Organic Chemistry

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Author:
JessieP
ID:
10964
Filename:
Organic Chemistry
Updated:
2010-03-22 14:42:02
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Ch 11
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Description:
Alcohols and Ethers
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  1. 
    • Ether
    • Oxygen partially negative
    • Carbons partially positive
    • More Soluble in water than hydrocarbons
    • Lower bp than alcohols
    • Oxirane
    • high strain on carbons
    • undergoes many ring-opening reactions with nucleophiles
  2. Oxetane
  3. Oxolane
  4. oxane
    • Crown Ether
    • 18-Crown-6
    • Alkoxide
    • Epoxide
    • Simple epoxides named based off oxirane
    • More complex = epoxy
    • Peroxycaroxylic acid
    • used in epoxide synthesis
  5. Glycol
    • Epichlorohydrin
    • each 3 carbons have a reactive functional group
    • Thioether
    • S rather than O
    • Alcohol
    • sp3 hybridized
    • 10 20 30
  6. Lewis Acid
    Can accept electrons
  7. Lewis Base
    Donates a pair of electrons
  8. Electrophile
    • "electron-lover"
    • accepts electrons (lewis acid)
    • usually positivelt charged
  9. Nucleophile
    • "nucleus-lover"
    • donates a pair of electrons (Lewis base)
    • Willaimson Ether Synthesis
    • best when leaving group is primary or methyl
    • Sn2
    • Typically O+Na- with Br+ or I+ leaving group
    • Alkoxide is the nucleophile
  10. 2(CH3)-C=CH2 + CH3OH --> 3(CH3)-C-O-CH36y
    • Acid-Catalyzed Addiction of Alcohols
    • Alkenes that form stable carbocations
    • Methanol or primary alcohols
    • 1. Acid protonates carbon
    • 2. Electrophilic carbocation reacts with nucleophilic alcohol to make oxonium
    • 3. Proton transfer to solvent to stabalize
  11. CH3(3CH2)-O-(3CH2)CH3 + 2 HBR --heat--> 2 CH3(3CH2)Br + H2O
    • Acid-Catalyzed Cleavage of Concentrated HX
    • Requires strong acid and good nucleophile (HI or HBR)
    • If both carbons are primary... Sn2
    • Otherwise... Sn1
    • Tertiary, allylic or Benzylic ethers are particularly susceptible
    • Epoxidation of an Elkene by Peracid Oxidation
    • Nonpolar solvents
    • stereospecific!
    • Epoxide and carboxylic acid product
  12. Insert picture from phone
    • Internal Substitution of Halohydrin
    • 1. Treat alkene with Br2 or Cl2 in water
    • 2. treat halohydrin with a base (NaOH) to displace Cl or Br

    • Stereoselective
    • Internal Sn2
    • Inversion of configuration
  13. 2 ways to create epoxides
    Perocycarboxylic Acids and Substitutions in Halohydrins
  14. General Characteristics of Epoxide Reactions
    • Epoxide + H-Nu: ----> OH(up)-C-C-Nu(down)
    • Stereoselective

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