Asked by Micaiah Blackford on Jun 04, 2024

verifed

Verified

What compound is formed when methyloxirane is reacted with ethylmagnesium bromide followed by treatment with aqueous acid?

A) 1-pentanol
B) 2-pentanol
C) 2-methyl-1-butanol
D) 2-methyl-2-butanol
E) 3-methyl-1-butanol

Methyloxirane

A three-membered epoxy ring molecule with a methylene group, used as a chemical intermediate in organic synthesis.

Ethylmagnesium Bromide

A Grignard reagent represented as C2H5MgBr, used in organic synthesis to form carbon-carbon bonds.

Aqueous Acid

An acid solution in which water is the solvent, capable of donating protons (H+ ions) in a reaction.

  • Examine the results of certain chemical reactions based on the reactants and conditions provided.
  • Forecast the outcome of interactions between epoxides and diverse reactants.
  • Utilize organic chemistry principles to forecast the results of reactions.
verifed

Verified Answer

ZK
Zybrea KnightJun 07, 2024
Final Answer :
B
Explanation :
The reaction between methyloxirane (a three-membered epoxy ring with a methyl group attached) and ethylmagnesium bromide (a Grignard reagent) involves the nucleophilic attack of the ethyl group on the less hindered carbon atom of the oxirane ring, leading to ring opening. This results in a primary alcohol after the addition of the ethyl group to the carbon atom next to the methyl group. Upon subsequent treatment with aqueous acid, protonation occurs, yielding the alcohol. The product is 2-pentanol, as the ethyl group attaches to the second carbon in the chain, counting from the end nearest the original methyl group, making a five-carbon chain with the hydroxyl group on the second carbon.