Because phenol (C6H5OH) is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCO3. Using this information, write out an extraction sequence that can be used to separate C6H5OH, benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.

Because phenol (C6H5OH) is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCO3. Using this information, write out an extraction sequence that can be used to separate C6H5OH, benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.

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

Chapter19: Enolate Anions And Enamines

Section19.3: Claisen And Dieckmann Condensations

Problem 19.6P

See similar textbooks

Similar questions

Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoicacid, phenol, benzyl alcohol, aniline
Explain this statement: Although 2-methoxyacetic acid (CH3OCH2COOH) is a stronger acid than acetic acid (CH3COOH), p-methoxybenzoic acid (CH3OC6H4COOH) is a weaker acid than benzoic acid (C6H5COOH).
Explain this statement: Although 2-methoxyacetic acid (CH3OCH2COOH)is a stronger acid than acetic acid (CH3COOH), p-methoxybenzoic acid(CH3OC6H4COOH) is a weaker acid than benzoic acid (C6H5COOH).
Tell whether each of the following experimental errorss will raise or lower the amount of each product recovered: (the benzoic acid, 4-chloroanaline, and naphthalene); why-You do not remove all of the HCl from the first extraction -You forget to do the NaOH extraction -You do not rotovap all of the solvent in the final step
In Part 1, draw the mechanism for the most likely proton transfer reaction between methanol and 2-methylpropanoic acid. In Part 2, indicate which side of the reaction is favored at equilibrium.
Show how to convert the side-chain carboxyl group to a benzyl ester using benzyl chloride as a source of the benzyl group.
Carboxylic acids are acidic enough to dissolve in both 10% NaOH and NaHCO3. Phenols, ArOH, are weak acids and most phenols will not dissolve in 10% NaHCO3. How would you separate a mixture of a carboxylic acid (RCOOH), an amine (RNH2), a phenol (ArOH) and a hydrocarbon (RH) using chemically active extraction? Draw a flow chart to illustrate your separation. Show each species in the aqueous and organic layers.
3. If you have an unknown carboxylic acid, what pH you need to achieve upon re-acidification with HCl to ensure that your carboxylic acid is 99.9% back in its charge neutral form?Assume a pKa of 5 for your carboxylic acid, and remember that the pH needs to be 3 units different from the pKa for 99.9% ionization or charge neutralization. pH 7 or lower pH 5 or lower pH 2 or lower pH 13 or lower
What is the oxidation product of methanol inside the body and why is it harmful? Write your observation based on the acidic properties of each sample Sample Observation 1-butanol 2-butanol 2-methyl-propanol
The order of addition of the bases is important. What would have happened if you instead treated the initial mixture of benzoic acid, 2 - napthol and 1,4-dimethoxybenzene with a 1M NaOH aqueous solution instead of the saturated NaHCO3 solution? How would the separation of the compounds be affected? What would change?
3. You are given a mixture of aspirin, phenol, and naphthalene that you need to separate. i) Draw the structures of each, and identify if they are acidic, basic, or neutral compounds. For each compound draw their reaction with the appropriate acidic or basic conditions that will change their solubility and allow them to be separated. ii) What modifications would you have to make to the experimental protocol in order to separate these three compounds? Provide specifics.
Give 2 different one-step methods to convert propanoic acid to methyl propanoate.