Why are carboxylic acids so much more acidic than their alcohol analogs?
Answer:
1. The carbonyl group is electron-withdrawing. It stabilizes the acetate anion, contributing to the carboxylic acid's acidity.
2. The carbonyl group also allows for electron delocalization, with resonance between the two oxygens, again stabilizing the acetate anion
Learn More :
Carboxylic Acids
- What are the reagents needed for Lithium Aluminum Hydride reduction of carboxylic acids? What is the overall result?
- Name 3 reactions of carboxylic acids presented in the chapter:
- Name three reactions given by the chapter which you can use to synthesize carboxylic acids without adding a carbon to the parent chain:
- How do you decarboxylate malonic acid?
- How are lactones named?
- What are "lactones"?
- What is the skeleton reaction of acid-catalyzed esterification?
- What are the products when carboxylic acid is reacted with 1. LiAlH4, diethyl ether 2, H2O?
- What is(are) the products when carboxylic acid is reacted with thionyl chloride?
- When acid-catalyzed esterification is carried out, where does the hydroxyl oxygen come from?
- Given an alkyl chloride, how would you carboxylate it and add to the chain by one? (cyanide method)
- Given an alkyl chloride, what are the three reagents (in order) needed to carboxylate the compound while adding another carbon to the chain? (carbon dioxide method)
- Name two ways to prepare carboxylic acids while extending the parent chain by a carbon:
- How do you oxidize aldehydes?
- How do you oxidize a primary alcohol?
- How do you convert a primary or secondary alkyl side chain on an aromatic ring to a carboxyl group?
- What is the reaction most used for the commercial production of acetic acid?
- How does bicarbonate compare in acidity to carboxylic acids, water, and alcohol?
- What happens when an amphiphilic substance is placed in water?
- What is the definition of an amphiphilic substance?
- Which parts of sodium stearate are hydrophilic, and which parts are lipophilic?
- How do you name the carboxylic acid salts?
- What happens to carboxylic acids in the presence of strong bases such as NaOH?
- In substituted benzoic acids, the largest effects on acidity occur when the electron-withdrawing substituents are in which location?
- Does carbon become more or less electron-withdrawing as its s-character increases?