Carboxylic Acids and Derivatives Flashcards
What are the salts/anions of carboxylic acids?
carboxylates
How do you name carboxylic acids?
Replace the -e of the alkane with -oic acid
What are common names of carboxylic acids?
Acetic (ethanoic)
Formic (methanoic)
Carbonic (hydroxymethanoic)
Why do LMW carboxylic acids have high boiling points?
Polarity and the ability to H bond
What are the 4 features of carboxylic acid chemistry?
Hydrogen is weakly acidic
Carboxyl carbon is susceptible to nucleophilic attack
OH is a good leaving group in basic conditions
H bonding is possible both inter and intramolecularly
What does relative acid strength depend on?
the inductive effects of attached groups and their closeness to the carboxyl group
How can carboxylic acids be formed?
reacting a Grignard reagent with carbon dioxide or by reacting aldehyde with KMnO4.
What is the order of reactivity in carboxylic acids?
Acid chlorides > anhydrides»_space; esters > acids > amides > nitriles
If the nucleophile in a carboxylic reaction is -OR, what is the resulting compound?
An ester
If the nucleophile in a carboxylic reaction is NH₂, what is the resulting compound?
An amide
If the nucleophile in a carboxylic reaction is Cl, what is the resulting compound?
An acyl chloride
How do you reduce a carboxylic acid derivative?
LiAlH₄ or H₂/Metals
How do you name acid halides?
the ‘-ic acid’ of a carboxylic acid is replaced with ‘-yl halide’
e.g butanoyl bromide
How do you name acid anhydrides?
the ‘acid’ of carboxylic acid is replaced with ‘anhydride’
e.g ethanoic anhydride
How do you name amides?
replace the -ic acid of the parent anhydride with the suffix -amide.
If there are alkyl groups attached to the nitrogen, they are named as substituents with ’N’
e.g N-N-diethylacetamide
