Carboxylic Acid Derivatives Flashcards
(23 cards)
What is the general formula of esters?
Carbonyl group bonded to OR
How are esters named?
The group bonded to the single bonded oxygen is named as a alkyl/aryl group and the group containing the carbonyl group is named as alkyloate
What is a cyclic ester called?
A lactone
What are the common uses of esters?
Flavoring and scent, medications like aspirin (ASA)
How are esters hydrolyzed in acid?
Reverse of esterification. When heated in hot aqueous base, excess of water drives the reaction to produce alcohol and carboxylic acid
How are esters hydrolyzed in base?
Saponification. Base is a reactant. Hydroxide ion reacts with carboxylic acid to form carboxylic acid anion
What is the general structure of an anhydride?
An oxygen atom between two carbonyl groups with R groups on each side
How are anhydrides named?
The groups containing the carbonyl groups on either side are listed alphabetically before the word anhydride
What is the general structure of an amide?
A nitrogen atom bonded to a carbonyl group
How are amides named?
Carboxylic acid suffix is replaced with “amide.” The prefix “N-“ is used to represent multiple groups bonded to the nitrogen.
What is a cyclic amide called?
A lactam
How are amides synthesized with ammonia?
Carboxylic acid + ammonia = primary amide + water. Heat is required
How are amides synthesized with an amine?
Carboxylic acid + amine = ammonium salt which is converted to an amide and water with heat
How are amides synthesized with an anhydride?
Anhydride + amine = amide + carboxylic acid
How are anhydrides hydrolyzed?
Anhydride + water = RCOOH + HOOCR
How are amides hydrolyzed in aqueous acid?
Amide + Water + Acid = Carboxylic acid + ammonoium salt. Heat is required
What is the stoichiometry of the hydrolysis of amides in acid?
Each mole of amide hydrolyzed needs one mole of acid
How are amides hydrolyzed in aqueous base?
Amide + Base = carboxylic acid salt + ammonia or amine
What is the stoichiometry of the hydrolysis of amides in base?
Each mole of amide hydrolyzed needs one mole of base
How do anhydrides react with alcohols?
Alcohol + anhydride = ester + carboxylic acid. Alcohol reactant should be similar to ester product and anhydride reactant should be similar to acid product
How do anhydrides react with amines?
Anhydride + ammonia/1° amine/2° amine = amide
What is the stoichiometry of the reaction of anhydrides and amines?
2 moles of amine or ammonia required per mole of anhydride
How do esters react with amines?
Ester + ammonia/1° amine/2° amine = amide
