Organic Test 4

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  1. Nucleophilic Substitution
    Any reaction that is where a nucleophile is substituted for another at the tetravalent carbon (four sided).
  2. Nucleophile
    Negatively charged ion or molecule that donates electrons (Lewis base).
  3. Electrophile
    Positively charged anion or molecule that accepts electrons (Lewis acid).
  4. β-elimination
    • A reaction in which a halide and a hydrogen on the neighboring beta carbon are removed.
    • *E1 and E2 reaction/mechanisms*
  5. EReaction/Mechanism Steps
    (second order reaction)
    • Steps occur simultaneously:
    • 1. (rate determining step/slow) strong base removes beta hydrogen causing electron to collapse and form double bond on carbon attached to Lv group
    • 2. new double bond causes the bond between the leaving group to break 
    • 3. Lv group falls off
    • *strong base needed to break bonds of relatively stable molecule*
  6. Name the strong bases/weak acids.
    • H2O
    • NH3  
    • CH3OH (methoxide)
    • -CΞCH (acetylide)

  7. Protic solvent
    • donates a hydrogen bond
    • water
    • methanol
    • ethanol
    • acetic acid
    • formic acid
  8. Aprotic solvent
    • does NOT donate a hydrogen bond
    • Polar:                         Nonpolar
    • DMSO                         diethyl ether
    • acetonitrile                  toluene
    • aceton                        hexane
  9. Zaitev's Rule
    During beta elimination, the double bond will form on the most stable beta carbon (highest degree carbon)
  10. E1 Reaction/Mechanism Steps
    • 1. (rate determining step/slow)Lv group leaves by itself
    • Can have carbocation rearrangement
Card Set
Organic Test 4
Chapter 9
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