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
what is produced when acyl chlorides react with +H2O
COOH
what is produced when acyl chlorides react with +ROH
ester
what is produced when acyl chlorides react with RCO2H
anhydride
what is produced when acyl chlorides react with 1. RMgX and 2. H3O+
tertiary alcohol
to produce a amide from an acid anhydrideswhat reactants and reagents are required
+R-NH2
to produce a COOH from an acid anhydrideswhat reactants and reagents are required
+H2O
to produce a ester from an anhydride what reactants and reagents are required
+ROH
what is produced when acid anhydrides react with +R-NH2
amide
what is produced when acid anhydrides react with +H2O
COOH
what is produced when acid anhydrides react with +ROH
ester
can acid anhydrides form acyl chlorides why
no cant convert directly to acyl chloride as its less reactive than acyl chlorides
how do you prepare esters - 2 ways
acid anhydrides/halides + alcohol
or
COOH + alcohol via H+
what are the 2 reactions esters undergo
nucleophillic acyl substitution
hydrolysis
to produce an amide from an ester what reactants and reagents are required
+RNH2
to produce an primary alcohol from an ester what reactants and reagents are required
- LiAlH4
- H3O+
to produce an tertiary alcohol from an ester what reactants and reagents are required
- 2RMgX
- H3O+
what is produced when esters react with +RNH2
amides
what is produced when esters react with
- LiAlH4
- H3O+
primary alcohol
what is produced when esters react with
- 2RMgX
- H3O+
tertiary alcohol
to produce an COOH and R-OR group from an ester what reactants and reagents are required
H2O/H3O+
or
H2O/OH-
(base will cause carboxylate ion or COO-)
how are amides prepared
acid halide/anhydride + amine
how are primary amides produced, what reagents and reactants are needed
+NH3
ammonia
how are secondary amides produced, what reagents and reactants are needed
+ R-NH2
primary amine
how are tertiary amides produced, what reagents and reactants are needed
+ R2-NH
secondary amine
what are amides
RCO-NR2
what are the 3 reactions amides can undergo
hydrolysis
nucleophillic acyl substitution
polyamide formation
for an amide to undergo hydrolysis what reactants or reagents are required
70% aq H2SO4/heat
for an amide to undergo nucleophillic acyl substitution to form amines and water what reactants or reagents are required
+OH-
for an amide to undergo polyamide formation what reactants or reagents are required
diacid chloride + diamine
via HCl
what is produced when amides undergo hydrolysis via 70% H2SO4 aqueous/heat
R-NH3+ + RCOO-
what is produced when amides undergo nucleophillic acyl substitution with OH-
RNH2 + H2O
what is produced when amides undergo polyamide formation via HCl
forms amide bond
(-CO-NH-)
