CH 2_3: UNSATURATED

HYDROCARBON - Alkynes
Prepared by:
Arbanah Muhammad
arbanah@micet.unikl.edu.my

TOPIC COVERED:
1. Alkynes

2. Nomenclature Of Alkynes
3. Properties Of Alkynes
4. Synthesis Of Alkynes
5. Reactions Of Alkynes

Alkynes
Contain carbon carbon triple bonds
Alkynes

RCCR

General formula

CnH2n2

Unsaturated hydrocarbon
Aliphatic hydrocarbons

Example:

Physical properties
1. Similar to alkanes and alkenes
2. Solubility
- Soluble in nonpolar solvent
- Not soluble in water
3. Low density,boiling point and melting point
4. Properties vary based on chain size
Density
Boiling point
Melting point

Increase as the
number of carbon
increase.

Linear

Naming Alkynes
Similar to Alkenes:
1. Longest chain must contain the triple bond
2. Number of carbons so that the triple bond has the lowest
possible value
3. Indicate the position of the triple bond
4. Change ending to - yne

Exercise:

Exercise: Draw the structure from the following IUPAC

name:
5-propyl, 2- octyne
2,5,5-trimethyl, 3- heptyne
1-bromohex-3-yne

Synthesis of alkynes

Dehydrohalogenation
Geminal dihalide
Vicinal dihalide

Synthesis of alkynes
Dehydrohalogenation of dihaloalkane
i. Geminal dihalide
R

R + 2NaNH2

Geminal dihalide

Sodium amide

RC

CR'

alkyne

+
2NH3

Ammonia

+
2NaX
Sodium halide

Reaction :
1st step
R

H
R + NaNH2

RC

X
CR'

+ NH3 + NaX

2nd step
H
RC

X
CR' + NaNH2

RC CR'
+ NH3 + NaX

Synthesis of alkynes
Dehydrohalogenation of dihaloalkane
ii. Vicinal dihalide
R

R + 2NaNH2

Vicinal dihalide

Sodium amide

RC

CR'

alkyne

+
2NH3

Ammonia

+
2NaX
Sodium halide

Exercise:
Provide a reaction to produce octyne from
the reaction of
1) Geminal dihaloalkane
2) Vicinal dihaloalkae
With sodium amide

Reaction of alkynes
1. Hydrogenation
2. Dehydrohalogenation
3. Hydration

Reaction of alkynes

1. Hydrogenation of Alkynes
RC

CR'

2H2

H H

cat

RCCR'

Alkyne

catalyst = Pt, Pd, Ni, or Rh

1 step
st

RC

CR' +

H2

cat

2nd step
H

+ H2

cis alkene H

H H

R
C

R
C

H
R

H Alkane

cat

RCCR'
H

2. Hydrohalogenation of alkynes
H X
RC

CR

Alkyne

+ 2HX
Hydrogen halide

RCCR
H ends
up on the
carbon with the most
H Xto start
hydrogen
dihaloalkane
with

Follow Markonikovs rule

Alkynes are slightly less reactive than alkenes

Reaction of alkynes
Example
1st step

Br H

CH3(CH2)3C

CH + HBr

1-hexyne

Hydrogen
bromide

CH3(CH2)3C

CH

2-bromo-1-hexene

2nd step
Br H
CH3(CH2)3C

CH

Br H
+ HBr

CH3(CH2)3C

CH

Br H
2,2-dibromohexane

Reaction of alkynes
3. Halogenation of alkynes
RC

CR

Alkyne

2X2

X X
RCCR

Hydrogen halide

tetrahaloalkane

Cl Cl

Example
HC

CCH3 + 2Cl2

1-propene

catalyst

HC
Cl

CH3

Cl

tetrachloropropane
Catalyst = AlCl3 / FeCl3

Reaction of alkynes
4. Hydration of alkynes
RC

CR'

+ H2O

H2SO4
HgSO4

RCH2CR'
O

R = alkyl; Ketone
R = H; Aldehyde

Example
CH3CH2C
1-butyne

CH + H2O

H2SO4
HgSO4

O
CH3CH2CCH3
2-butanone

Exercise:
What is the products of the reaction of
hexyne with:
1) Hydrogen
2) Hydrogen flouride
3) Chloride
4) Water