COOH Flashcards
What increases COOH acidity?
Stability of the c. Base:
C base has resonance
Or
(In the case of a ring) c. Base has e- withdrawing substituents that stabilize the ring by drawing e- density AWAY from the ring
On nomenclature: how can you tell from a structure (like C6H5CO2H) that there must be a ring in there somewhere?
You’ll have way too few hydrogens to satisfy the carbons in a linear structure
On what COOH position can a substituent cause the biggest increase acidity?
The alpha position (the R from the COOH)
What are the 5 ways you can make a COOH?
- Oxidative cleavage of alkYNES
- Oxidation of primary alcohols
- Oxidation of alkylbenzenes
- Hydrolysis of nitriles
- Grignard reagent
In a nucleophilic acyl substitution rxn, which 3 situations require you to do a proton transfer?
- Rxn beginning: poor starting materials
- Rxn middle: charged tetrehedral intermediate and/or neutral leaving group
- Rxn end: charged product
How does an alcohol’s acidity compare with a COOH’s?
COOH is way more acidic than alcohol (bc COOH electron withdrawing groups and resonance from the carbonyl makes its conjugate much more stable than alcohol’s conjugate)
Why do you mix up the grignard and the LAH rxns with ester COOH derivatives?
They look alike and have the same denominator, but they are not alike
What’s the difference in reactants between grignard and the LAH rxns with ester COOH derivatives?
grignard has xs RMgBr and H2O but LAH reduction has xs LAH and H2O
what is pyridine for?
,
when a grignard attacks an acid chloride to replace it’s substituents with 2 R groups, when does the oxygen get protonated?
At the VERY end/last step- p 1009 in book
when you break the ring of an ester to do rxns, where do you break it?
Between the two Os
when you break the ring of an ester to do rxns, WHEN do you break it?
during the LG step
what is the pattern when you react ester (in a ring) with LAH, H2O?
nuleate, protonate, nucleate, protonate
