CARBOXYLIC ACID

Structure & Properties.

RCOOH
0 13-5 o
Il H
-
xo RC02H
acid
Carboxylic

Reactivity:
Addition -

Elimination (Nucleophilic Acyl Substitution)

:: Elimination O
I
0 Additional.
D I
Not ->
q Sitei Nr
ILG
me No I

LG:

Aldehyde
ixion join
Ketone
o R andH
NO

FLG

Relative Reactivity
0

y
Et 4
C 0 =
↑ Reactivity
 Most Reactive
ing Reactivity
-
>
Least
reactive.
0

+xx R i
00

Mort MoH
-

Halide Carboxylic acid

c0
= Acyl Anhydride star.
I

Amide.
1800
~
1800 1720
IR
~
-
~
1710 ~
1650
1750
cam-i
~

NMR: y
63 -

at
62

the
4

e
-

8408

Ye
↓
6300
o

-100
810-12
220
↓Il H

o*xchangeable X

q
8 170-180
#H
-
82.5 3
-
1170 +80 tothe
8 2.5-3

=e

PREPARATION:4 methods

Method 1:TONES or NacCrO7, HaSO4 orKeCMaO7

on
H1H
Not
JONES

NamaG7, HaS0p(ag)
or kaC07

ethods #2: kMnOp (ag)

coaq)x
O
1c =

/ - t
↑
H -25°
Methods 3:RC=N
Hydrolysis m/HY, Hc0

R -

N
= H
HaO, II
C
-

H2SO4(ag) /4 0H
R

-H
·hi
i
-
echanism:

on
A
-HSOH -cm*-488sH
/
-cEN:
h
Ha:

H
-
ii H

*T
-

!= He M
#
=-
- 4): d
+

R 0:
=

R
Ha.
NH 3
+

d &*NH, H
⑦
0
"
d ↳I:
11
--
/
2 -
↓
OH , C NH
·
- " -
*NH4
+

R
-

-
I o
0H I ON
La R
H OH
H

Method #4:CO2

⑧
Il
R-MgX CO2 C
or - R
--
OH
R-Li

Assumed
↳
Mechanism: 0
I HY, H20w/o 0
- s * II

p 20
0 c 0
=

R-4*
= -

R-a- 0H
-
a

MgX
(Lie)
REACTION (Just [H]
for Non]

&COOH [H]: LAH4

From
Not

on Hy Hy
i*HY
Na e

Mechanism:
H
Hi

+H4F **
I

oft H- AIEH
I
->
-
-
H

H
H
AT,"
: H

Da
A.
pro-A*orcist
Addition
-> - immation ce
No In
H

Addition N- 08a HT, H20 work up

H H

:- V
- >

- -
(Assumed - OH
*i
H

perivatives:
1) Halide. O
Il X:CI is most common
*

-ar PREP:I method

~

OH I

on a
N
as

⑰ :I ⑩
O
Il

r FOR

-Mg,
hte, e
(xs O

alsothe
0
-
I
-
Deliver s

"R"
⑧
J.I
Ra
cuLl Acyl Halide
-

o -or Ho
aiN ·sor
only one
Il ↳ cupmateagen Lox
-
R
i9

⑨ H
 , joee
O

a.
(a Elim Il
/Nr +: ①

Well
strong

lyHyg. to de A

gte MoH
Elimination
->
-
+:ci8 -> +
Ha(g)

a ,
4 Exete ③

omgaxconation,edition,
⑭
↳
My R-Mgx dition
R
Ketone.
R -MgX

joimination
H

-
P
&H
Cl
Addition
->

Li
jot AH
I

A8 -Al2
H -

-
ITH
H
yup,
⑥ :-A(OR3) ⑧
ICOR), A(OR)s
i
: -
-

("
⑦

-Ni
tion,
*

II
⑦
Cl
Li I H
+
, H20
RO Al OR
↳ w/u ⑧

is
Here
varyorone." I
i
acanoes ⑧

Il

RI
or po
Anhydrids
R, Ra
=
or R, F Re
↓ ↓

Symmetrical Unsymmetrical.

⑧
II
Preparation:2 methods: R
-
iP
or

① O

I
a For, Yo
Symmetrical on
Unsymmetrical.

⑳ 0
⑧ ⑧
Diluted
↓

R
2
off.
1s
How
II
Ha8
+

OH
a

Symmetrical
 -i ! -
H
⑧
Il I Il
RHTRX
-

IR-O
no

Sert
0
Addition
-> I
·40
on o
r
=
0
Il
R X:
Ho
- ⑧
Il
Elimination
·
RX. O ⑧
-> It
II
RoR
-

- ->
R oX

H28
+

--
Symmetrical

Iotation, boot D IP Elimination

8

It
8. I
Wi
- / t
No
Nu
o
Leaving group like: *in x