Practicing Success
Case: Read the passage and answer the following questions Alcohol can be prepared in many ways. Alcohols are prepared from alkenes by acid catalysed hydration and by hydroboration–oxidation. Alcohols are even prepared from ketones and aldehydes by reduction. The reduction of carboxylic acid and ester leads to the formation of alcohol. Alcohols are produced by the reaction of Grignard reagents with aldehydes and ketones. Phenol, also known as carbolic acid, was first isolated in the early nineteenth century from coal tar. Nowadays, phenol is commercially produced synthetically. In the laboratory, phenols are prepared from benzene derivatives in many ways. |
Propanone on reaction with alkyl magnesium bromide followed by hydrolysis will produce; |
Primary alcohol Secondary alcohol Tertiary alcohol All of these |
Tertiary alcohol |
The correct answer is option 3. Tertiary alcohol. Propanone (acetone) reacts with alkyl magnesium bromide (Grignard reagent) followed by hydrolysis to produce a tertiary alcohol. Reaction: 1. Reaction with Grignard Reagent: Propanone (acetone) has a carbonyl group. The Grignard reagent (R-MgBr) provides a nucleophilic alkyl group (R⁻) that attacks the electrophilic carbonyl carbon. This forms an alkoxide intermediate. 2. Hydrolysis: The alkoxide intermediate is then hydrolyzed with water (H₂O) to produce the tertiary alcohol. The final product is a tertiary alcohol because the carbon atom attached to the hydroxyl group (OH) is also bonded to three other carbon atoms. Conclusion: Propanone on reaction with alkyl magnesium bromide followed by hydrolysis will produce: Tertiary alcohol. |