Substitution reaction and configuration

In summary, the question asks for the product of a reaction between (2S,3S)-2-chloro-3-methylpentane and a high concentration of CH3O-. The student's attempted solution involves replacing the -Cl with -OCH3 and taking into account the two asymmetric centers in the original compound. They are unsure if the product will have a 2R or 2S configuration, and questions whether the reaction will result in an Sn2 or E2 product.
  • #1
Thecoolone
1
0

Homework Statement



(2S,3S)-2-chloro-3-methylpentane + high concentration of CH3O- ---> ?


The Attempt at a Solution



I need to find the product and usually my method is to knock off the -Cl replacing it by
-OCH3 and when drawing the compound I just make an mirror image. In (2S,3S)-2-chloro-3-methylpentane there are two asymmetric centers and for the product with Cl replaced with OCH3 I assume that it changes configuration so that it becomes 2R instead of 2S. My problem is now, that I cannot draw the product without getting (2R,3R).
Is this correct? I assume that it should be 2R,3S because I do not knock off any atom or molecule from the second asymmetric center.
 
Physics news on Phys.org
  • #2
It is a secondary halide adjacent a tertiary carbon center. You sure you're going to get Sn2 product? How about E2?
 

1. What is a substitution reaction?

A substitution reaction is a type of chemical reaction in which one atom or group of atoms is replaced by another atom or group of atoms. This can occur in organic and inorganic compounds.

2. What is the difference between nucleophilic and electrophilic substitution reactions?

In a nucleophilic substitution reaction, a nucleophile (an atom or group of atoms with a lone pair of electrons) replaces a leaving group in an organic compound. In an electrophilic substitution reaction, an electrophile (an atom or group of atoms that is electron-deficient) replaces a hydrogen atom in an aromatic compound.

3. How does the configuration of a molecule affect its reactivity in a substitution reaction?

The configuration of a molecule refers to the arrangement of its atoms in space. This can affect the accessibility of certain atoms or functional groups, which can in turn impact the reactivity of the molecule in a substitution reaction. For example, a molecule with a bulky configuration may be less reactive than a molecule with a more open configuration.

4. What factors influence the rate of a substitution reaction?

The rate of a substitution reaction can be influenced by a variety of factors, including the nature of the substituent and the solvent, the concentration of the reactants, and the temperature. Additionally, the type of substitution reaction (e.g. nucleophilic or electrophilic) can also affect the rate.

5. Can a substitution reaction result in the formation of multiple products?

Yes, a substitution reaction can result in the formation of multiple products, especially in cases where there are multiple possible sites for substitution. This can also occur if the reactants have different reactivities towards substitution, leading to the formation of different products depending on the reaction conditions.

Similar threads

SN2 Substitution Products: (2R, 3S)-3-methyl-2-methoxypentane
    • Biology and Chemistry Homework Help
Replies
7
Views
5K
Naming of Haloalkane (Disputed)
    • Biology and Chemistry Homework Help
Replies
2
Views
3K
Electrophilic Aromatic Substitution
    • Biology and Chemistry Homework Help
Replies
2
Views
1K
Why Does C6H5CH(Cl)CH3 < (CH3)3 CCl < C6H5C(CH3)2 Cl Undergo SN1 Reaction?
    • Biology and Chemistry Homework Help
Replies
1
Views
1K
Organic Chemistry - Elimination/substitution
    • Biology and Chemistry Homework Help
Replies
1
Views
3K
Decomposition of N2O5: Reaction Mechanisms and Intermediate Concentrations
    • Biology and Chemistry Homework Help
Replies
1
Views
3K
OChem Tosylation Reaction: Predicting Major Product with p-TsOH Catalyst
    • Biology and Chemistry Homework Help
Replies
5
Views
1K
I Proving Gauss' Law using a Cubical Surface
    • Classical Physics
Replies
5
Views
2K
Lewis Reaction Questions (Organic Chemistry)
    • Biology and Chemistry Homework Help
Replies
2
Views
5K
Chemistry: Not a Friedel-Crafts Reaction
    • Biology and Chemistry Homework Help
Replies
2
Views
2K

Hot Threads

Recent Insights

Back
Top