Where are carbo-cations formed in this nucleophilic substitution reaction?

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Discussion Overview

The discussion revolves around the formation of carbo-cations in a nucleophilic substitution reaction involving HBr and methoxide ions. Participants explore the reaction mechanism, specifically focusing on the initial step with HBr and the subsequent step with methoxide ions.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation

Main Points Raised

  • One participant expresses confusion about the formation of carbo-cations in the reaction.
  • Another participant suggests that the hydrogen from HBr would attack the double bonds, leading to the formation of the most stable carbo-cation.
  • A participant emphasizes the need to determine whether the ends of each double bond are primary, secondary, or tertiary carbons to assess the stability of the resulting carbo-cations.
  • There is a mention of a second step involving nucleophilic substitution with methoxide ions, but details about this step remain unclear for some participants.

Areas of Agreement / Disagreement

Participants generally agree on the initial step involving HBr and the formation of carbo-cations, but there is uncertainty regarding the specifics of the second step with methoxide ions. The discussion remains unresolved on the details of this step.

Contextual Notes

Some assumptions about the stability of carbo-cations and the nature of the nucleophilic substitution with methoxide ions are not fully explored, leaving room for further clarification.

Oblivion77
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Homework Statement


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The Attempt at a Solution



I'm confused on what is happening in this reaction, and where carbo-cations are being formed. Any help would be great. Thanks.
 
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What would you expect to happen in the first step, when HBr is added?
 
PhaseShifter said:
What would you expect to happen in the first step, when HBr is added?

Well The H would attack the double bonds and form the most stable carbo-cation?
 
Correct. So what remains is determining whether the ends of each double bond are primary, secondary, or tertiary carbons to determine the relative stabilities of carbocations.

Once you know where the hydrogen and bromine go, you move on to the second step, which is a nucleophilic substitution using methoxide ions.
 
PhaseShifter said:
Correct. So what remains is determining whether the ends of each double bond are primary, secondary, or tertiary carbons to determine the relative stabilities of carbocations.

Once you know where the hydrogen and bromine go, you move on to the second step, which is a nucleophilic substitution using methoxide ions.

Thanks for the help, I understand the first step and where the bromine's attach to. What exactly is happening in the second step with the methoxide ions?
 
Nucleophilic substitution.
 

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