Ch 17 and Ch 19: Carboxylic Acids, Esters, Amides, and Amines

What two groups make up a carboxylic acid?

A carbonyl group (C=O) and a hydroxyl group (–OH)

What is the general formula for a carboxylic acid?

RCOOH or RCO₂H

What does the “R” represent in RCOOH?

The rest of the molecule, usually a carbon chain

What two groups make up an ester?

A carbonyl group (C=O) bonded to an –OR group

What is the general formula for an ester?

RCOOR′ or RCO₂R′

What two main groups make up an amide?

A carbonyl group (C=O) bonded to a nitrogen atom (N)

What can the nitrogen in an amide be bonded to?

Hydrogen atoms or carbon atoms

What makes an amide primary (1°)?

The nitrogen is bonded to 1 carbon and 2 hydrogens

What makes an amide secondary (2°)?

The nitrogen is bonded to 2 carbons, 1 hydrogen

What makes an amide tertiary (3°)?

The nitrogen is bonded to 3 carbons, 0 hydrogens

Amides are primary, secondary, or tertiary depending on the number of ______ atoms bonded directly to the nitrogen atom:

Carbon

What is the central structural feature of carboxylic acids, esters, and amides?

The acyl group (RCO)

What is the geometry of the acyl group?

Trigonal Planar

Is the acyl group polar or nonpolar?

Polar 

Which group in carboxylic acids allows them to form hydrogen bonds?

The hydroxyl group

Why do carboxylic acids have higher boiling and melting points than similar-sized esters and alcohols?.

Because hydrogen bonds between carboxylic acid molecules create stronger intermolecular forces

Out of carboxylic acids, esters, and alcohols, which has the highest boiling and melting point?

Carboxylic Acids

Which types of amides can form hydrogen bonds?

Primary (1°) and secondary (2°) amides

Why can’t tertiary (3°) amides form hydrogen bonds with each other?

Because they have no N-H group

Out of primary, secondary, and tertiary amides, which have the higher boiling and melting points?

Primary and secondary

Which molecule will have the higher boiling point?

B

__________ are more soluble in water than most other organic molecules:

Carboxylic Acids

Why can carboxylic acids dissolve better than most other organic molecules in water?

Because they can form hydrogen bonds with water molecules at their carbonyl and hydroxyl groups

How does hydrogen bonding affect the solubility of carboxylic acids?

It increases their solubility in water

Are short chain acids soluble or not soluble in water?

Soluble

Are long chain acids soluble or not soluble in water?

Not soluble

Are esters and amides soluble in water?

Yes

Why are esters and amides soluble in water?

Because they can form hydrogen bonds with water molecules

Which atoms in esters and amides allow hydrogen bonding with water?

The oxygen in esters and the nitrogen in amides

Compared to carboxylic acids, are esters and amides more or less soluble in water?

Less soluble

Are carboxylic acids strong or weak acids?

They are weak acids

Are carboxylic acids polar?

Yes

Are esters polar?

Yes

Are amides polar?

Yes

Which type of amide(s) cannot for hydrogen bonds with themselves?

Tertiary 

Can carboxylic acids form hydrogen bonds with themselves?

Yes

Can Esters form hydrogen bonds with themselves?

No

Can Amides form hydrogen bonds with themselves?

Yes but only primary and secondary

Which can form hydrogen bonds with water?

All- carboxylic acids, esters, and amides

Which are soluble in water?

All- carboxylic acids, esters, and amides

Which types of amides have stronger molecular forces and higher melting/boiling points?

Primary and secondary amides have stronger forces and higher BP than tertiary amides

______________ have very strong intermolecular forces and higher boiling/melting points than similar sized esters and amides":

Carboxylic acids 

What reaction type do acyl compounds undergo?

Substitution reactions

What is a substitution reaction?

When the group bonded to the carbonyl carbon gets replaced by another group (hydroxyl groups in carboxylic acids get replaced in this case)

What is esterification?

Substitution reaction of a carboxylic acid with an alcohol to form an ester and water

During esterification, carboxylic acids + _________ =  Ester and Water

Alcohol

During esterification, Carboxylic acids + Alcohol =  ________ and _______

Ester and water

What group is getting replaced during esterification and What group is replacing it?

The OH of a carboxylic acid gets replaced with OR of an ester

What is usually the catalyst during esterification?

H2SO4

What are amide formation reactions?

Substitution reaction of carboxylic acid with an amine to form an amide and water

During amide-formation reactions, carboxylic acid + _________ = Amide and water

Amine

During amide-formation reactions, carboxylic acid + amine = _______ and _______

Amide and water 

What group is getting replaced during an amide-formation reaction and what group is replacing it?

The OH of a carboxylic acid gets replaced with NR’2 of an amide

What is usually the catalyst during an amide-formation reaction?

Heat

Hydrolysis is taking a large molecule (ester or amide) and splitting it back into smaller pieces using _________:

Water (H2O)

Hydrolysis is basically undoing __________ and ___________:

Esterification reactions and amide-forming reactions

During hydrolysis, An ester + water = _______ and _______

Carboxylic acid and Alcohol

During hydrolysis, An amide + water = _______ and _______

Carboxylic Acid and ammonium

An amine is like an amide but doesn’t have a….

Carbonyl group

What is an amine?

A nitrogen atom bonded to a combination of hydrogen atoms and carbon groups

Amines and amides are alike because they both contain…

Nitrogen

To classify whether an amide is primary, secondary, or tertiary, you should count the…

The carbon + the number of R groups attached

To classify whether an amine is primary, secondary, or tertiary, you should count the…

Number of carbs attached to the nitrogen

A primary amine is a nitrogen atom bonded to _____ carbon atom(s):

1

A secondary amine is a nitrogen atom bonded to _____ carbon atom(s):

2

A tertiary amine is a nitrogen atom bonded to _____ carbon atom(s):

3

What are the reactants of esterification? (condensation)

Carboxylic acid and alcohol

What are the products of esterification? (condensation)

Ester and Water

What are the reactants of amide-formation reactions? (condensation)

Carboxylic Acid and Amine

What are the products of amide-formation reactions? (condensation)

Amide and Water

What are the reactants in the hydrolysis of esters?

Ester and Water

What are the products in the hydrolysis of esters?

Carboxylic Acid and Alcohol

What are the reactants in the hydrolysis of amides?

Amide and water

What are the products in the hydrolysis of amides?

Carboxylic Acid and Ammonium

Can amines form hydrogen bonds with each other?

Yes but only primary and secondary

Can tertiary amines form hydrogen bonds with themselves?

No (no N-H bond)

Amines have high boiling points, but they are less than ______:

Alcohols

Can amines form hydrogen bonds with water?

Yes

Are amines soluble?

Yes, but only ones with fewer than 6 carbons

Amines with ______ dissolve better in water:

H-bonds