10 Carboxylic Acids and Their Derivatives Free Online FlashCards

What are cyclic esters and cyclic amides called?

A cyclic ester is a lactone; a cyclic amide is a lactam.

How is an acyclic carboxylic acid named?

Choose the longest chain containing the carboxyl carbon, number that carbon as carbon 1, and use the ending -oic acid.

How is an ester named?

Name the group attached to oxygen first, then name the acid-derived part with the ending -oate.

How are amides named, including groups attached to nitrogen?

Replace -oic acid with -amide; identify groups attached to nitrogen with the prefix N-, as in N-methylpropanamide.

What are the key steps in nucleophilic acyl substitution?

A nucleophile attacks the carbonyl carbon to form a tetrahedral intermediate. The carbonyl then reforms as the leaving group departs; proton transfers may also occur.

Why do acyl derivatives undergo substitution rather than simple addition?

The tetrahedral intermediate can expel a group attached to the acyl carbon as the carbonyl reforms. Aldehydes and ketones lack this leaving group, so they undergo addition instead.

What two factors explain derivative reactivity differences?

Better leaving groups favor substitution, while strong resonance donation reduces carbonyl electrophilicity. Nitrogen donates strongly, making amides less reactive; carboxylates are especially unreactive because of their negative charge and resonance stabilization.

What does an alcohol form with an acid chloride?

An acid chloride reacts with an alcohol to form an ester by alcoholysis. A base is typically used to neutralize the HCl formed.

What are the conditions and equilibrium feature of Fischer esterification?

A carboxylic acid and an alcohol react with an acid catalyst, often with heat, to form an ester and water. The reaction is an equilibrium that can be shifted toward ester by using excess alcohol or removing water.

How is an acid chloride named from its corresponding carboxylic acid?

Replace -oic acid in the corresponding carboxylic acid name with -oyl chloride; for example, butanoic acid becomes butanoyl chloride.

How are acid anhydrides named?

Name the corresponding acid or acids, followed by anhydride. A symmetrical anhydride of ethanoic acid is ethanoic anhydride.

What products form when an ester undergoes basic hydrolysis, followed by acid workup?

Under basic hydrolysis conditions, an ester forms a carboxylate and an alcohol. Acid workup converts the carboxylate to a carboxylic acid.