Advanced Organic test 2

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Anonymous
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298304
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Advanced Organic test 2
Updated:
2015-03-12 22:54:32
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chemistry
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  1. Why is phenol
    (pka = 10) more than 1 million times more acidic than a secondary
    alcohol (pka = 17)?
    • The conjugate base of
    • phenol is resonance stabilized due to the aromatic ring.
  2. Find the
    structure of tosic acid (para-toluenesulfonic acid). Why is
    tosic acid so strong (pka ~ -6.5)? How does this relate to the
    fact that the tosyl group is a very good leaving group?
    S based rersonance
  3. Why is LDA ~ 100 times
    more basic than sodium amide?
    LDA has longer carbon chains off of the N group near the Li atom
  4. We
    • have seen that alkyl groups donate electrons to a greater extent
    • than H. This would further destabilize the negatively charged
    • nitrogen, making it more reactive (more basic).
  5. Alkyl groups, which are
    slightly e- donating, will destabilize anions.  True or  false
    true
  6. Friedel-Crafts acylation
    • The AlCl3 acts as a catalyst that helps form the acylium
    • electrophile by stabilizing chloride ion (Cl-). Like
    • nitration, this is an example of electrophilic aromatic
    • substitution.
  7. xplain this result in
    terms of thermodynamics/kinetics using the reaction between sodium
    methoxide and 2-ethyloxirane as an example. ( A:E) why is the do reactents attacking a ring with an oxygen attack the less hinderded side
    negative charge likes to be on the oxygen near two carbons to draw electrons from isntead of jsut one
  8. Acidity of halogens
    I>Br>Cl>F
  9. better acid CH3-H or CH2NH-H
    CH2NH-H
  10. R3-CH2-h or R-CH2-H
    R-CH2-H

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