Home > Community > What are the products of the reaction of methoxypropane with HBr?
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Matt Walsh

What are the products of the reaction of methoxypropane with HBr?

Bruce R. Miller  Follow

The first step is protonation of the oxygen of the ether. This cationic species is then subject to nucleophilic attack by Br-. There are two potential sites of attack i.e. the carbons bonded to the protonated oxygen. Bromine is quite a bulky nucleophile, and of the two sites, the methyl group carbon is less hindered so this is attacked in preference, leading to bromomethane and propan-1-ol as your products.

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Jim Short  Follow
dropbox.com/s/dukb3mewv2vy8g5/…More
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John Flavin  Follow
With excess HBr propan-1-ol will also react to form 1-bromopropane.More
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Jack E. Leonard  Follow
In a real experiment yes, probably get measurable quantities of 2-bromopropane and propene tooMore
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John Privett  Follow
Goes by a different mechanism. The protonated ether in that case fragments to give tBu cation, this is very stable and drives the reactionMore
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John Allen  Follow
so steric hindrance is the reason. Then, what would you say about this More
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