1. general formula 3 main families
    • Alcohols
    • Phenols
    • Ethers
  2. General formulas are considered organic derivitives of
  3. Molecules are _____ around the oxygen because _____________.
    bent; electrons repel eachother
  4. (R)=
    Hydrogen and alkyl group/ any hydrocarbon group
  5. (Ar)=
    Aryl group (aromatic)
  6. Water General Formula
  7. Alcohol General Formula
  8. Phenol General Formula
  9. Ether General Formulas
    • R-O-R'
    • R-O-Ar
    • Ar-O-Ar'
  10. ____ is functional group in alcohols and phenols.
  11. _____ is functional group in ethers.
  12. _______ don't have functional groups because ________.
    Alkanes; they're saturated and only have single bonds
  13. FG of alkenes
    double bond
  14. FG of alkynes
    triple bond
  15. Primary/Secondary/Tertiary alcohols happen when ___.
    OH is attatched to a Primary/Secondary/Tertiary carbon.
  16. IUPAC Alcohol Naming:
    • - longest chain with OH group (OH becomes top priority, gets lowest #)
    • -in cyclic compounds, OH gets #1 position (assumed so no need to name)
    • -end names in -ol, and when more than one, write out full alkyl or aryl name with a di or a tri ie 1,2,3 butanetriol
  17. IUPAC of methyl alcohol
  18. IUPAC of ethyl alcohol
  19. IUPAC of propyl alcohol
  20. IUPAC of isopropyl alcohol
  21. IUPAC of butyl alcohol
  22. IUPAC of ethylene glycol
  23. IUPAC of propylene glycol
  24. IUPAC of glycerine or glycerol
  25. glycol means
    • >1 OH
    • but it is common not IUPAC
  26. Hydrogen bonds:
    • not real "bonds"
    • very strong intermolecular force that has a great effect on physical properties of alcohols (alcohols have higher BPs because of this)
    • carbon and hydrogen have similar electronegativity so they attract well
  27. Soluable alcohols have ______ carbons.
    1-3; can disolve because of the hydrogen bonds unlike alkanes
  28. As length of hydrocarbon chain increases, _________ decreases.
  29. _________ is insoluable in water.
    1-decanol, because the chain is non-polar while the OH is polar
  30. Properties of alcohol +ether boiling points:
    • much higher than corrosponding alkanes because of hydrogen bonding
    • the more OH groups, the more H bonds, the higher the BP
    • ethers have no H bonds so they have lower BP than alcohols but higher than hydrocarbons
    • similar mass BP comparison:
    • alkane<ethers<alcohols<diols<triols< ect.
    • alkanes have non-polar H bonding, goes up from there
  31. butyl (n-butyl) structure
  32. sec-butyl
    • CH3–CH2–CH(CH3)-----
    • aka 1-methylpropyl
  33. tert-butyl
    • (CH3)3C------
    • aka 1,1-dimethylethyl
  34. isobutyl
    • (CH3)2CH–CH2----
    • aka 1,1-dimethylethyl
  35. n-butyl alcohol, structure and IUPAC name?
    • CH3-CH2-CH2-CH2-OH
    • 1-butanol
  36. sec-butyl alcohol, structure and IUPAC name?
    • CH3CH(OH)CH2CH3
    • 2-butanol
  37. tert-butyl alcohol, structure and IUPAC name?
    • (CH3)3COH
    • 2-methyl-2-propanol
  38. hydration:
    • alkene +H2O----> alcohol
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    • acid catalyst such as H2SO4 or just write H+
    • uses Markavnikov's rule (H goes with his friends)
  39. dehydration
    • 2 types, both use H2SO4 (sulfuric acid) as a catalyst
    • 1) alcohol--->alkene + H2O when you have excess acid (H2SO4)
    • 2) alcohol--->ether + H2O when you have excess alcohol (still have catalyst of H2SO4)
  40. oxidation
    • results depend on if alcohol is primary, secondary, or tertiary
    • oxidizing agents can be KMnO4 or K2Cr2O7 (potassium dichromate)
    • H+ (acid) catalyst
    • put oxidizing agent over catalyst ---->
    • if   =O is on end, it's an aldehyde
    • if   =O is on a sec. carbon, it's a ketone
  41. catalysts for hydration, dehydration, oxidation (and oxidizing agent for this one)?
