CH 11: Reactions of Carboxylic Acids and Derivatives

IUPAC Rules for Naming Carboxylic Acids

1) Number the longest parent chain that ALWAYS assigns carboxylic acid as #1.

2) Name the parent chain, replacing -e with -oic acid.

3) Name the substituents along with their locants.

4) Check and name any stereochemistry for R/S, cis/trans, or E/Z.

5) List the stereochemistry first. Then, list substituents before parent name in alphabetical order.

List all of the functional group priority from highest to lowest.

carboxylic acid > esters > acyl halides > amides > nitriles > aldehydes > ketones > alcohol > amines > alkenes > alkynes > alkyl, ether and halides

What kind of BP (low or high) do carboxylic acids have? Why?

High BP b/c they are polar (dipole-dipole) and can H-bond

In what substances are carboxylic acid soluble in? insoluble in? any exceptions?

• soluble in 5% NaOH

• insoluble in water for containing 4 carbons or more

What reagents reacts with primary alcohol to form carboxylic acid?

Na₂Cr₂O₇ or CrO₃ or K₂Cr₂O₇, H₂SO₄, and H₂O

What reagents reacts with grignard reagent to form carboxylic acid?

CO₂ and H⁺

In acidic conditions, what reagents reacts with ester to form a carboxylic acid?

H⁺, H₂O or H₃O⁺, or H⁺, R-OH

In basic conditions, what reagents reacts with ester to form a carboxylic acid?

X⁺, ^-OH, H₂O or NaOH, H₂O