Question

Convert bromomethane to acetone

Answer 1

To convert bromomethane (CH₃Br) to acetone (CH₃COCH₃), you can follow these general steps involving nucleophilic substitution and oxidation:

1. Nucleophilic Substitution: First, bromomethane can be converted to methyl alcohol (methanol) by reacting it with a strong base (like sodium hydroxide, NaOH) in a nucleophilic substitution reaction:

   \(\text{CH}_3\text{Br} + \text{NaOH} \rightarrow \text{CH}_3\text{OH} + \text{NaBr}\)

2. Formation of a Carbonyl Compound: Next, methanol can be oxidized to formaldehyde (CH₂O) using an oxidizing agent like PCC (pyridinium chlorochromate):

   \(\text{CH}_3\text{OH} \rightarrow \text{CH}_2\text{O}\)

3. Nucleophilic Addition: Finally, formaldehyde can be subjected to a nucleophilic addition reaction with another equivalent of methanol in the presence of an acid catalyst, followed by dehydration to yield acetone:

   \(\text{CH}_2\text{O} + \text{2 CH}_3\text{OH} \rightarrow \text{CH}_3\text{COCH}_3 + \text{H}_2\text{O}\)