1 / 54

Alcohols and Phenol

Alcohols and Phenol. Chapter 4. Bonding. Covalent bonds can be either polar or non polar Polar – covalent bonds with equal sharing of e-’s Non-Polar – covalent bonds with unequal sharing of e-’s. Non-Polar Bonds. Always form nonpolar molecules Equal distribution of electrons

frieda
Download Presentation

Alcohols and Phenol

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Alcohols and Phenol Chapter 4

  2. Bonding • Covalent bonds can be either polar or non polar • Polar – covalent bonds with equal sharing of e-’s • Non-Polar – covalent bonds with unequal sharing of e-’s

  3. Non-Polar Bonds • Always form nonpolar molecules • Equal distribution of electrons • No charged areas

  4. Polar Bonds • In symmetrical molecules  nonpolar molecules • Bonds are equidistant from each other if symmetric • In unsymmetrical molecules polar molecules • Charged areas due to uneven e- distribution

  5. Polar Bonds σ+ σ- H – Cl

  6. Attractive Forces in Molecules • Nonpolar molecules are held together by LDF (attractions between temporary dipoles and induced dipoles) • Induced dipoles – temporary dipoles formed by the attraction of one atoms nucleus for another atom’s e-’s

  7. Polar Molecules are held together by either… • Dipole-Dipole attractions • Attraction between oppositely charged poles on 2 polar molecules • Hydrogen Bonds (very strong dipole-dipole) • The attraction between the + charges H on one dipole and the – charged highly e-neg element in the polar molecule.

  8. Strength • Order of strength… • H-Bond>dipole-dipole>LDF

  9. Functional Groups • Both alcohols and phenol contain OH • OH – Hydroxyl group • Alcohol  General Formula = R-OH • Phenol  General Formula = Ar-OH

  10. The Difference • The difference between alcohols and phenol is the O added to make the OH group • Results in 3 differences…

  11. The Difference • 1. Alkanes = nonpolar molecules with LDF • Alcohols = have polar areas and H Bonding • C – C – C – O H σ- σ+ Nonpolar Region

  12. The Difference • 2. Alkanes cannot dissolve in H2O while shorter (2-5 C’s) alcohols can • 3. Alcohols have higher boiling points that their corresponding alkanes

  13. The Difference • C = -162 °C C-OH = 64.5 °C • C-C = -88.5 °C C-C-OH = 78.3 °C • C-C-C = 0 °C C-C-C-OH = 118 °C

  14. The Difference • 1° alcohol – hydroxyl group on 1° C C-C-C-OH • 2° alcohol – hydroxyl group on 2° C C-C-C OH • 3° alcohol – hydroxyl group on 3° C C C-C-C OH

  15. Naming Alcohols • Drop –e from the alkane & add –ol • # from end closest to –OH & add the # in front of the “main”chain • The –OH has priority over other functional groups covered

  16. Name the following…& write the condensed formula  • C-C-C-OH C-C-C-C-C-C-OH OH • C-C-C-C-C-C-C OH OHOHOHOH • C-C-C-C C-C-C-C-C

  17. More Practice  Name & Condensed Cl OH C OH • C-C-C-C C-C-C-C-C-C Br BrBr OH • C-C-C-C-C-C-C-C-C OH OH • C-C-C-C-C C-C-C-C-C

  18. Still More Practice! Name & Condensed OH OH • C-C-C-C-C-C-C OH OHOHCl OH Cl • C-C-C-C-C-C C-C-C-C-C-C-C C-C

  19. Preparation of Alcohols • 1°Alcohols a.) Alkyl halide + water  alcohol + hydrogen halide RX + H2O  R-OH + HX Form 1-Propanol (str & cond) Cl OH C-C-C + H2O  C-C-C + HCl CH3CH2CH2Cl + H2O  CH3CH2CH2OH + HCl

  20. Reaction Practice • React ethylfluoride with water (str,cond, name product)

  21. Preparation of Alcohols (still 1°) b.) Alkyl + metal  alcohol + metal halide hydroxide halide RX + M+OH-  ROH + MX (M Can be Li+,Na+,or K+)

  22. Practice • Form Heptanol (str and Cond) (you can choose any of the 3 metals – Na is most common)C-C-C-C-C-C-C-Cl + NaOH C-C-C-C-C-C-C-OH + NaCl CH3(CH2)5CH2Cl + NaOH  CH3(CH2)5CH2OH + NaCl

  23. Practice • React methyl bromide with potassium hydroxide

  24. Synthesize • Synthesize – to form an organic compound from the pure hydrocarbon (usually needs more than one step) • Synthesis of a 1° Alcohol requires 2 steps • RH + Cl2 RCl + HCl • RCl + H2O (or NaOH)  ROH + HClNa could be Li or K (or NaCl)

