Advanced Organic test 2
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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.
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
Why is LDA ~ 100 times
more basic than sodium amide?
LDA has longer carbon chains off of the N group near the Li atom
- 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).
Alkyl groups, which are
slightly e- donating, will destabilize anions. True or false
- 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
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
Acidity of halogens
better acid CH3-H or CH2NH-H
R3-CH2-h or R-CH2-H
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