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1. "Rank the following molecules in terms of their increasing acid strength; 1-weakest acid, 4-
strongest acid. Give brief explanations for your choices." OH OH OH NO2 CH3
Solution
Electron withdrawing groups (NO2) increases the acidity while electron donating groups (CH3)
decreases the acidity.
So, O-Cresol (o-methyl phenol, and weak acid) < cyclohexanol < cyclohexenol < o-nitro phenol
(strong acid).
And compounds with OH group on sp2 carbon are more acidic than compounds with sp3 due to
resonance factors which involves delocalisation on alkoxide.

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