  25. Examples • Synthesize methanol (str) • C + Cl2 CCl + HCl • CCl + NaOH (or H2O)  COH + NaCl (or HCl)

  26. Examples • Synthesize 1-Pentanol (condensed) CH3(CH2)3CH3 + Cl2 CH3(CH2)3CH2Cl + HCl CH3(CH2)3CH2Cl + KOH (or H2O)  CH3(CH2)3CH2OH + KCl (or HCl)

  27. Preparation of 2° or 3° Alcohol • Alkene + water 2° or 3° Alcohol Hydrate 3-ethyl-2-pentene (str,cond,nameprdct)

  28. Preparation of 2° or 3° Alcohol 2. RX + H2O  ROH + HX • React 3-iodoheptane with water (str, cond, name product)

  29. Preparation of 2° or 3° Alcohol 3. RX + M+OH- ROH + MX React 2-fluoropropane with Lithium Hydroxide (str, cond, name product)

  30. Practice • Form 2-hexanol 3 ways (str) • Form 3-octanol 3 ways (cond) • Synthesize 2 - Butanol

  31. Reactions of Alcohols • Halogenation (same as alkanes) R-OH + X2 R-XOH + HX Form 3-bromo-1-heptanol (3-bromoheptanol) (str and cond) Br C-C-C-C-C-C-C-OH +Br2  C-C-C-C-C-C-C-OH

  32. Practice • Form 1,2,2,3-tetrafluorohexanol (*1-hexanol) (str&cond) Form 3-iodo-3-hexanol (str&cond)

  33. Reactions of Alcohols 2. Alcohol + hydrogen halide  alkyl halide + water ROH + HX RX + H2O React methanol with hydrogeniodide(str, cond, name product) CH3-OH + HI  CH3-I + H2O

  34. Practice • React 2-pentanol with Hydrogen Fluoride (str, cond, name product)

  35. Reactions of Alcohols 3. Dehydration of alcohols to form alkenes Alcohol –H2SO4alkene + H2O Dehydrate 2-butanol (str&cond) OH C-C-C-C –H2SO4C=C-C-C + H2O

  36. Reaction Mechanism for Dehydration of Alcohols • H • C-C-OH + H+ C-C-O-H+ • H • C-C-O-H+  C-C+ + H2O • C-C+  C=C + H+ • H Indicated Protonated Alcohol

  37. Protonated alcohol – an alcohol where a H+bonds coordinately to the hydroxyl group giving the alcohol a positive charge

  38. Reactions of Alcohols 4. Alcohol + metal  alcohol salt + H ROH + M  RO-M+ + ½ H2 *M = Na+,K+, Ba+2, Ca+2, Mg+2, Al+3

  39. Reactions of Alcohols • React ethanol with Barium • C-C-OH + Ba  (C-C-O-1)2Ba+2+ H2 • Condensed:

  40. To Name Alcohol Salts • Name Metal • Prefix for # of C’s and follow with – oxide (C-C-O-1)2 Ba+2 = barium ethoxide

  41. Practice • React pentanol with lithium (str, cond, name product) 2-C-C-C-C-C-OH + 2Li  2C-C-C-C-C-O-1Li+ + H2 (Coefficient for H2 groups at the end) Condensed: Name:

  42. Practice • React methanol with Al (str, cond, name product)

  43. Practice • Synthesize barium octoxide (cond.)

  44. Reactions of Alcohols 5. Alcohol + metal hydroxide  alcohol salt + water ROH + M+1OH-1  RO-M+ + H2O React ethanol with lithium hydroxide (str,cond, name product) C-C-OH + LiOH  C-C-O-1Li+ + H2O Lithium ethoxide

  45. Practice • React propanol with Mangesium hydroxide [Mg(OH)2] (balance it) • React pentanol with aluminum hydroxide (balance it) • Form barium nonoxide 2 ways (condensed)

  46. Phenol • General form: ArOH C6H5OH • Nomenclature: Orthobromophenol or 2-bromophenol (-OH = #1 position) 2,3 – dibromophenol

  47. Preparation of Phenol • ArCl + H2O or NaOH ArOH + HCl or NaCl • Synthesis of phenol: ArH + Cl2 –FeCl3 ArCl + HCl ArCl + H2O or NaCl  ArOH + HCl or NaCl Do synthesis structurally

  48. Reactions of Phenol • Halogenation: ArOH + X2 –FeX3 ArXOH + HX Form 2,4-diiodophenol

  49. Reactions of Phenol 2. Nitration: ArOH + HNO3–H2SO4ArNO2OH + H2O Form 2,3,5-trinitrophenol

  50. Reactions of Phenol 3. Friedel-Crafts Alkylation: ArOH + RCl –AlCl3 ArROH + HCl Form metapropylphenol

More Related