carboxylic acids Flashcards
What are the properties or carboxylic acids?
C and O are sp2 hybridized. Has resonance. More stable than alkene. Higher BP and MP
What property of carboxylic acids results in a higher boiling and melting point?
Hydrogen bonding. Also results in increased water solubility
How does inductive polarity affect carboxylic acid acidity?
C=O is EWG and has resonance for stabilization
How does a negative charged O affect stabilization?
No resonance so no stabilization
How is stability related to formation?
More stable = more easily formed = more willing to give up H
Reaction conditions to form carboxylic salts?
Reactants: carboxylic acid
Conditions: NaOH or KOH
Product: carboxylic salt C=O and O-
How do you form a dicarboxylic acid?
Reactant: dicarboxylic acid
Conditions: 2 eq of NaOH
Product: dicarboxylic salt
What are five ways to form carboxylic acids?
- 1ºROH with K2Cr2O7|H2SO4, H2O
- Aldehyde with K2Cr2O7|H2SO4, H2O
- Phenyl with K2Cr2O7|H2SO4, H2O
- Gringard with 1. CO2, ether 2. H3O+ (extends by one C)
- Nitrile (R-C=N) with H2O, H2SO4| heat or 1) KOH, H2O, heat 2) H3O+ (extends by one C)
What are the reaction conditions for the preparation of nitriles?
Reactants: alkyl halide
Conditions: NaCN or KCN
Product: R-CN
R= methyl, primary or secondary
Reaction conditions of carboxylic acid to acyl chloride?
SOCl2
Reaction conditions to go from carboxylic acid to alcohol?
1) LAH, ether 2) H2O
Reaction conditions for Fischer esterification?
Reactant: carboxylic acid
Conditions: alcohol, acid catalyst
Product: ester + water
Reaction conditions of secondary esterification reaction?
Reactant: carboxylic acid
Conditions: NaH then alkyl halide
Product: ester
*forms carboxylic salt intermediate
Reaction conditions for decarboxylation?
Reactant: any molecule with beta C=O (anhydride)
Conditions: heat
Product: CO2+ carboxylic acid, ketone, aldehyde (depends on anhydride group)
What occurs in intramolecular esterification?
Carboxylic acid with alcohol on the end forms lactones
