SN2 Substitution Products: (2R, 3S)-3-methyl-2-methoxypentane

  • Thread starter assaftolko
  • Start date
  • Tags
    Reaction
In summary, in the SN2 reaction of (2S, 3S)-2-chloro-3-methylpentane with CH3O-, the configuration of the carbon attached to Cl changes, resulting in (2R, 3S)-3-methyl-2-methoxypentane as the substitution product. This is due to the Williamson ether synthesis reaction, where the nucleophile attacks the carbon, causing inversion of configuration and forming an ether.
  • #1
assaftolko
171
0

Homework Statement



Find the substitution products of ( 2S, 3S)-2-chloro-3-methylpentane + CH3O- in SN2 reaction.





The Attempt at a Solution



Will the anti-attack of the nucleophile result in the change of S to R for both the chiral carbons or just for the one with Cl connected to it? How can I know this?
 
Physics news on Phys.org
  • #2
assaftolko said:

Homework Statement



Find the substitution products of ( 2S, 3S)-2-chloro-3-methylpentane + CH3O- in SN2 reaction.





The Attempt at a Solution



Will the anti-attack of the nucleophile result in the change of S to R for both the chiral carbons or just for the one with Cl connected to it? How can I know this?

The configuration of the carbon attached with Cl changes. The configuration changes only when the bonds to the chiral carbon break or change.
 
  • #3
So I'll get (2R,3S)-3-methyl-2-pentanol?
 
  • #4
assaftolko said:
So I'll get (2R,3S)-3-methyl-2-pentanol?

How do you get an alcohol? Shouldn't that be an ether?
 
  • #5
How can it be ether? Cl is the leaving group and you get OH that is attached to the Cl's carbon from the other side. Now This carbon is directly attached to O, H, R and R', I don't see how the oxygen can be attached to 2 carbons to form ether...
 
  • #6
assaftolko said:
How can it be ether? Cl is the leaving group and you get OH that is attached to the Cl's carbon from the other side. Now This carbon is directly attached to O, H, R and R', I don't see how the oxygen can be attached to 2 carbons to form ether...

Williamson ether synthesis.
 
  • #7
  • #8
assaftolko said:
How can it be ether? Cl is the leaving group and you get OH that is attached to the Cl's carbon from the other side. Now This carbon is directly attached to O, H, R and R', I don't see how the oxygen can be attached to 2 carbons to form ether...

You said in your first post that the nucleophile was CH3O-, not OH-. This would account for a carbon on one side of the oxygen. As this nucleophile attacks, it kicks away a Cl-, causing inversion of configuration and a new bond to carbon. That makes the oxygen bridge two carbons, forming an ether. I believe the correct answer would be (2R, 3S)-3-methyl-2-methoxypentane.
 
Last edited:

1. What are the products of an SN2 reaction?

The products of an SN2 (substitution nucleophilic bimolecular) reaction are a nucleophile and a substituted molecule.

2. How is the stereochemistry affected in an SN2 reaction?

In an SN2 reaction, the stereochemistry of the product is inverted, meaning the original configuration of the molecule is flipped.

3. What factors influence the rate of an SN2 reaction?

The rate of an SN2 reaction is influenced by the strength of the nucleophile, the strength of the leaving group, and the steric hindrance around the carbon atom where the substitution occurs.

4. What is the difference between an SN1 and SN2 reaction?

The main difference between an SN1 and SN2 reaction is the mechanism. An SN1 reaction proceeds through a carbocation intermediate and is a first-order reaction, while an SN2 reaction is a one-step process and is a second-order reaction.

5. What are some common examples of SN2 reactions?

Some common examples of SN2 reactions include the substitution of a halide with a nucleophile, such as the conversion of an alkyl halide to an alcohol or ether, and the synthesis of esters from carboxylic acids and alcohols.

Similar threads

  • Biology and Chemistry Homework Help
Replies
1
Views
2K
  • Biology and Chemistry Homework Help
Replies
1
Views
3K
  • Biology and Chemistry Homework Help
Replies
28
Views
4K
Replies
5
Views
3K
  • Biology and Chemistry Homework Help
Replies
2
Views
2K
  • Biology and Chemistry Homework Help
Replies
1
Views
5K
  • Biology and Chemistry Homework Help
Replies
1
Views
6K
Replies
1
Views
826
Replies
4
Views
2K
  • Biology and Chemistry Homework Help
Replies
4
Views
7K
Back
Top