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Chapter 2.1 Reaction of alkenes.ppt

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Alkenes, Reactions
Reactions, alkenes:
1. Addition of hydrogen (reduction).
2. Addition of halogens.
3. Addition of hydrogen halides.
4. Addition of water (hydration).
5. Polymerization
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
1. Addition of hydrogen (reduction).
| | | |
— C = C — + H2 + Ni, Pt, or Pd  — C — C —
| |
H H
a) Requires catalyst.
b) #1 synthesis of alkanes
CH3CH=CHCH3 + H2, Ni  CH3CH2CH2CH3
2-butene n-butane
2) Addition of halogens.
| | | |
— C = C — + X2  — C — C —
| |
X X
a) X2 = Br2 or Cl2
b) test for unsaturation with Br2
CH3CH2CH=CH2 + Br2  CH3CH2CHCH2
Br Br
1-butene 1,2-dibromobutane
3. Addition of hydrogen halides.
| | | |
— C = C — + HX  — C — C —
| |
H X
a) HX = HI, HBr, HCl
CH3CH=CH2 + HI  CH3CHCH3
I
CH3 CH3
CH3C=CH2 + HBr  CH3CCH3
Br

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Chapter 2.1 Reaction of alkenes.ppt

  • 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). | | | | — C = C — + H2 + Ni, Pt, or Pd  — C — C — | | H H a) Requires catalyst. b) #1 synthesis of alkanes CH3CH=CHCH3 + H2, Ni  CH3CH2CH2CH3 2-butene n-butane
  • 5. 2) Addition of halogens. | | | | — C = C — + X2  — C — C — | | X X a) X2 = Br2 or Cl2 b) test for unsaturation with Br2 CH3CH2CH=CH2 + Br2  CH3CH2CHCH2 Br Br 1-butene 1,2-dibromobutane
  • 6. 3. Addition of hydrogen halides. | | | | — C = C — + HX  — C — C — | | H X a) HX = HI, HBr, HCl CH3CH=CH2 + HI  CH3CHCH3 I CH3 CH3 CH3C=CH2 + HBr  CH3CCH3 Br
  • 7. CH3CH2CH=CH2 + HCl  CH3CH2CHCH3 Cl CH3 CH3 CH3CH=CCH3 + HBr  CH3CH2CCH3 Br CH3CH=CHCH3 + HI  CH3CH2CHCH3 I
  • 8. 4. Addition of water. | | | | — C = C — + H2O, H+  — C — C — | | H OH a) requires acid CH3CH2CH=CH2 + H2O, H+  CH3CH2CHCH3 OH
  • 9. 12. Polymerization. CH2=CH2 + heat, pressure  -(CH2CH2)-n n = 10,000+ polyethylene CH3CH=CH2 polymerization  -(CH2CH)-n CH3 polypropylene CH2=CHCl poly…  -(CH2CH)-n Cl polyvinyl chloride (PVC)
  • 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. | | | | | | R• + — C = C —  R — C — C • + — C = C —  | |
  • 12. Introduction • Alkynes contain a triple bond. • General formula is CnH2n-2 • Two elements of unsaturation for each triple bond. • Some reactions are like alkenes: addition and oxidation. • 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 • Find the longest chain containing the triple bond. • Change -ane ending to -yne. • Number the chain, starting at the end closest to the triple bond. • Give branches or other substituents a number to locate their position. =>
  • 15. CH C CH2 CH3 1-butyne CH3CCCH3 2-butyne CH3CH2CCCH3 2-Pentyne
  • 16. c) 5-ethyl-4-methyl-2-heptyne CH CH CH2 CH2 CH3 C C CH3 CH3 CH3
  • 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 CH3CH2CCCH3 2-pentyne ethylmethylacetylene C3H4 CH3CCH methylacetylene propyne
  • 19. Physical Properties of Alkynes • Nonpolar, insoluble in water. • Soluble in most organic solvents. • Boiling points similar to alkane of same size. • Less dense than water. • Up to 4 carbons, gas at room temperature. =>
  • 20. Preparation of Alkynes by Double Elimination 2.3 Alkynes are prepared from dihaloalkanes by elimination.