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11.15 Preparation of Alkenylbenzenes

11.15 Preparation of Alkenylbenzenes. dehydrogenation dehydration dehydrohalogenation. CH 2 CH 3. CH. CH 2. Dehydrogenation. industrial preparation of styrene 11,800,000,000 lbs. produced in U.S. in 1999. 630°C. ZnO. + H 2. Cl. Cl. CH. CHCH 3. CH 2. OH.

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11.15 Preparation of Alkenylbenzenes

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  1. 11.15Preparation of Alkenylbenzenes • dehydrogenation • dehydration • dehydrohalogenation

  2. CH2CH3 CH CH2 Dehydrogenation • industrial preparation of styrene • 11,800,000,000 lbs. produced in U.S. in 1999. 630°C ZnO + H2

  3. Cl Cl CH CHCH3 CH2 OH Acid-Catalyzed Dehydration of Benzylic Alcohols KHSO4 heat + H2O (80-82%)

  4. Cl Cl CH CHCH3 CH2 OH Cl CHCH3 + Acid-Catalyzed Dehydration of Benzylic Alcohols KHSO4 heat (80-82%)

  5. CH2CHCH3 H3C Br CH H3C CHCH3 Dehydrohalogenation NaOCH2CH3 ethanol, 50°C (99%)

  6. 11.16Addition Reactions of Alkenylbenzenes • hydrogenation • halogenation • addition of hydrogen halides

  7. CH3 CH3 C CHCH2CH3 CHCH3 H2 Pt Br Br Hydrogenation (92%)

  8. CH CH2 Halogenation Br2 CH CH2 Br Br (82%)

  9. Cl HCl Addition of Hydrogen Halides (75-84%)

  10. Cl HCl Addition of Hydrogen Halides + via benzylic carbocation

  11. CH CH2CH2Br CH2 Free-Radical Addition of HBr HBr peroxides

  12. CH CH2CH2Br CH2 Free-Radical Addition of HBr HBr peroxides CH CH2Br • via benzylic radical

  13. 11.17Polymerization of Styrene

  14. H2C CHC6H5 CH2 CH CH2 CH CH2 CH C6H5 C6H5 C6H5 Polymerization of Styrene polystyrene

  15. • • • H2C CHC6H5 Mechanism •• RO

  16. • • Mechanism •• RO H2C CHC6H5 •

  17. • • H2C CHC6H5 Mechanism •• RO H2C CHC6H5 •

  18. • • • H2C CHC6H5 Mechanism •• RO H2C CHC6H5

  19. • • Mechanism •• RO H2C CHC6H5 H2C CHC6H5 •

  20. • • H2C CHC6H5 Mechanism •• RO H2C CHC6H5 H2C CHC6H5 •

  21. • • • H2C CHC6H5 Mechanism •• RO H2C CHC6H5 H2C CHC6H5

  22. •• • RO • H2C CHC6H5 H2C CHC6H5 H2C CHC6H5 Mechanism •

  23. •• • RO • H2C CHC6H5 H2C CHC6H5 H2C CHC6H5 H2C CHC6H5 Mechanism •

  24. •• • RO • H2C CHC6H5 H2C CHC6H5 H2C CHC6H5 H2C CHC6H5 Mechanism •

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