Addition reaction to produce 3-methyl-3-hexanol

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SUMMARY

The discussion centers on the addition reaction to produce 3-methyl-3-hexanol from 3-methyl-3-hexene through the hydration process. The reaction involves adding water (HOH) across the double bond of the alkene, where the hydrogen atom attaches to the carbon with more hydrogens, and the hydroxyl (OH) group attaches to the central carbon. Participants clarify that the electrophilic addition mechanism is key, with the hydrogen from water acting as the electrophile that attacks the double bond, resulting in a single bond formation.

PREREQUISITES
  • Understanding of electrophilic addition reactions
  • Familiarity with alkenes and their reactivity
  • Knowledge of nucleophiles and electrophiles in organic chemistry
  • Ability to interpret and draw chemical mechanisms
NEXT STEPS
  • Study the mechanism of electrophilic addition reactions in alkenes
  • Learn about Markovnikov's rule in hydration reactions
  • Explore the concept of carbocation stability and rearrangements
  • Practice drawing reaction mechanisms for various alkene hydration scenarios
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Chemistry students, organic chemists, and educators looking to deepen their understanding of addition reactions and mechanisms in organic synthesis.

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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