2. Reactions, alkenes:
1. Addition of hydrogen (reduction).
2. Addition of halogens.
3. Addition of hydrogen halides.
4. Addition of water (hydration).
5. Polymerization
3. Reactions of Alkenes
C C
OH
H
Alcohol
H
H
OH
HO
1,2-Diol
O
C
O
X
H
X
X
OH
X
Alkane
Carbonyl Compound
Cyclopropane
Epoxide
1,2-Dihalide
Halide
Halohydrin
alkene
4. 1. Addition of hydrogen (reduction).
| | | |
β C = C β + H2 + Ni, Pt, or Pd ο β C β C β
| |
H H
a) Requires catalyst.
b) #1 synthesis of alkanes
CH3CH=CHCH3 + H2, Ni ο CH3CH2CH2CH3
2-butene n-butane
5. 2) Addition of halogens.
| | | |
β C = C β + X2 ο β C β C β
| |
X X
a) X2 = Br2 or Cl2
b) test for unsaturation with Br2
CH3CH2CH=CH2 + Br2 ο CH3CH2CHCH2
Br Br
1-butene 1,2-dibromobutane
6. 3. Addition of hydrogen halides.
| | | |
β C = C β + HX ο β C β C β
| |
H X
a) HX = HI, HBr, HCl
CH3CH=CH2 + HI ο CH3CHCH3
I
CH3 CH3
CH3C=CH2 + HBr ο CH3CCH3
Br
10. Plastics: man-made polymers that at some time in their
manufacture are soft and pliable.
Thermoplastics: plastics that soften when heated.
Free radical polymerization.
| | | | | |
Rβ’ + β C = C β ο R β C β C β’ + β C = C β ο
| |
12. Introduction
β’ Alkynes contain a triple bond.
β’ General formula is CnH2n-2
β’ Two elements of unsaturation for each triple
bond.
β’ Some reactions are like alkenes: addition
and oxidation.
β’ Some reactions are specific to alkynes.
=>
13. I. Comparing Hydrocarbons
(Unsaturated Compounds)
Alkanes contain single bonds only -ANE ending
CnH2n+2 (saturated)
Alkenes contain a double bond -ENE ending
CnH2n (unsaturated)
Alkynes contain a triple bond between -YNE ending
CnH2n-2 (unsaturated)
14. Nomenclature: IUPAC
β’ Find the longest chain containing the triple
bond.
β’ Change -ane ending to -yne.
β’ Number the chain, starting at the end closest
to the triple bond.
β’ Give branches or other substituents a
number to locate their position.
=>
15. CH C CH2 CH3
1-butyne
CH3CοΊCCH3 2-butyne
CH3CH2CοΊCCH3 2-Pentyne
17. Name these:
CH3 CH
CH3
CH2 C C CH
CH3
CH3
CH3 C C CH2 CH2 Br
CH3 C CH
propyne
5-bromo-2-pentyne
2,6-dimethyl-3-heptyne =>
18. Common Names
Named as substituted acetylene.
CH3 C CH
methylacetylene
CH3CH2CοΊCCH3 2-pentyne
ethylmethylacetylene
C3H4 CH3CοΊCH methylacetylene
propyne
19. Physical Properties of Alkynes
β’ Nonpolar, insoluble in water.
β’ Soluble in most organic solvents.
β’ Boiling points similar to alkane of same size.
β’ Less dense than water.
β’ Up to 4 carbons, gas at room temperature.
=>
20. Preparation of Alkynes by Double Elimination
2.3
Alkynes are prepared from dihaloalkanes by elimination.