CHM 2211 Chapter Notes - Chapter 25: Enol, Ethyl Acetoacetate, Decarboxylation
OH
:O :in
#
+:O :
|/ µ
enol E11
AAE
R:O :R
"
>~..o
R
enolate
OH :O ;
1-7 11 H
RN c-
~
←(eguabibrium
Rfavors )
enol Keto
*
at Omer S
.
- '+1 01
"
'
'
o
KR->lip -7111
mc- ac- an
B-di carbonyl -#
Eno )form
Compound favored Cconsugated )
(Keto )
Problem 23.1 ( convert to end ,,ne+o)
Problem
23.1 (Draw + automer )
OH a.zany
d. 0¥ a050
a. %-7 /N b. qq.it -0¥
't e. Onions @nx%
b'
¥
"
<-,#
aanswer <→ c. .see f.03
"°~°
='@t# +
*maybe go over + automerization
mechanism
*How Enols react ,good
•
they are electron rich (Nu )
• neutral product
kHz
-m%n
'
.ee#%ee.**ieE
*2is more acidic (remove
Pray
)
:8 :
:P :f. Bt
Base #g
<→In +Hat
.
AH -7 ^..0
RJth th
*2Still less acidic than OH
*formed from : aldehyde s
,
Ketches
,
esters ,
30 amides
-
Errol ate resonance
a
oo:E ::g ::O ::O:@
(111 I11 11 1
non -7 m2-7 X
0 6
Problem 23.4 ( Draw resonance )problem 23.5 (which C-H bonds are
acidic )
a.
ojekonaoijonon .,bi¥÷n °°
b. 0Ef¥< →OFF -0¥ ..
a'"~ b. ~w c. m" on
"OIL <→OIL .
d"o=Q=o (a carbon 's )
What Base ?
*
the Stringer the more Enolate forms
* equilibrium
-avors side with weaker
acid (higher Pka )
Conjugate acid >20 pka
=
-conjugate
II
'eigIer'
aua
.
Ketone
\>enaa+e The
.no#duc+
+
-
|Na
,
H
LLDAA
=
