Carboxylic Acid Derivatives Quiz

Carboxylic Acid Derivatives

• Carboxylic acid derivatives can convert into carboxylic acids or related derivatives.
• All derivatives have a carbonyl carbon located at carbon number 1.

Nomenclature of Carboxylic Acid Derivatives

• Carboxylic Acid: Suffix is -oic acid
• Acid Chloride: Suffix is -oyl chloride
• Acid Anhydride: Suffix is -oic anhydride
• Ester: Suffix is -oate
• Amide: Suffix is -amide
• Nitrile: Suffix is -nitrile

Carboxylic Acids

• Contain a carboxyl group (-COOH).
• Named with the suffix -oic acid, with the carbonyl carbon not included in the name.
• Example: Propanoic acid (common name: propionic acid).

Acid Chlorides

• Feature a carbonyl group bonded to a chlorine atom.
• Named with the suffix -oyl chloride.
• Example: Propanoyl chloride.

Acid Anhydrides

• Comprise two carboxyl groups bonded together.
• Named using the suffix -oic anhydride.
• In symmetrical anhydrides, the name simplifies to one carboxylic acid name.
• Example: Butenoic propanoic anhydride (asymmetrical), propanoic anhydride (symmetrical).

Esters

• Formed when a carboxyl group is bonded to an alkyl group.
• Suffix is -oate; base name derives from the carboxylic acid, not the alcohol.
• Example: Ethyl 3-methylbutanoate.

Amides

• Comprised of a carboxyl group bonded to an amino group.
• Suffix is -amide; nitrogen substituents indicated by a capital N.
• Example: N-methylpropanamide.

Nitriles

• Feature a carboxyl group bonded to a cyano group.
• Suffix is -nitrile; nitrile carbon included in the longest carbon chain.
• Example: Propanenitrile.

Physical Properties of Carboxylic Acids

• Display higher boiling points than anticipated due to dimerization and hydrogen bonding.
• Dimerization effectively doubles molecular size, enhancing van der Waals forces and boiling point.

Overview of Carboxylic Acid Derivatives

• Carboxylic acid derivatives can convert into carboxylic acids or other derivatives.
• All derivatives feature a carbonyl carbon at carbon number 1.

Nomenclature of Carboxylic Acid Derivatives

• Carboxylic Acid: Suffix -oic acid
• Acid Chloride: Suffix -oyl chloride
• Acid Anhydride: Suffix -oic anhydride
• Ester: Suffix -oate
• Amide: Suffix -amide
• Nitrile: Suffix -nitrile

Carboxylic Acids

• Comprised of a carboxyl group (-COOH).
• Named with the suffix -oic acid and the carbonyl carbon is not numbered in the name.
• Example: Propanoic acid (also known as propionic acid).

Acid Chlorides

• Contains a carbonyl group bonded to a chlorine atom.
• Denoted by the suffix -oyl chloride.
• Example: Propanoyl chloride.

Acid Anhydrides

• Comprise two carboxyl groups bonded together.
• Named with the suffix -oic anhydride.
• For symmetrical anhydrides, the name includes only one carboxylic acid name.
• Examples: Asymmetrical - butenoic propanoic anhydride; Symmetrical - propanoic anhydride.

Esters

• Feature a carboxyl group linked to an alkyl group.
• Named with the suffix -oate, based on the carboxylic acid rather than the alcohol.
• Example: Ethyl 3-methylbutanoate.

Amides

• Contain a carboxyl group bonded to an amino group.
• Indicated by the suffix -amide.
• If nitrogen has substituents, they are represented with a capital N.
• Example: N-methylpropanamide.

Nitriles

• Contain a carboxyl group bonded to a cyano group.
• Suffix used is -nitrile.
• The carbon of the nitrile is counted in the longest carbon chain.
• Example: Propanenitrile.

Physical Properties of Carboxylic Acids

• Higher boiling points than expected due to dimerization and intermolecular hydrogen bonding.
• Dimerization increases molecular size, enhancing van der Waals forces and raising boiling points.