Question 27.6: Predicting the Products of a Reaction Involving an Alcohol P...
Predicting the Products of a Reaction Involving an Alcohol
Predict the products of the following reactions. If appropriate, suggest a mechanism by which the reaction occurs by using arrows to show the movement of electrons.
(a) \text{1-propanol} + \text{sodium hydroxide} \xrightarrow{H_2O}
(b) \text{(R)-2-bromo-3-methylbutane} + \text{ethanol} \xrightarrow{\text{ethanol}}
Analyze
First, we write condensed structural formulas for the reactants, and then we consider the role of the alcohol in each case. Alcohols can be oxidized or deprotonated. They can act as either a nucleophile or an electrophile in a substitution reaction or they can be dehydrated. To make a decision, we must consider the α carbon atoms in the reactants and classify them as primary, secondary, or tertiary. We must also consider the other reactants, the solvent, and the reaction conditions.
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