For each reaction below, look at the reagents and conditions (above and below the arrow) and determine the final product. Indicate if the reaction proceeds via either: SN1 mechanism, SN2 mechanism, other mechanism, or the reaction cannot take place (NO REACTION). O A OB O C OD ..O HS: DMF A: B: C: D: ? : SH :CI SH NO REACTION : SH (SN 1 mechanism) (Nucleophilic Addition mechanism) (SN2 mechanism)

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For each reaction below, look at the reagents and conditions (above and below the arrow) and determine the final product.

Indicate if the reaction proceeds via either: S<sub>N</sub>1 mechanism, S<sub>N</sub>2 mechanism, other mechanism, or the reaction cannot take place (NO REACTION).

**Reaction Scheme:**

- **Reagents/Conditions:**
  - Starting compound: a secondary alkyl chloride
  - Nucleophile: HS<sup>−</sup> 
  - Solvent: DMF

- **Possible Products and Mechanisms:**
  - **A:** Compound with SH replacing Cl on the secondary carbon (S<sub>N</sub>1 mechanism)
  - **B:** Compound with SH and Cl on adjacent carbons (Nucleophilic Addition mechanism)
  - **C:** NO REACTION
  - **D:** Compound with SH replacing Cl on the secondary carbon (S<sub>N</sub>2 mechanism)

**Question:**
Select one of the following options:
- ○ A
- ○ B
- ○ C
- ○ D

**Explanation of Options:**
- **A (S<sub>N</sub>1 mechanism):** Proceeds via a two-step mechanism involving the formation of a carbocation intermediate, typically in polar protic solvents.
- **B (Nucleophilic Addition mechanism):** Suggests simultaneous attachment of both nucleophile and leaving group, which is not typical for halides like Cl.
- **C (NO REACTION):** Indicates that under given conditions, no reaction occurs.
- **D (S<sub>N</sub>2 mechanism):** Proceeds via a one-step mechanism with nucleophilic attack and leaving group departure, typically in polar aprotic solvents like DMF.

The correct choice should be based on understanding these mechanisms and the conditions provided.
Transcribed Image Text:For each reaction below, look at the reagents and conditions (above and below the arrow) and determine the final product. Indicate if the reaction proceeds via either: S<sub>N</sub>1 mechanism, S<sub>N</sub>2 mechanism, other mechanism, or the reaction cannot take place (NO REACTION). **Reaction Scheme:** - **Reagents/Conditions:** - Starting compound: a secondary alkyl chloride - Nucleophile: HS<sup>−</sup> - Solvent: DMF - **Possible Products and Mechanisms:** - **A:** Compound with SH replacing Cl on the secondary carbon (S<sub>N</sub>1 mechanism) - **B:** Compound with SH and Cl on adjacent carbons (Nucleophilic Addition mechanism) - **C:** NO REACTION - **D:** Compound with SH replacing Cl on the secondary carbon (S<sub>N</sub>2 mechanism) **Question:** Select one of the following options: - ○ A - ○ B - ○ C - ○ D **Explanation of Options:** - **A (S<sub>N</sub>1 mechanism):** Proceeds via a two-step mechanism involving the formation of a carbocation intermediate, typically in polar protic solvents. - **B (Nucleophilic Addition mechanism):** Suggests simultaneous attachment of both nucleophile and leaving group, which is not typical for halides like Cl. - **C (NO REACTION):** Indicates that under given conditions, no reaction occurs. - **D (S<sub>N</sub>2 mechanism):** Proceeds via a one-step mechanism with nucleophilic attack and leaving group departure, typically in polar aprotic solvents like DMF. The correct choice should be based on understanding these mechanisms and the conditions provided.
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