This is a lab for sn2 nucleophilic substitution preparation of nerolin.   Write the balanced chemical equation for this reaction.

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This is a lab for sn2 nucleophilic substitution preparation of nerolin.  

Write the balanced chemical equation for this reaction.

 

### Synthesis of Nerolin

#### Reaction Mechanism

The chemical reaction depicted involves the use of **potassium hydroxide (KOH)** as a base. It acts to deprotonate the slightly acidic phenolic proton of **2-naphthol**. This results in the formation of **2-naphthoxide**, which serves as a nucleophile. The 2-naphthoxide then attacks **iodoethane**, displacing the iodide ion. The reaction proceeds via an **S<sub>N</sub>2 bimolecular mechanism**, where the rate is dependent on the concentrations of both the 2-naphthol and the iodoethane.

#### Reaction Equations

1. 2-Naphthol is treated with iodoethane in the presence of potassium hydroxide:
   - ![2-Naphthol + Iodoethane + KOH](example-structure)
   - **Product Formation:** 2-Naphthoxyethane + KI + H<sub>2</sub>O

2. The nucleophilic attack by 2-naphthoxide on iodoethane:
   - ![2-Naphthoxide + Iodoethane](example-structure)
   - **Products:** 2-Naphthoxyethane + Iodide Ion

#### Solubility Considerations

One critical aspect of this synthesis is the solubility of the reactants. Strong bases typically have low solubility in organic solvents, which are necessary for the reaction. Potassium hydroxide is chosen over sodium hydroxide due to its higher solubility in ethanol. Ethanol acts as a suitable solvent for these reactions. The product, nerolin, has low solubility in ethanol, leading to its precipitation upon reaction completion. The crude product can then be purified by recrystallization from a mixture of alcohol and water.

This synthesis highlights important aspects of reaction mechanism, kinetics, and solubility, all of which play crucial roles in organic chemistry.
Transcribed Image Text:### Synthesis of Nerolin #### Reaction Mechanism The chemical reaction depicted involves the use of **potassium hydroxide (KOH)** as a base. It acts to deprotonate the slightly acidic phenolic proton of **2-naphthol**. This results in the formation of **2-naphthoxide**, which serves as a nucleophile. The 2-naphthoxide then attacks **iodoethane**, displacing the iodide ion. The reaction proceeds via an **S<sub>N</sub>2 bimolecular mechanism**, where the rate is dependent on the concentrations of both the 2-naphthol and the iodoethane. #### Reaction Equations 1. 2-Naphthol is treated with iodoethane in the presence of potassium hydroxide: - ![2-Naphthol + Iodoethane + KOH](example-structure) - **Product Formation:** 2-Naphthoxyethane + KI + H<sub>2</sub>O 2. The nucleophilic attack by 2-naphthoxide on iodoethane: - ![2-Naphthoxide + Iodoethane](example-structure) - **Products:** 2-Naphthoxyethane + Iodide Ion #### Solubility Considerations One critical aspect of this synthesis is the solubility of the reactants. Strong bases typically have low solubility in organic solvents, which are necessary for the reaction. Potassium hydroxide is chosen over sodium hydroxide due to its higher solubility in ethanol. Ethanol acts as a suitable solvent for these reactions. The product, nerolin, has low solubility in ethanol, leading to its precipitation upon reaction completion. The crude product can then be purified by recrystallization from a mixture of alcohol and water. This synthesis highlights important aspects of reaction mechanism, kinetics, and solubility, all of which play crucial roles in organic chemistry.
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