Reactions of Alcohols & Phenols

Interactive Drawing Problem — Interactive problem: select an alcohol/phenol and a reagent, then draw the expected product.
Note: The molecular drawing editor (JME) requires conversion to a modern JavaScript alternative. The problem selection interface below is functional.

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.

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