Reactions of Alcohols & Phenols
In this problem we shall consider six hydroxyl group
reactants:
1-propanol
2-butanol
2-methyl-2-propanol
cyclohexanol
phenol
benzyl alcohol
These compounds may be reacted with nine different
reagents:
(CH
3
CO)
2
O
in pyridine
SOCl
2
pyridine, heat
HBr (48%)
heat
CrO
3
aqueous H
2
SO
4
C
5
H
5
NH • ClCrO
3
(PCC) in methylene chloride
H
2
SO
4
heat ( >150 ºC)
C
7
H
7
SO
2
Cl
(tosyl chloride) in pyridine
HNO
3
dilute aqueous
(CH
3
O)
2
SO
2
(dimethyl sulfate) in NaOH soln
Select one hydroxyl compound from the first group,
and one reagent from the second group.
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