When 1-bromopropane is exposed to magnesium, followed by ethylene oxide, and then aqueous acid, what is the resulting product?Select answer from the options below2-methyl-2-hexanol2-methyl-2-pentanol2-pentanol1-pentanol
Question
When 1-bromopropane is exposed to magnesium, followed by ethylene oxide, and then aqueous acid, what is the resulting product?Select answer from the options below2-methyl-2-hexanol2-methyl-2-pentanol2-pentanol1-pentanol
Solution
The resulting product is 2-methyl-2-pentanol.
Here's the step-by-step process:
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When 1-bromopropane is exposed to magnesium, a Grignard reagent is formed. The bromine atom in 1-bromopropane is replaced by a magnesium atom, resulting in propylmagnesium bromide.
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This Grignard reagent then reacts with ethylene oxide. The carbon atom in the Grignard reagent attacks the less substituted carbon atom in the ethylene oxide, opening the epoxide ring and forming a new carbon-carbon bond. This results in a primary alcohol with four carbon atoms.
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Finally, the addition of aqueous acid protonates the alkoxide intermediate, forming the final product, 2-methyl-2-pentanol. This step also removes the magnesium atom, replacing it with a hydrogen atom.
Similar Questions
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What compound provides (S)-2-bromopentane upon exposure to TsCl then NaBr?Select answer from the options below(S)-2-pentanol2-pentene(R)-2-pentanol1-pentene
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