Organic Chemistry Chapter 8: Carboxylic Acids

Question 1

Suffix

Answer 1

-oic acid

Question 2

Suffix for salts

Answer 2

-oate

Question 3

Suffix for dicarboxylic acids

Answer 3

-dioic acids

Question 4

Boiling points

Answer 4

high because of hydrogen binding

Question 5

How is acidity enhanced?

Answer 5

resonance between its oxygen atoms

subsituents that are electron-donating

Question 6

How can the acidity of c.a. be decreased?

Answer 6

substituents that are electron-donating

Question 7

How can c.a. be made?

Answer 7

oxidation of primary alcohols or aldehydes using an oxidizing agent like potassium permanganate

Question 8

What is a common reaction for carboxylic acids?

Answer 8

Nucleophilic acyl substitution

Question 9

What happens in nucleophilic acyl substitution?

Answer 9

• Nucleophile attacks the electrophile carbonyl carbon

- Carbonyl reforms, kicking off leaving group

Question 10

If nucleophile is ammonia or an amine?

Answer 10

Then an amide is formed

Question 11

If the nucleophile is an alcohol?

Answer 11

Then an ester is formed.

Question 12

If the nucleophile is another carboxylic acid?

Answer 12

an anhydride is formed

Question 13

How can c.a. be reduced to a primary alcohol?

Answer 13

with a strong reducing agent, such as LiAlH4

Question 14

Can NaBH4 reduce c.a.?

Answer 14

No - not strong enough

Question 15

What happens to beta- carboxylic acids and beta-keto acids when heated?

Answer 15

they undergo spontaneous decarboxylation when heated, losing a carbon as carbon dioxide. This reaction proceeds via a six-membered cyclic intermediate.

Question 16

What happens when you mix long-chain carboxylic acids with a strong base?

Answer 16

a salt we call soap - process = saponification

Question 17

Micelle

Answer 17

dissolves nonpolar organic molecules in its interior, and can be solvated with water due to its exterior shell of hydrophilic groups.