Which of the following compounds gives a primary alcohol upon reaction...
Primary alcohols are formed when a Grignard reagent reacts with an epoxide. In this case, the compound that gives a primary alcohol upon reaction with phenylmagnesium bromide is ethylene oxide.
- Epoxides are cyclic ethers with a three-membered ring containing an oxygen atom.
- Phenylmagnesium bromide (C6H5MgBr) is a Grignard reagent that contains a carbon-magnesium bond.
- Grignard reagents are highly reactive and can undergo nucleophilic addition reactions with a variety of electrophilic compounds.
- When phenylmagnesium bromide reacts with ethylene oxide, the oxygen atom of the epoxide is nucleophilically attacked by the carbon atom of the Grignard reagent.
- This results in the opening of the epoxide ring and the formation of a new carbon-oxygen bond.
- The product of this reaction is a primary alcohol, which has a hydroxyl group (-OH) directly attached to a carbon atom that is bonded to only one other carbon atom.
- In the case of ethylene oxide, the reaction with phenylmagnesium bromide would result in the formation of 1-phenylethanol.
- The hydroxyl group (-OH) is directly attached to the carbon atom that was previously part of the epoxide ring, which makes it a primary alcohol.
- The other compounds listed, 2-methyloxirane, ethyl formate, and carbon dioxide, do not have a carbon atom that can react with the Grignard reagent to form a primary alcohol.
- Therefore, only ethylene oxide gives a primary alcohol upon reaction with phenylmagnesium bromide.
Which of the following compounds gives a primary alcohol upon reaction...
Ethylene oxide reacts with Grignard reagents to give, after protonation, primary alcohols with two additional carbon atoms.