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Solutions for Carboxylic Acids
Ph H
O
H+
Ph H
O
H
HOCH3
Ph H
O
H
O
CH3H
HOCH3
Ph H
O
H
O
CH3
H+
Ph H
O
H
O
CH3
H
Ph
C
H
O
CH3
HOCH3
Ph H
O
CH3
O
CH3
H
HOCH3
Ph H
O
CH3
O
CH3
HOCH3
H+
Ph OH
O
Ph OH
O
H
OPh
O
CH3
H
Ph OH
O
H
O
CH2H
Ph OH
O
H
O
CH3
Ph OH
O
H
O
CH3
H
H+
Ph O
CH3
O
HOCH3
HOCH3
13 For the sake of space in this problem, resonance forms will not be drawn, but remember that they 
are critical! The generic acid HA is represented here by just H+.
plus resonance forms
– H2O
plus resonance forms
plus resonance forms
– H2O
plus resonance forms
HERE'S THE DIFFERENCE!
CANNOT LOSE H+ TO
MAKE CARBONYL
CAN LOSE H+ TO
MAKE CARBONYL
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