Flashcards in Organic Chemistry Chapter 8: Carboxylic Acids Deck (17)
Suffix for salts
Suffix for dicarboxylic acids
high because of hydrogen binding
How is acidity enhanced?
resonance between its oxygen atoms
subsituents that are electron-donating
How can the acidity of c.a. be decreased?
substituents that are electron-donating
How can c.a. be made?
oxidation of primary alcohols or aldehydes using an oxidizing agent like potassium permanganate
What is a common reaction for carboxylic acids?
Nucleophilic acyl substitution
What happens in nucleophilic acyl substitution?
- Nucleophile attacks the electrophile carbonyl carbon
- Carbonyl reforms, kicking off leaving group
If nucleophile is ammonia or an amine?
Then an amide is formed
If the nucleophile is an alcohol?
Then an ester is formed.
If the nucleophile is another carboxylic acid?
an anhydride is formed
How can c.a. be reduced to a primary alcohol?
with a strong reducing agent, such as LiAlH4
Can NaBH4 reduce c.a.?
No - not strong enough
What happens to beta- carboxylic acids and beta-keto acids when heated?
they undergo spontaneous decarboxylation when heated, losing a carbon as carbon dioxide. This reaction proceeds via a six-membered cyclic intermediate.
What happens when you mix long-chain carboxylic acids with a strong base?
a salt we call soap - process = saponification