Carboxylic Acids Flashcards
Lactic Acid name
2-hydroxypropanoic acid
Simplest carboxylic acid
Formic acid
Derivatives of carboxylic acids
Acid halide
Ester
Acid anhydride
Acid amide
Nitrile
Common names of carboxylic acids
1 = Formic acid (ant)
2 = Acetic acid (vinegar)
3 = Propionic acid (first/fat)
4 = Butyric acid (butter)
5 = Valeric acid (valerian plant)
6 = Caproic acid
Common names of:
Ethanedioicacid
Propanedioicacid
Butanedioicacid
Oxalic acid
Malonic acid
Succinic acid
Acid halide IUPAC names
-oyl chloride
Esters IUPAC naming
alcohol alkyl -yl then carboxylic acid alkyl -oate
-yl -oate
Acid anhydride IUPAC naming
-oic anhydride
Functional group isomers?
Carboxylic acids and esters
Tautomerism
Resonance (switching the bond from one to another)
Carboxyl group bond angle
120º
C1-C3 of carboxylic acids are
Colorless liquids/pungent smell
C1-C9 are
liquids
C10 + are
solids with little odor
Carboxylic acids are _______ polar than alcohols
more
NO2 is electron
Withdrawing
Halogens are electron
Withdrawing
Electron withdrawing substituents _________ the strength of acidity
Enhance/Increase/Support
Carbonation of Grignard Reagant
Grignard Reagant + CO2 (in dry ether) —> Addition product
Addition product + (H3O+) —> Carboxylic acid (one more C than Grignard Reagant)
Preparations of Carboxylic acids
Carboxylation of Grignard Reagant
Hydrolysis of Nitriles
Oxidation of Primary Alcohols
Oxidation of Aldehydes
Oxidation of Alkyl Benzenes
Intermediate of “Hydrolysis of Nitrile” Reaction
Amide intermediate
Oxidation of Primary Alcohols gives what intermediate
Aldehyde intermediate
In oxidation of alkyl benzenes what happens
Alkyl groups attached to the benzene ring turn into carboxylic acid groups (if more than one alkyl group then one becomes -COOH and the rest become CO2)
Color change in oxidation of alkyl benzenes
From purple (KMnO4) to dark brown ppt (MnO2)
What type of reactions do carboxylic acids mostly go thru
Nucleophilic acyl substitution reactions
Most reactive carboxylic acid derivative
Acyl halide / Acid halides
How to get acid halides from carboxylic acids
SOCl2 or PCl5 or PCl3
Carboxylic acids to acid anhydrides needs
Dehydrating agent (P2O5)
Esters can also be made by adding alcohol and ____
Acid halide or acid anhydride
For acid halide pyridine is used to consume the HCl
Least reactive derivative
Amides
Carboxylic acids to amides needs
Ammonia to form ammonium salts which on heating produce acid amides
Amides can also be prepared by the reaction of ammonia with
Acid chlorides, esters, acid anhydrides
Reduction of carboxylic acids to alcohols needs
LiAlH4 + dry ether
Decarboxylation reactions need
NaOH + (CaO and heat)
Product gives alkane with one less C than parent carboxylic acid
Malic acid found in
Apples
Tartaric acid found in
Grapes
Oxalic acid found in
Vegetables
Benzoic acid and sodium benzoate have
Have inhibitory effects on growth of fungi
Alkoxy carbonyl functional group is present in
Ester
