Carboxylic Acid Derivatives

These flashcards cover the key concepts related to carboxylic acid derivatives as discussed in the lecture, providing a basis for revision before the exam.

What are carboxylic acid derivatives?

Carboxylic acid derivatives are compounds that can be thought of as combinations of acids and other functional groups after losing water.

How are acid chlorides named?

Acid chlorides are named by changing the parent acid suffix from -ic acid to -yl chloride.

What characterizes acid chlorides in terms of reactivity?

Acid chlorides are very strong electrophiles and very reactive.

What is the naming convention for acid anhydrides?

Acid anhydrides are named by changing the parent acid suffix from acid to anhydride.

How are esters named?

Esters are named by changing the parent acid suffix from -ic acid to -ate, with the alkyl or aryl group bonded to the oxygen named first.

What is the naming rule for lactones?

Lactones, or cyclic esters, are named by changing -oic acid to -olactone.

What changes are made to the suffix when naming amides?

Amides are named by changing the parent acid suffix from -oic acid to -amide.

What is the classification of lactams?

Lactams are cyclic amides named by changing -ic acid to -lactam.

What are β-lactams?

β-lactams are antibiotics that contain a β-lactam ring in their chemical structure.

What are the general solubility characteristics of carboxylic acid derivatives?

The various carboxylic acid derivatives are generally less soluble in water than the parent carboxylic acids.

What is nucleophilic acyl substitution?

Nucleophilic acyl substitution is when a nucleophile adds into the carbonyl C=O of a carboxylic acid derivative, forming a tetrahedral carbonyl addition intermediate (TCAI).

What occurs during hydrolysis of acid chlorides?

Low molecular weight acid chlorides react rapidly with water to form new carboxylic acids.

What is the difference between acid and base hydrolysis of esters?

Acid hydrolysis of esters is a reversible reaction, while base hydrolysis (saponification) is irreversible.

What role do catalysts play in the hydrolysis of esters?

Catalytic amounts of H+ or equimolar amounts of −OH will promote the hydrolysis of esters.

What is saponification?

Saponification is the base hydrolysis of triglyceride esters, often used in soap making.