Benzyl alcohol and methyl benzoate (shown below) are dissolved in an ether solution. Choose the best process to separate the following two compounds using an acid-base extraction. benzyl alcohol OH d OCH3 methyl benzoate A) Add aqueous NaOH and extract the benzyl alcohol into the aqueous layer. B) Add aqueous NaHCO3 and extract the benzyl alcohol into the aqueous layer. C) Add aqueous NaOH and extract the methyl benzoate into the aqueous layer. D) Add aqueous HCI and extract the benzyl alcohol into the aqueous layer.

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**Separation of Benzyl Alcohol and Methyl Benzoate using Acid-Base Extraction**

**Problem Statement:**

Benzyl alcohol and methyl benzoate (shown below) are dissolved in an ether solution. Choose the best process to separate the following two compounds using an acid-base extraction.

**Chemical Structures:**

1. **Benzyl Alcohol**:
   - Structure:
     ![Benzyl Alcohol](https://upload.wikimedia.org/wikipedia/commons/7/7a/Benzyl_alcohol.svg)
     - Benzyl alcohol has a hydroxyl group (-OH) attached to a benzyl ring.

2. **Methyl Benzoate**:
   - Structure:
     ![Methyl Benzoate](https://upload.wikimedia.org/wikipedia/commons/7/7e/Methyl_benzoate.svg)
     - Methyl benzoate has an ester functional group (-COOCH3) attached to a benzene ring.

**Options for Separation:**

A) Add aqueous NaOH and extract the benzyl alcohol into the aqueous layer.

B) Add aqueous NaHCO₃ and extract the benzyl alcohol into the aqueous layer.

C) Add aqueous NaOH and extract the methyl benzoate into the aqueous layer.

D) Add aqueous HCl and extract the benzyl alcohol into the aqueous layer.

E) These two compounds cannot be separated using an acid-base extraction.

**Explanation:**

To separate these compounds, one must consider the functional groups present in benzyl alcohol and methyl benzoate and how they react to acid and base solutions:

1. **Benzyl Alcohol**:
   - It contains a hydroxyl group (-OH) but is not acidic enough to react with bicarbonate (NaHCO₃) or to form salts with NaOH.

2. **Methyl Benzoate**:
   - It is neutral and does not react with either NaOH or NaHCO₃.

Given these properties:
- By adding NaOH, neither compound would dissolve as a salt in the aqueous layer since neither benzyl alcohol nor methyl benzoate react with NaOH to form salts.
- NaHCO₃ addition will similarly not dissolve either as they do not react under these conditions.
- Using HCl will also not selectively dissolve the benzyl alcohol and separate it from methyl benzoate.

Therefore, the correct answer must reflect that these two compounds cannot be separated using the given acid
Transcribed Image Text:**Separation of Benzyl Alcohol and Methyl Benzoate using Acid-Base Extraction** **Problem Statement:** Benzyl alcohol and methyl benzoate (shown below) are dissolved in an ether solution. Choose the best process to separate the following two compounds using an acid-base extraction. **Chemical Structures:** 1. **Benzyl Alcohol**: - Structure: ![Benzyl Alcohol](https://upload.wikimedia.org/wikipedia/commons/7/7a/Benzyl_alcohol.svg) - Benzyl alcohol has a hydroxyl group (-OH) attached to a benzyl ring. 2. **Methyl Benzoate**: - Structure: ![Methyl Benzoate](https://upload.wikimedia.org/wikipedia/commons/7/7e/Methyl_benzoate.svg) - Methyl benzoate has an ester functional group (-COOCH3) attached to a benzene ring. **Options for Separation:** A) Add aqueous NaOH and extract the benzyl alcohol into the aqueous layer. B) Add aqueous NaHCO₃ and extract the benzyl alcohol into the aqueous layer. C) Add aqueous NaOH and extract the methyl benzoate into the aqueous layer. D) Add aqueous HCl and extract the benzyl alcohol into the aqueous layer. E) These two compounds cannot be separated using an acid-base extraction. **Explanation:** To separate these compounds, one must consider the functional groups present in benzyl alcohol and methyl benzoate and how they react to acid and base solutions: 1. **Benzyl Alcohol**: - It contains a hydroxyl group (-OH) but is not acidic enough to react with bicarbonate (NaHCO₃) or to form salts with NaOH. 2. **Methyl Benzoate**: - It is neutral and does not react with either NaOH or NaHCO₃. Given these properties: - By adding NaOH, neither compound would dissolve as a salt in the aqueous layer since neither benzyl alcohol nor methyl benzoate react with NaOH to form salts. - NaHCO₃ addition will similarly not dissolve either as they do not react under these conditions. - Using HCl will also not selectively dissolve the benzyl alcohol and separate it from methyl benzoate. Therefore, the correct answer must reflect that these two compounds cannot be separated using the given acid
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