Lectured

January 1312023 Acidic Proton

of

Rican É

pilot tht

at
p carboxylate

avion

more stable
R E

than other anions prison and

such R
Stabilization

as
E

Alkoxides

acid are more acidic

Therefore

fan alcohols or water

I1

structure of R.com s

affects carboxylate R OH 16 18

and H on

stability pkg 15.7

Preparation of carboxylic

acids

7 Oxidation

alcohols and aldehydes

Ong reagents

with

Ktla 04 Cro Maso

Hero

HNos

Jones Cros
oxidation
this

Tom

Troy
Hedy

terra
P

add a new

fezson H2O

Cro t Mason D Heron t so

Discussed in detail in

Chapter 8.51 Alcohols

17.4 Carbonyl compounds

Addition of Grignard reagents

to Coz ÉgBr

cHzcrMrtÉ

t a

crease to

carboxylate

quench
Adds

new
M

ago Carbon

o 6

propionic acid

nitriles

Hydrolysis of

ÉWÉÉNR cen R Con

Br I
D to or 204kg halide

mechanism to be
discussed in a

later lecture
Problem carbon

I É gittra
8893559
Hsr
Fae
I coz Grignon
adair
rightist
EEF yet
Halide

Reactions of Carboxylic

O _É
RIE o It R Ko H

Nuit 5.0
Nucleophile base
 Protonation of farboxylie Acids

my
g want
6 to 7
plat Stabilized
resonance
by

Nucleophilic Addition Elimination

Addition Elimination

Finger.us
nÉ Er In
TETRAHEDRAL
Carboxylic
4 Acid
INTERMEDIATE derivative
Good nucleophile substitution
Formally a

Non basic substitution

 Compare to Nucleophilic Addition

toyboy groupie
eat

atty NÉ crestNue

if NÉ is Basic Ania
Had Base reaction

2 Ht NacCB RÉ t H NuelBl

T T
no
longer no
longer
electrophile nucleophile
I
 I
Nucleophilic Addition Elimination

pill the Rinne t

substitution
formally a
but different from Sn or Sara

Carboxylic XadsAad base no longer

e Kat to it
tinny
T T not
electrophilic
Acidic
Proton
yup can ago

basi Nuc hittites

Strange

basichucleophiles
weakly Rio.tl catalyst