▷ Carboxylic acids and Derivatives – Organic Chemistry – list of solved problems

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Carboxylic acids and derivatives – problem list

Problem 1)

Rank in increasing order of acidity the following series of carboxylic acids.

a) HCOOH, CH₃-CH₂-COOH, CH₃-COOH
b) CH₃-COOH, CCl₃-COOH, CHCl₂-COOH, CH₂Cl-COOH
c) CH₃-COOH, CH₂F-COOH, CH₂Br-COOH, CH₂Cl-COOH
d) CH₃-CH₂-COOH, CH₂Cl-CH₂-COOH, CH₃-CHCl-COOH

Problem 2)

Represent the resonant structures of the conjugate base of acetic acid.

Problem 3)

Indicate the product obtained by treating acetic acid with the following reagents:

a) Ammonia
b) Thionyl chloride
d) Hot aniline
e) Phosphorus pentoxide
f) Isopropanol in acid medium

Problem 4)

Describe in detail the mechanism of ester formation in acid medium, and indicate some procedure to promote the shift of equilibrium towards ester formation.

Problem 5)

Indicate the result of treating propyl pentanoate with an excess of methanol in acid medium.

Problem 6)

Describe the result of treating benzoyl chloride with 4-aminobutan-1-ol.

Problem 7)

Represent the scheme of the reaction that takes place when acetic anhydride is treated with p-chloroaniline.

Problem 8)

Assuming you have three bottles of chlorobenzene, chlorobutane, and benzoyl chloride whose labels have been misplaced, how would you know which one is which by some simple analytical test?

Problem 9)

Indicate what is the result of reacting salicylic acid (2-hydroxybenzoic acid) with acetic anhydride.

Problem 10)

What is the result of reacting succinic anhydride with ethylamine?

Problem 11)

Propose a method for the synthesis of N-methylbutanamide from an ester.

Problem 12)

Draw the structure of the compounds obtained in the acid, HCl, (dilute) and basic, NaOH, (dilute) hydrolysis of a) ethyl acetate, MeCOOEt and b) methyl propanoate, EtCOOMe.