NaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand, NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the molecules numbered I to V in order of decreasing acidity. сон COH он H,0 H,CO, IV CH, 1'> 1 > II II (A) V > II > I > II > IV B) II > 1 > V > III IV C) II > V >I > IV > III

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
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NaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand,
NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the
molecules numbered I to V in order of decreasing acidity.
COH
cOH
он
H,0
H,CO,
IV
CH3
II
I
II
(A)
V > II >I > III >
IV
(В)
II > 1 > V >
III
IV
(C)
II > V >I > IV > II
Transcribed Image Text:NaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand, NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the molecules numbered I to V in order of decreasing acidity. COH cOH он H,0 H,CO, IV CH3 II I II (A) V > II >I > III > IV (В) II > 1 > V > III IV (C) II > V >I > IV > II
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