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:
(CH3CO)2O
in pyridine
SOCl2
pyridine, heat
HBr (48%) 
  heat
CrO3
aqueous H2SO4
C5H5NH • ClCrO3
(PCC) in methylene chloride
H2SO4
heat ( >150 ºC)
C7H7SO2Cl
(tosyl chloride) in pyridine
HNO3
dilute aqueous
(CH3O)2SO2
(dimethyl sulfate) in NaOH soln

Select one hydroxyl compound from the first group,
and one reagent from the second group.
To practice using the drawing program Click Here  
To review the chemistry of alcohols Click Here.