8. Carboxylic Acids & Derivatives Flashcards
what has the greatest and least acidity of the following
phenol, alcohols, COOH
COOH > phenols > alchols
what does e- donating substituents do to the acidity or acid strength and pka
decrease acid strength
increase pka
what does e- accepting substituents do to the acidity or acid strength and pka
increase acid strength
decrease pka
what are the 3 ways COOH is prepared
oxidation of alcohol
Grignard addition to CO2
nucleophilic substitution of alkyl halide
what reagents or reactants are needed to prepare COOH from alcohol oxidation
primary alcohol
H2CrO4
what reagents or reactants are needed to prepare COOH from Grignard addition to CO2
- RMgX + CO2
- H3O+
what reagents or reactants are needed to prepare COOH from nucleophilic substitution of alkyl halide
- CN-
- H3O+
add CN- to halide RX and then react with acid to get COOH
what does COOH react with metals to produce
salt and H2 gas
what does COOH react with metal carbonates to produce
salt, water and CO2
what are the 3 types of acid derivatives
acyl chlorides and anhydrides
esters
amides
how are acyl chlorides prepared, what reagents and reactants are required
COOH + SOCl2
how are symmetrical anhydrides prepared, what reagents and reactants are required
RCOOH + P2O5
what is produced when COOH + P2O5
symmetrical anhydrides
how are unsymmetrical anhydrides prepared, what reagents and reactants are required
RCOOH + RClC=O = both symmetrical and unsymmetrical anhydrides
what is produced when RCOOH + RClC=O
both symmetrical and unsymmetrical anhydrides
to produce an amide from an acyl chloride what reactants and reagents are required
+H2NR
to produce an COOH from an acyl chloride what reactants and reagents are required
+H2O
to produce an ester from an acyl chloride what reactants and reagents are required
+ROH
to produce an anhydride from an acyl chloride what reactants and reagents are required
+RCO2H
to produce an tertiary alcohol from an acyl chloride what reactants and reagents are required
1.RMgX
2. H3O+
what is produced when acyl chlorides react with +HN-R
amide