Describe how to separate a mixture containing phenol, aniline, benzoic acid, and toluene.

Expert Solution

Phenol and benzoic acid are acidic, aniline is basic and toluene is an organic neutral compound. Add diethyl ether to the solution. Extract the ether solution with saturated NaHCO₃ solution in water.

The benzoic acid will be converted to sodium benzoate which will dissolve in NaHCO₃ solution. The aqueous layers are separated and acidify it with 5 N HCl converting the sodium benzoate back to benzoic acid.

Extract the remaining ether solution with 3N NaOH to convert the phenol to the sodium salt. Drain the lower aqueous layer and acidify it with 5 N HCl.

The ether layer contains both aniline and toluene. It is treated with 5N HCl; the aqueous layer containing anilinium salt is separated and treated with 3N NaOH to get free aniline.

The organic layer now contains only toluene; gently evaporate the ether (32 ^oC) leaving the toluene (110 ^oC).

queen_honey_blossom answered 10 months ago

Propose a method to separate a mixture containing phenol, benzoic acid, naphthalene, and p-nitro aniline. Phenol...

Propose a method to separate a mixture containing phenol, benzoic acid, naphthalene, and p-nitro aniline. Phenol is soluble in sodium hydroxide solution but insoluble in neutral water or sodium bicarbonate solution. Benzoic acid is soluble in either sodium hydroxide or sodium bicarbonate solutions. Write out the structures of the molecules in your scheme.

Describe how you would separate a mixture containing benzoic acid and a neutral substance, benzophenone. Both...

Describe how you would separate a mixture containing benzoic acid and a neutral substance, benzophenone. Both compounds are insoluble in water and soluble in ether.

2. Consider a sample that is a mixture composed of napthalene, benzoic acid, and phenol. The...

2. Consider a sample that is a mixture composed of napthalene, benzoic acid, and phenol. The sample is spotted on a TLC plate and developed in a hexanes/ethyl acetate solvent mixture. Predict the relative Rf values for the three compounds in the sample.

You are given 2.00 g of a mixture of phenol, aniline, phthalic acid and methyl benzoate....

You are given 2.00 g of a mixture of phenol, aniline, phthalic acid and methyl benzoate. Describe, how you would use an acid-base extraction technique to separate all three compounds by drawing the flowchart. Propose another way of extraction, where different order of extraction is used (e.g., adding the acid first instead of a base)

You need to separate a mixture of caffeine and benzoic acid. The sample has an initial...

You need to separate a mixture of caffeine and benzoic acid. The sample has an initial weight of 2.00 g and a content of 25.0% caffeine. You use dichloromethane, 10.0% NaOH solution, and 10.0% HCl. You are able to isolate 0.60 g caffeine and 1.00 g benzoic acid. Complete the following calculations and show your work. i)Calculate the amounts of caffeine and benzoic acid in the initial sample. ii) How much 10% NaOH solution would be needed to neutralize all...

benzoic acid naphthalene and aniline Which will be eluted first in reverse chromatography

Spectrophotometric Analysis of a Mixture: Caffeine and Benzoic Acid in a Soft Drink Benzoic Acid 230nm...

Spectrophotometric Analysis of a Mixture: Caffeine and Benzoic Acid in a Soft Drink Benzoic Acid 230nm 270nm 2mg/mL 0.231 0.034 4mg/mL 0.390 0.051 6mg/mL 0.539 0.058 8mg/mL 0.685 0.070 10mg/mL 0.888 0.094 Caffeine 230nm 270nm 4mg/mL 0.935 1.525 8mg/mL 0.285 0.442 12mg/mL 0.428 0.703 16mg/mL 0.624 1.066 20mg/mL 0.724 1.226 Soft Drink 230nm 270nm 2mL 0.738 0.273 4mL 1.313 0.522 Mountain Dew Caffeine:54mg/12fl oz Measure the ultraviolet absorption spectrum of the 2:100 and 4:100 dilutions of the soft drink. Find...

Suppose you want to separate a mixture of the following compounds: benzoic acid, m-cresol, p-aminobenzophenone, and...

Suppose you want to separate a mixture of the following compounds: benzoic acid, m-cresol, p-aminobenzophenone, and napthalene. Come up with a list of steps and chemicals needed to most efficiently isolate all four compounds as solids with the greatest purity possible.

5. Would it be easier or harder to separate cyclohexane toluene mixture or water methanol mixture?...

5. Would it be easier or harder to separate cyclohexane toluene mixture or water methanol mixture? Explain your answer.

Phenol is soluble in NaOH (aq) and not NaHCO3 (aq) while benzoic acid is soluble in...

Phenol is soluble in NaOH (aq) and not NaHCO3 (aq) while benzoic acid is soluble in both solutions. Explain how a mixture of phenol, benzoic acid, p-nitroaniline and anthracene can be separated by extraction. PLEASE Dont forget to talk about anthracene!

Question