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500 mL of water and 500 mL of dichloromethane (d = 1.3 g/mL) are added to a mixture containing benzoic acid, cresol, methoxyethane, and N-methylethanamine. Four solutions are available for extraction of the mixture: HCN, HCl, NaOH, and LiHCO3. After the initial wash, the top layer from each extraction was retained and one of the preceding solutions was added. Which of the following statements most accurately describes this procedure?
  • a)
    After washing with LiHCO3 and then NaOH, only N-methylethanamine and methoxyethane remain in the separatory funnel.
  • b)
    Methoxyethane will only be extracted upon protonation into a carbocation.
  • c)
    Benzoic acid can be extracted and isolated with either LiHCO3 or NaOH.
  • d)
    Cresol must be extracted first with a strong mineral acid such as HCl.
Correct answer is option 'C'. Can you explain this answer?
Most Upvoted Answer
500 mL of water and 500 mL of dichloromethane (d = 1.3 g/mL) are added...
Cresol is like phenol, but with an extra methyl group at the para position. Due to its alcohol functional group, it is considered a weak acid and would only be extracted with the stronger base. With base extraction, consider the strength of the acid before picking the base.
Methoxyethane is an ether. While ethers can get protonated, the carbocation is only an intermediate and is of transient existence. It will remain in the organic layer once all the other 3 compounds are extracted.
N-methylethanamine is a base due to its amine group, and amines are best extracted by a strong acid.
Since we are retaining the top layer of each extraction, after the first wash, we have benzoic acid in the aqueous layer, which is the top layer. If we wash this layer with NaOH, we would have benzoate ion in the aqueous layer. No further separation is possible.
Benzoic acid can be extracted and isolated with either a weak or strong base, but if in a mixture with an alcohol, it should be extracted first with a weak base like LiHCO3 and the alcohol extracted a strong base like Na2s
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Community Answer
500 mL of water and 500 mL of dichloromethane (d = 1.3 g/mL) are added...
Explanation:

Benzoic Acid Extraction:
- Benzoic acid can be extracted and isolated with either LiHCO3 or NaOH.
- Both LiHCO3 and NaOH solutions are basic and will ionize the benzoic acid into its conjugate base form, making it soluble in the aqueous layer and allowing for extraction.

Methoxyethane Extraction:
- Methoxyethane will not only be extracted upon protonation into a carbocation.
- Methoxyethane is a neutral compound and will partition between the aqueous and organic layers based on its solubility in each solvent.

Cresol Extraction:
- Cresol does not need to be extracted first with a strong mineral acid such as HCl.
- Cresol is typically more soluble in basic solutions, so it can be extracted using either LiHCO3 or NaOH.
Therefore, the most accurate statement is that benzoic acid can be extracted and isolated with either LiHCO3 or NaOH.
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500 mL of water and 500 mL of dichloromethane (d = 1.3 g/mL) are added to a mixture containing benzoic acid, cresol, methoxyethane, and N-methylethanamine. Four solutions are available for extraction of the mixture: HCN, HCl, NaOH, and LiHCO3. After the initial wash, the top layer from each extraction was retained and one of the preceding solutions was added. Which of the following statements most accurately describes this procedure?a)After washing with LiHCO3 and then NaOH, only N-methylethanamine and methoxyethane remain in the separatory funnel.b)Methoxyethane will only be extracted upon protonation into a carbocation.c)Benzoic acid can be extracted and isolated with either LiHCO3 or NaOH.d)Cresol must be extracted first with a strong mineral acid such as HCl.Correct answer is option 'C'. Can you explain this answer?
Question Description
500 mL of water and 500 mL of dichloromethane (d = 1.3 g/mL) are added to a mixture containing benzoic acid, cresol, methoxyethane, and N-methylethanamine. Four solutions are available for extraction of the mixture: HCN, HCl, NaOH, and LiHCO3. After the initial wash, the top layer from each extraction was retained and one of the preceding solutions was added. Which of the following statements most accurately describes this procedure?a)After washing with LiHCO3 and then NaOH, only N-methylethanamine and methoxyethane remain in the separatory funnel.b)Methoxyethane will only be extracted upon protonation into a carbocation.c)Benzoic acid can be extracted and isolated with either LiHCO3 or NaOH.d)Cresol must be extracted first with a strong mineral acid such as HCl.Correct answer is option 'C'. Can you explain this answer? for MCAT 2024 is part of MCAT preparation. The Question and answers have been prepared according to the MCAT exam syllabus. Information about 500 mL of water and 500 mL of dichloromethane (d = 1.3 g/mL) are added to a mixture containing benzoic acid, cresol, methoxyethane, and N-methylethanamine. Four solutions are available for extraction of the mixture: HCN, HCl, NaOH, and LiHCO3. After the initial wash, the top layer from each extraction was retained and one of the preceding solutions was added. Which of the following statements most accurately describes this procedure?a)After washing with LiHCO3 and then NaOH, only N-methylethanamine and methoxyethane remain in the separatory funnel.b)Methoxyethane will only be extracted upon protonation into a carbocation.c)Benzoic acid can be extracted and isolated with either LiHCO3 or NaOH.d)Cresol must be extracted first with a strong mineral acid such as HCl.Correct answer is option 'C'. Can you explain this answer? covers all topics & solutions for MCAT 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for 500 mL of water and 500 mL of dichloromethane (d = 1.3 g/mL) are added to a mixture containing benzoic acid, cresol, methoxyethane, and N-methylethanamine. Four solutions are available for extraction of the mixture: HCN, HCl, NaOH, and LiHCO3. After the initial wash, the top layer from each extraction was retained and one of the preceding solutions was added. Which of the following statements most accurately describes this procedure?a)After washing with LiHCO3 and then NaOH, only N-methylethanamine and methoxyethane remain in the separatory funnel.b)Methoxyethane will only be extracted upon protonation into a carbocation.c)Benzoic acid can be extracted and isolated with either LiHCO3 or NaOH.d)Cresol must be extracted first with a strong mineral acid such as HCl.Correct answer is option 'C'. Can you explain this answer?.
Solutions for 500 mL of water and 500 mL of dichloromethane (d = 1.3 g/mL) are added to a mixture containing benzoic acid, cresol, methoxyethane, and N-methylethanamine. Four solutions are available for extraction of the mixture: HCN, HCl, NaOH, and LiHCO3. After the initial wash, the top layer from each extraction was retained and one of the preceding solutions was added. Which of the following statements most accurately describes this procedure?a)After washing with LiHCO3 and then NaOH, only N-methylethanamine and methoxyethane remain in the separatory funnel.b)Methoxyethane will only be extracted upon protonation into a carbocation.c)Benzoic acid can be extracted and isolated with either LiHCO3 or NaOH.d)Cresol must be extracted first with a strong mineral acid such as HCl.Correct answer is option 'C'. Can you explain this answer? in English & in Hindi are available as part of our courses for MCAT. Download more important topics, notes, lectures and mock test series for MCAT Exam by signing up for free.
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