H3CS.. Draw the full mechanism to show how this product was made. You must show all the steps and arrows. MXX bo cibers CH3S H₂0 SCH3 Vingylo Avoitong or Teas& Wignon + CL Solidgoolou 100%\book)

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**Title: Understanding the Reaction Mechanism of Alkyl Chloride with Methanethiolate**

**Introduction:**

In this module, we will explore the detailed mechanism by which an alkyl chloride reacts with methanethiolate ions to form thioethers. This reaction serves as an excellent example of nucleophilic substitution.

**Reaction Overview:**

1. **Starting Material:**
   - The reactant is a secondary alkyl chloride, depicted with a chlorine (Cl) atom attached to a carbon in the molecule.
   
2. **Reagent:**
   - The nucleophile in this reaction is the methanethiolate ion (\(CH_3S^-\)), often supplied as a salt like sodium methanethiolate.
   - The reaction occurs in aqueous medium (\(H_2O\)).

3. **Products:**
   - The main product is a thioether, where the chlorine has been substituted by a sulfur group (\(SCH_3\)).
   - The side product includes another stereoisomer of the thioether with a reversed configuration (\(H_3CS\)).
   - Chloride ion (\(Cl^-\)) is released as a by-product.

**Mechanism Explanation:**

- **Nucleophilic Attack:**
  - The methanethiolate ion (\(CH_3S^-\)), being a strong nucleophile, approaches the carbon atom bonded to the chlorine (Cl) from the opposite side. 
  - This results in a backside attack, which is typical for SN2 reactions, leading to the inversion of configuration at this carbon center.

- **Transition State:**
  - During this process, a transition state is formed where the carbon is partially bonded to both the sulfur and chlorine atoms.

- **Displacement:**
  - The chlorine atom is displaced, resulting in the formation of a new carbon-sulfur (C-S) bond and the cleavage of the carbon-chlorine (C-Cl) bond.

- **Products Formation:**
  - Two stereoisomers of the thioether are produced due to the inversion of configuration at the chiral center.
  - Chloride ion (\(Cl^-\)) is released into the solution.

**Conclusion:**

Understanding the mechanism of this reaction provides insight into nucleophilic substitution processes, particularly the SN2 mechanism, which involves a single concerted step with inversion of configuration. This knowledge is fundamental in synthetic organic chemistry for designing reactions that involve halides and
Transcribed Image Text:**Title: Understanding the Reaction Mechanism of Alkyl Chloride with Methanethiolate** **Introduction:** In this module, we will explore the detailed mechanism by which an alkyl chloride reacts with methanethiolate ions to form thioethers. This reaction serves as an excellent example of nucleophilic substitution. **Reaction Overview:** 1. **Starting Material:** - The reactant is a secondary alkyl chloride, depicted with a chlorine (Cl) atom attached to a carbon in the molecule. 2. **Reagent:** - The nucleophile in this reaction is the methanethiolate ion (\(CH_3S^-\)), often supplied as a salt like sodium methanethiolate. - The reaction occurs in aqueous medium (\(H_2O\)). 3. **Products:** - The main product is a thioether, where the chlorine has been substituted by a sulfur group (\(SCH_3\)). - The side product includes another stereoisomer of the thioether with a reversed configuration (\(H_3CS\)). - Chloride ion (\(Cl^-\)) is released as a by-product. **Mechanism Explanation:** - **Nucleophilic Attack:** - The methanethiolate ion (\(CH_3S^-\)), being a strong nucleophile, approaches the carbon atom bonded to the chlorine (Cl) from the opposite side. - This results in a backside attack, which is typical for SN2 reactions, leading to the inversion of configuration at this carbon center. - **Transition State:** - During this process, a transition state is formed where the carbon is partially bonded to both the sulfur and chlorine atoms. - **Displacement:** - The chlorine atom is displaced, resulting in the formation of a new carbon-sulfur (C-S) bond and the cleavage of the carbon-chlorine (C-Cl) bond. - **Products Formation:** - Two stereoisomers of the thioether are produced due to the inversion of configuration at the chiral center. - Chloride ion (\(Cl^-\)) is released into the solution. **Conclusion:** Understanding the mechanism of this reaction provides insight into nucleophilic substitution processes, particularly the SN2 mechanism, which involves a single concerted step with inversion of configuration. This knowledge is fundamental in synthetic organic chemistry for designing reactions that involve halides and
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