of HBr to propene yields 2-bromopropane but in
presence of a peroxide it yields 1-bromopropane.
Reason : When reaction is carried out in the presence of a peroxide it
follows free radical mechanism, 2° free radical is more stable than 1° free
radical.

(a) If both assertion and reason are true and reason is the correct
explanation of assertion.
(b) If both assertion and reason are true but reason is not the correct
explanation of assertion.
(c) If assertion is true but reason is false.
(d) If both assertion and reason are false.
Can You Crack it
Assertion : Decolourisation of KMnO4 solution is used as a test for
unsaturation.
Reason : Alkenes on reaction with cold, dilute aqueous solution of
potassium permanganate produce colorless vicinal glycols.

(a) If both assertion and reason are true and reason is the correct
explanation of assertion.
(b) If both assertion and reason are true but reason is not the correct
explanation of assertion.
(c) If assertion is true but reason is false.
(d) If both assertion and reason are false.
 ALKYNES

Alkynes are aliphatic unsaturated hydrocarbons.

PREPARATION OF ALKYNES

1. From calcium carbide :

CaCO3 -------------> CaO + CO2

CaO + 3C -------------> CaC2 + CO

Calcium
carbide

CaC2 + 2H2O ------------> Ca(OH)2 + C2H

PREPARATION OF ALKYNES

2. From vicinal dihalides.

CH2Br Heat CH
| + 2KOH (alc) ----------------> III + 2KBr + 2H2O
CH2Br CH
Ethylene Acetylene
dibromide
 PHYSICAL PROPERTIES OF ALKYNES

1. Physical State
The first three alkynes are gases while those containing five to
thirteen carbon atoms are liquids and higher alkynes are solids.

2. Melting and Boiling Points

The melting and boiling points of alkynes are quite low and increase
regularly with increase in molecular mass. Alkynes are less volatile
than alkanes and alkenes.
PHYSICAL PROPERTIES OF ALKYNES

3. Solubility
Alkynes are insoluble in water but are soluble in organic solvents
such as benzene, hexane, ether, carbon tetrachloride, etc.

4. Density
All alkynes are lighter than water. Their densities increase regularly
with increase in molecular mass.
CHEMICAL PROPERTIES OF ALKYNES

1. ACIDIC CHARACTER OF ALKYNES

Terminal alkynes (1-alkynes) behave as very weak acids. They react with
strong bases like NaNH2 to form acetylides.
– +
HC ≡ CH + NaNH2 -------> HC ≡ CNa + NH3
Monosodium ethynide
CHEMICAL PROPERTIES OF ALKYNES

1-Alkynes also react with sodium metal to produce hydrogen gas.

– +
HC ≡ CH + Na -------> HC ≡ CNa + ½ H2
Ethyne Sodium ethynide
– – –
HC ≡ CNa+ + Na -------> Na+ C ≡ CNa + ½ H2
Disodium ethynide
CHEMICAL PROPERTIES OF ALKYNES

Explanation of acidic character of terminal alkynes.

The acidic character of terminal alkynes can be explained in terms of sp-

hybrid state of the carbon atom.
d- d+
R—C ≡ C.........H
Can You Crack it
1. The most acidic hydrogen atoms are present in
(a) ethane (b) ethene
(c) ethyne (d) benzene.
Can You Crack it
2. Which of the following alkynes is most acidic?
(a) CH3C ≡ CH (b) CH3C ≡ CCH3
(c) CH3CH2C ≡ CH (d) CH ≡ CH
CHEMICAL PROPERTIES OF ALKYNES

2. ADDITION REACTIONS OF ALKYNES

Some important addition reactions of alkynes are :
1. Addition of dihydrogen,
2. Electrophilic addition reactions,
3. Nucleophilic addition reactions.
ADDITION REACTIONS

1. Addition of Dihydrogen of Alkynes

Alkynes react readily with dihydrogen in the presence of finely-divided
nickel, platinum or palladium as catalysts. The process is known as
catalytic hydrogenation.
Catalyst Catalyst
HC ≡ CH + H2 --------------> CH2 = CH2 ---------------->CH3 – CH3
Ethyne Ethene + H2 Ethane
ADDITION REACTIONS
ADDITION REACTIONS
2. Electrophilic Addition Reactions of Alkynes
(a) Addition of Halogens. Halogens, especially chlorine and bromine add on
alkynes readily producing tetra-halogen derivative. The reaction is carried
out in inert solvent like CCl4.

CCl4
HC ≡ CH + Br2 ------------> BrCH = CHBr
Ethyne 1, 2-Dichloroethene

CCl4
HC ≡ CH + 2Br2 ---------------> Br2CHCHBr2
1, 1, 2, 2-Tetrachloroethane
ADDITION REACTIONS
(b) Addition of Hydrogen halides (HX). In alkynes two molecules of
hydrogen halides (HCl, HBr, HI) add across triple bond to form gem
dihalides as products.
Br
|
CH ≡ CH + HBr ----------> CH2 = CHBr --------------> CH3 – CH – Br
Ethyne Bromoethene M.Rule 1, 1-Dibromoethane
(Vinyl bromide)

Br
+HBr |
CH3C ≡ CH + HBr -------> CH3 – C = CH2 ----------> CH3 – C – CH3
| |
Br Br
Propyne 2-Bromopropene 2, 2-Dibromopropane
ADDITION REACTIONS

3. Nucleophilic Addition Reactions of Alkynes

(a) Addition of Water (Hydration). Alkynes undergo hydration in the presence
of 60% H2SO4 and mercuric ions as catalyst at about 330 K. The products
are carbonyl compounds. In case of ethyne, ethanal is produced. The
initially formed vinyl alcohol is unstable and rearranges (tautomerises) to
more stable ethanal.
Hg2+/H+ Rearrangement
HC ≡ CH + H2O -------------------> H2C = CHOH ----------------------->CH3CHO
330 K <-------------
Acetylene Vinyl alcohol Ethanal
ADDITION REACTIONS
 III. POLYMERISATION IN ALKYNES

1. Cyclic Polymerisation
When acetylene is passed through red hot tube of iron or quartz it
trimerises to form benzene

This is the best route for entering from aliphatic to aromatic compounds.
POLYMERISATION IN ALKYNES
POLYMERISATION IN ALKYNES

2. Linear Polymerisation
Linear polymerisation of ethyne, under suitable conditions, yields
polyethyne or polyacetylene
2n HC ≡ CH -------------> –( – CH = CH – CH = CH –)n –
Polyethyne
Can You Crack it
Complete the following reaction by identifying X and Y.
NaNH2 C2H5Br
CH3CH2C ≡ CH ----------> X --------------> Y

(a) X = CH3CH2COONa, Y = CH3CH2CH = CH2

(b) X = CH3CH2C ≡ CNa, Y = CH3CH2C ≡ CC2H5
(c) X = CH3CH2CH2CH2Na, Y = CH3CH2CH2CH3
(d) X = CH3CH2CH ≡ CNa, Y = CH3CH2—CH—CH3
|
C2H5
Days Class 11th Class 12th
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