O-Chem: Alkene Reaction with HBr and Methanol

In summary, when cis-2-butene reacts with HBr and CH3OH, the two final products can be either bromine on either side of the structure or an alkane. It is unclear how the methanol plays a role in the reaction.
  • #1
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Homework Statement



What are the two final products when cis-2-butene reacts with HBr and CH3OH?

Homework Equations



Reactions of Alkenes.

The Attempt at a Solution



I'm not sure if the HBr will attack the double bond first or if the OH on methane will take the H off HBr and create a radical. This sample final I'm working on does not have a key, so there is no way I can check the correct answer and reverse engineer it.

Thank you :)
 
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  • #2
Remember there are two products-- what product would each of the options you outlined yield?
 
  • #3
Since there are two secondary carbons, I think I could end up with Bromine on either side of the structure and that the cis-2-butene would be an alkane. I don't know how the methanol plays a part in this though. It's not a peroxide.
 

1. What is the purpose of the reaction between an alkene, HBr, and methanol?

The purpose of this reaction is to add a hydrobromic acid (HBr) and a methanol molecule to an unsaturated carbon-carbon double bond (alkene) to form a new carbon-carbon single bond. This results in the formation of a halogenated alcohol, which can have various industrial and pharmaceutical applications.

2. What is the mechanism of the alkene reaction with HBr and methanol?

The mechanism of this reaction involves the protonation of the alkene by HBr to form a carbocation intermediate. The methanol then attacks the carbocation, resulting in the formation of a new carbon-carbon bond and the release of a proton. This is known as an electrophilic addition reaction.

3. What factors can affect the rate of the alkene reaction with HBr and methanol?

The rate of this reaction can be affected by the concentration of the reactants, temperature, and the presence of any catalysts. The stability of the carbocation intermediate can also play a role in the rate of the reaction.

4. Can this reaction lead to the formation of multiple products?

Yes, this reaction can lead to the formation of multiple products. The regioselectivity of the reaction, or the preference for the formation of one product over another, depends on the stability of the carbocation intermediate and the steric hindrance of the reactants.

5. How is this reaction different from the reaction between an alkene and hydrobromic acid alone?

The addition of methanol to the reaction mixture allows for the formation of a halogenated alcohol, whereas the reaction with hydrobromic acid alone would result in the formation of an alkyl bromide. Additionally, the presence of methanol can affect the regioselectivity of the reaction, leading to the formation of different products.

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