chapter 9: carboxylic acid derivatives

What effect does increased strain in a molecule have on its reactivity?

It makes the molecule more reactive.

Why are β-lactams prone to hydrolysis?

Because they have significant ring strain.

What causes ring strain?

Torsional strain from eclipsing interactions and Angle strain from compressing bond angles below 109.5°

What type of reactions can all carboxylic acid derivatives undergo?

Nucleophilic substitution reactions.

What can cleave anhydrides?

The addition of a nucleophile.

What is formed when ammonia or an amine is added to an anhydride?

Amide and Carboxylic acid

What is produced when an alcohol is added to an anhydride?

Ester and Carboxylic acid

What results from the addition of water to an anhydride?

Two carboxylic acids.

What is transesterification?

The exchange of one esterifying group for another on an ester.

What does transesterification require as an attacking nucleophile?

An alcohol.

Under what conditions can amides be hydrolyzed to form carboxylic acids?

Under strongly acidic or basic conditions.

What are the attacking nucleophiles in the hydrolysis of amides?

Water and Hydroxide anion

What influences the reactivity order in carboxylic acid derivatives?

Reactivity order: Anhydrides > Esters > Amides.

Which factors impact the reactions of carboxylic acid derivatives?

Steric hindrance and Induction

How does conjugation affect carboxylic acid derivatives?

It stabilizes and increases reactivity.

What two structures can form from the reaction of amines with carboxylic acid derivatives?

Amide and Carboxylic acid

What are amides derived from?

Condensation products of carboxylic acids and ammonia or amines.

What suffix is used for amides?

-amide

How are alkyl groups in substituted amides named?

Written at the beginning with the prefix N-.

What are cyclic amides called?

Lactams.

How are lactams named?

By the Greek letter of the carbon forming the bond with nitrogen.

What are esters the condensation products of?

Carboxylic acids and alcohols (Fischer esterification).

What suffix do esters use?

-oate

How is the esterifying group in esters named?

As a substituent, without a number.

What are cyclic esters called?

Lactones.

How are lactones named?

By the number of carbons in the ring and the Greek letter of the carbon forming the bond with oxygen.

What are triacylglycerols?

A form of fat storage with three ester bonds between glycerol and fatty acids.

What is saponification?

The breakdown of fat using a strong base to form soap.

What are anhydrides derived from?

Condensation dimers of carboxylic acids.

How are symmetric anhydrides named?

For the parent carboxylic acid followed by 'anhydride'.

How are asymmetric anhydrides named?

By listing parent carboxylic acids alphabetically followed by 'anhydride'.

How can some cyclic anhydrides be synthesized?

By heating dioic acids.

What ring sizes of cyclic anhydrides are generally stable?

Five- or six-membered rings.

What is the order of reactivity among amides, esters, and anhydrides?

Anhydrides > Esters > Amides.

What does steric hindrance refer to?

When a reaction is slowed due to crowding of substituents.

What can be used to increase steric hindrance?

Protecting groups, such as acetals.

What does induction describe?

Uneven charge distribution across a bond due to electronegativity differences.

How does electronegativity affect aromatic compounds?

More electronegative groups increase reactivity.

What is conjugation in chemistry?

The presence of alternating single and multiple bonds, creating delocalized electron clouds.

How does conjugation affect reactivity?

It stabilizes transition states, increasing reactivity.