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March 29, 2017

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Experiment= synthesis of n-butyl bromide, using n-butyl alcohol, NaBr, H2SO4. A) An ether and an alkene are formed as by-products in this reaction. Draw the structures of these by-products and give mechanisms for their formation.
I believe the two products are dibutyl ether and 1-butene? I know each of their line structures, but I don't know about the mechanisms? Any Help?

  • Org. Chem. - ,

    I believe the 1-butene forms by an SN1 mechanism and the dibutyl ether forms by E1 mechanism, but I am still not sure which are the nucleophiles, electrophiles, leaving group, etc.?

  • Org. Chem. - ,

    The alkene would be formed via an E1 mechanism because it is formed by an elimination reaction in a dehydration reaction between n-butyl alcohol, a primary alcohol, and sulfuric acid, an obviously strong acid. The ether would be formed via Williamson ether synthesis, which is an SN2 mechanism. I think that the person who answered this question originally should have read the question carefully before answering. If you don't know what you are talking about then please don't answer and lead someone down the wrong path. People who come here are looking to understand how things work, so if you don't know yourself then don't give a bs answer.

  • Org. Chem. - ,

    Actually, primary alcohols undergo a E2 mechanism to form the alkene.

  • Org. Chem. - ,

    burn

  • Org. Chem. - ,

    The person who first answered the question was the same person who posted it. Way to be a hypocrite and complain about people not reading carefully.

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