Documente Academic
Documente Profesional
Documente Cultură
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:
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
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
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