3. The sequence for separating a solution of benzoic acid, naphthalene and 2-naphthol via extraction starts by washing the solution with aqueous sodium bicarbonate and follows with washing the resulting organic extract with aqueous sodium hydroxide. Why are the aqueous bases used in this order rather than the reverse order? Provide drawings and a brief explanation. The information below might be useful. OH Benzoic acid pka= 4.20 Base NaHCO3 NaOH 2-naphthol pka= 9.5 OH Conjugate Acid H₂CO3 H₂O naphthalene pka 6.4 16 |
3. The sequence for separating a solution of benzoic acid, naphthalene and 2-naphthol via extraction starts by washing the solution with aqueous sodium bicarbonate and follows with washing the resulting organic extract with aqueous sodium hydroxide. Why are the aqueous bases used in this order rather than the reverse order? Provide drawings and a brief explanation. The information below might be useful. OH Benzoic acid pka= 4.20 Base NaHCO3 NaOH 2-naphthol pka= 9.5 OH Conjugate Acid H₂CO3 H₂O naphthalene pka 6.4 16 |
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter23: Amines
Section: Chapter Questions
Problem 23.32P: Suppose you have a mixture of these three compounds. Devise a chemical procedure based on their...
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![3. The sequence for separating a solution of benzoic acid, naphthalene and 2-naphthol
via extraction starts by washing the solution with aqueous sodium bicarbonate and follows
with washing the resulting organic extract with aqueous sodium hydroxide. Why are the
aqueous bases used in this order rather than the reverse order? Provide drawings and a brief
explanation. The information below might be useful.
OH
Benzoic acid
pka= 4.20
Base
NaHCO3
NaOH
OH
2-naphthol
pka= 9.5
Conjugate Acid
H₂CO3
H₂O
naphthalene
pka
6.4
16
1](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8dec9dd7-700d-4afc-ae01-f086f51bf27f%2F69a57eaa-9e85-4142-8c21-c9a446d2772c%2Fhte2g1l_processed.png&w=3840&q=75)
Transcribed Image Text:3. The sequence for separating a solution of benzoic acid, naphthalene and 2-naphthol
via extraction starts by washing the solution with aqueous sodium bicarbonate and follows
with washing the resulting organic extract with aqueous sodium hydroxide. Why are the
aqueous bases used in this order rather than the reverse order? Provide drawings and a brief
explanation. The information below might be useful.
OH
Benzoic acid
pka= 4.20
Base
NaHCO3
NaOH
OH
2-naphthol
pka= 9.5
Conjugate Acid
H₂CO3
H₂O
naphthalene
pka
6.4
16
1
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