chapter 8: carboxylic acids

What is the process called when mixing long-chain carboxylic acids with a strong base?

Saponification

What do soaps contain that gives them unique properties?

Hydrophilic carboxylate heads and Hydrophobic alkyl chain tails

What structural feature allows soaps to organize in hydrophilic environments?

They form micelles.

What is the role of a micelle in relation to nonpolar organic molecules?

It dissolves nonpolar organic molecules in its interior.

How can micelles be solvated?

They have an exterior shell of hydrophilic groups.

Identify a core property of carboxylic acids.

They are polar compounds known for their acidity.

What structural components compose carboxylic acids?

Carbonyl group and Hydroxyl group on the same carbon

What are two notable properties of carboxylic acids?

High boiling points and low pH

What type of reaction are carboxylic acids commonly involved in?

They undergo nucleophilic acyl substitution reactions.

Which component of soap is responsible for its ability to form micelles?

The hydrophilic heads.

What functional groups are present in carboxylic acids?

A carbonyl and a hydroxyl group on the same carbon.

What suffix indicates a carboxylic acid?

The suffix -oic acid.

How are salts of carboxylic acids named?

With the suffix -oate.

What suffix is used for dicarboxylic acids?

The suffix -dioic acids.

What is the polarity of carboxylic acids?

They are polar and form hydrogen bonds.

What effect does resonance have on the acidity of carboxylic acids?

Resonance enhances acidity through stabilization of the conjugate base.

What enhances the acidity of carboxylic acids?

Electron-withdrawing substituents enhance acidity; electron-donating decrease it.

What is special about the α-hydrogen in α-dicarboxylic acids?

The α-hydrogen is highly acidic.

How can carboxylic acids be formed from alcohols or aldehydes?

By oxidation using oxidizing agents like KMnO4 or dichromate salts.

What type of reaction is nucleophilic acyl substitution?

A nucleophile attacks the electrophilic carbonyl carbon, forming a tetrahedral intermediate.

What forms when a carboxylic acid reacts with ammonia or an amine?

An amide, named with the suffix -amide.

What do you call cyclic amides?

They are called lactams.

What forms when a carboxylic acid reacts with an alcohol?

An ester, named with the suffix -oate.

What forms when carboxylic acids react with each other?

An anhydride, with both linear and cyclic forms.

How can carboxylic acids be reduced?

To primary alcohols using LiAlH4 as a strong reducing agent.

Which reducing agent is commonly used but not strong enough for carboxylic acids?

Sodium borohydride (NaBH4).

What happens during the decarboxylation of β-keto acids when heated?

They lose a carbon as carbon dioxide via a cyclic intermediate.

What role do carboxylic acids play in the context of saponification?

They are key in the formation of soap.

What is the boiling point trend in carboxylic acids due to their properties?

They exhibit high boiling points due to hydrogen bonding.