Addition reaction to produce 3-methyl-3-hexanol

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Discussion Overview

The discussion revolves around the addition reaction to produce 3-methyl-3-hexanol from 3-methyl-3-hexene, focusing on the mechanisms involved in the reaction and the roles of different species in the addition process. The scope includes homework-related inquiries and conceptual clarifications regarding organic chemistry mechanisms.

Discussion Character

  • Homework-related
  • Conceptual clarification
  • Technical explanation
  • Exploratory

Main Points Raised

  • One participant requests a chemical equation for the addition reaction to produce 3-methyl-3-hexanol and expresses confusion about the process.
  • Another participant asks for a mechanism of the initial addition steps, indicating a need for a visual representation.
  • A participant suggests that adding water (HOH) to 3-methyl-3-hexene involves adding the hydrogen atom to a carbon with more hydrogens, but is uncertain about which carbon this refers to.
  • There is a discussion about whether the species adding to alkenes is nucleophilic or electrophilic, with one participant asserting it is electrophilic.
  • Participants explore which part of water (H2O) would attack the double bond, with one suggesting that the hydrogen would attack due to its positive charge.
  • Questions arise about how the addition of water changes the alkene species, specifically whether it results in a single bond instead of a double bond.
  • One participant introduces the concept of charged species resulting from the addition of a charged species like H+, prompting further inquiry into the nature of the resulting charged species.

Areas of Agreement / Disagreement

Participants express uncertainty about specific details of the reaction mechanism and the roles of different species, indicating that there is no consensus on the exact steps or outcomes of the addition reaction.

Contextual Notes

Participants are working through the complexities of organic reaction mechanisms, including the roles of electrophiles and nucleophiles, and the implications of charge distribution during the reaction. There are unresolved questions regarding the specifics of the addition process and the resulting species.

Specter

Homework Statement


Write a chemical equation for addition reactions to produce 3-methyl-3-hexanol.
Condensed structural formulas should be used for each organic compound.

Homework Equations


none

The Attempt at a Solution


https://i.imgur.com/REIpKHK.jpg

REIpKHK.jpg


Is this correct? My friend tried explaining this to me but I still don't really understand it. I would like to practice some on my own but I can't find anything online explaining how to do it in the first place. Any help would be appreciated, thanks!
 

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Can you draw out a mechanism for how you think the initial addition steps will take place?
 
TeethWhitener said:
Can you draw out a mechanism for how you think the initial addition steps will take place?
Hey, sorry for the late response.

So to get 3-methyl-3-hexanol I must add HOH to 3-methyl-3-hexene.

In my lesson I am told that the hydrogen atom of water would be added to the carbon that already has more hydrogens. I'm not sure if that means the hydrogen atom would be added to the CH2 to the left of the central carbon, or if it would be added to the CH to the right of the central carbon where the double bond is (if this doesn't make sense I can try to draw it out). I am also told that the OH of water would be added to the central carbon atom, which I did.
 
Let’s tackle the issues one at a time. What type of species adds to alkenes? Nucleophilic (partially negatively charged) or electrophilic (partially positively charged)?
 
TeethWhitener said:
Let’s tackle the issues one at a time. What type of species adds to alkenes? Nucleophilic (partially negatively charged) or electrophilic (partially positively charged)?
Electrophilic
 
Ok so if you are adding H2O, which part will attack the double bond?
 
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TeethWhitener said:
Ok so if you are adding H2O, which part will attack the double bond?
Hydrogen would attack the double bond because it is positive.
 
And how would this change the alkene species?
 
TeethWhitener said:
And how would this change the alkene species?
Does it become a single bond instead of a double bond?
 
  • #10
Consider a generic alkene: R2C=CR2 (doesn’t have to be symmetric). If you add a charged species like H+, you have to end up with a charged species, right? What does that charged species look like? (What element in the alkene ends up with the charge, If you were to do arrow pushing?)
 

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