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...

See similar textbooks

Similar questions

A mixture of compounds is dissolved in ether, and extracted with 10% NaHCO3 solution. The aqueous extract is treated with 6M HCI solution, and extracted with dichloromethane. If the mixture contains a carboxylic acid, where is it? The bottom layer of the second extraction The top layer of the first extraction The top layer of the second extraction () The bottom layer of the first extraction
How to separate phenol from a mixture of benzoic acid and phenol by extraction?
What generalization trends may be extracted from the following series in terms of solubility with (a) NaOH, (b) NaHCO3 (c) HCl and (d) H2SO4. Set A Benzoic Acid, Isopropanol, Ethyl acetate, Acetophenone, n-hexane Set B Acetic anhydride, 2S-Butanol, Cyclohexene, Ethylamine, Acetanilide
A student was performing an acid-base extraction of a mixture of three compounds. The three compounds in the mixture are shown below. The mixture was extracted wilth 6 M HCI three times. The combined extractions were put into a flask marked A, which was treated with 1 M NAOH till it turned basic. This was then evaporated to obtain a crystal, which we label A. The remaining mixture was extracted with 6 M NaOH three times. The combined extractions were put into a flask marked A, which was treated with 1 M HCI till it turned acidic. This was then evaporaled to obtain a crystal, which we label B. The remaining mixture was evaporated to obtain a crystal, which we label C. The identity of A is Select] The identity of B is (Select) The identity of Cis Select] OH NH2 3
Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoicacid, phenol, benzyl alcohol, aniline
A mixture is made up of low molecular weight carboxylic acid, alcohol and ester. What one step procedure can you use to extract the ester component from the mixture? Describe the process briefly
0.2 gm of ethanol was acetylated with acetic anhydride in presence of pyridine (1:3), neutralization of the resulted solution required 20 ml of 0.1 N NaOH, while the blank titration reqiuered 40ml of NaOH. Calculate the percentage of hydroxyl group in this sample ?
6. Identify compound X in the scheme below. Ph LiAlH4 Et₂O then aqueous workup Dess-Martin or Ley or Swern or PDC compound X
A mixture of compounds is dissolved in ether, and extracted with 10% NaHCO3 solution. The aqueous extract is treated with 6M HCI solution, and extracted with dichloromethane. If the mixture contains an amine, where is it? The bottom layer of the first extraction O The top layer of the second extraction The top layer of the first extraction The bottom layer of the second extraction
2.1g of sample are dissolved in methylene chloride and the sample is extracted with an aqueous solution of acid and base. Three compounds are isolated - 0.7g of ethyl p-aminobenzoate, 0.6 g of acetanilide, and 0.5 g of benzoic acid. Calculate the % composition of ethyl p-aminobenzoate in the recovered mixture. (Round the answer to 1 significant figure. Give just the number, not a % sign.)
How do you construct a flow chart using extraction to separate a mixture of the 3 solids used below if dicholoromethane is the solvent and any other reagents can be used. The 3 solids are: pyrazole, p-chlorobenzoic acid, and benzophenone.
1. outline a procedure for separating a mixture of naphthalene (a neutral compound), toluic acid (an acidic compound), and p-bromoaniline (a basic compound). Assume that toluic acid and p-bromoaniline are completely insoluble in water. 2. The solubility of Lorazepam (a tranquilizer found in Emotival , Lorax, Wypax, and other prescription medicines) is 0.08mg/mL and 2.62mg/mL, in water and chloroform, respectively. Estimate the partition coefficient of lorazepam between chloroform and water. 3. The solubility of benzoic acid at 25 degrees Celsius in water and diethyl ether is 3.35 mg/mL and 0.353 g/mL, respectively. Estimate the percent recovery of benzoic acid in the organic phase, if a solution of benzoic acid in water is extracted with an equivalent volume of ether. [HINT-pay attention to the units] 4. The solubilities of cholesterol in water and chloroform are 0.550mg/100mL and 1.00g/5.25mL, respectively. Estimate the partition coefficient of cholesterol between chloroform and…