    • hydration: H+ such as H2SO4
    • dehydration: H2SO4
    • oxidation: H+ cat., oxidizing agents can be KMnO4 and K2Cr2O7
  42. Markovnikov's Rule:
    • OH group goes on C with fewest hydrogens
    • H goes on C with most hydrogens
  43. Properties of Methanol:
    • previously made from wood
    • 1 ton of wood = only 35lbs of methanol
    • nickname is Wood Alcohol
    • now made with 2H2 + CO ------>
  44. Properties of Ethanol:
    • made from sugars and starches (potatoes, corn, wheat, rice, grapes) by fermentation
    • nickname is Grain Alcohol
    • enzymes as catalyst
  45. alcohol proof=
    • 2x percentage of alcohol by volume
    • ie 100 proof is 50% alcohol
  46. All simple alcohols are _______ to some degree.
  47. LD50
    • lethal dose to 50% of population
    • tested on animals
    • varies by species
  48. Methanol is used as a
    commercial solvent for paints
  49. The most toxic alcohol is
    • methanol
    • can cause blindness or death
    • 100mL is fatal to most
    • causes liver enzymes to form formaldehyde
  50. Antidote to methanol is
    ethanol bc liver enzymes prefer the ethonol reaction bc it forms acetaldehyde which isn't nearly as toxic
  51. Ethanol is used as
    • a solvent for perfumes, medicines, mouthwashes, beverages
    • gasoline additive
  52. Ethanol used for industrial purposes is
    • not taxed so it is denatured so no one can drink it
    • denatured= added poisionous things like methanol
  53. Ethanol is fatal when you injest approxamately
    • 1L
    • prolonged exposure causes deteriation of liver, memory loss, addiction
    • most serious drug problem in US
  54. Properties of isopropyl alcohol:
    • nickname: rubbing alcohol
    • evaporates quickly
    • cooling effect
    • antiseptic
    • more toxic than ethanol but induces vomiting so usually not fatal
  55. Polyhydric groups have
    more than one OH group
  56. dihydric alcohols are also known as
    glycols (-diols)
  57. trihydric alcohols are also known as
    glycerols (-triols)
  58. Ethylene glycol is commonly used as an _______ because of its _______.
    • anti-freeze; higher boiling point, non-corrosiveness, lowers freezing point
    • -toxic
  59. Propylene glycol is commonly used as a
    • solvent for drugs
    • moisturizing agent for foods
    • non-toxic
  60. Glyderol/ Glycerine is a sweet, syrupy liquid used for
    • lotions, lubricant, suppositories
    • solvent for medicines
    • non-toxic
  61. Nitroglycerine properties:
    • the product of glycerine + nitric acid
    • reaction produces temps of 3000 deg C and 2000atm
    • detonates on impact, dynamite
    • heart medication when having a heart attack
  62. Ether properties:
    • very inert- don't react very much (all react with O2 though)
    • cumbustable
    • heavy-stick around for a while; dangerous
    • lower BP than alcohols
  63. diethyl ether was the
    first general anesthetic produced in 1846
  64. Other Anesthetics:
    • N2O
    •      dinitrogen monoxide
    •      laughing gas-for conscious sedation
    • CHCl3
    •      chloraform
    •      narrow line between effective dose and lethal dose
    • haloalkane
    •      non-flamable, safer, less nausia
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    • toluene
    • IUPAC methyl benzene
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    • phenol
    • IUPAC hydroxy benzene
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    • m-xylene (can be either o,m or p)
    • IUPAC (1,2 or 1,3 or 1,4 dimethyl benzene)
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    • (TNT)
    • IUPAC trinitrotoluene
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