Summary CHM136 CHEATSHEET - ALL REACTION MECHANISMS (4 pages)

Aldehydes & Ketones

C


r -




··
EtOR-MogBr
R- Br
H
4
m-

-·
11
H -




n
3



R
H
I
r > > O
↑
H




& CEN : cyanides 8
. CER acetylites > 2 1 Steric
>
-

hydroxynitriles -




~
. effects
.
2 Electronic effects
H20 aldehydes/kelones -

gem-diols

base catalysed lacid catalysed)
: H




) I 448 (0)
O
+ -
"
j t
-
>

- ↑J - -



ROH aldehydes/vetones hemiacetals/hemiketals I


1 R




Gig ·
gi
i
:




1 -
Homesteromen"no ·
OH

deprotonation
2




Carboxylic acit derivatives
thylchloride)
: acid
·
acyl chlorides charide
L




carboxylic acyl


T
CHC13

Ma
3




Nu
Ro an


↑j
chlorides acit anhytrites carboxylic acitslesters >amides
acyl = =




P
J
acyl chlorite i >

> amide + NH ,25
ammonium
↓ salt
-

c IV




R H



actanhydrideestert cabin its it (no base neetet)

, -




·
:
-




~



!
1




OR
·


Iron

(ea ].




Mr Each
↳
.




&
ROM (excess) o ester/carboxylic acid l
Il Il
Fischesterification
>
128
↑
-




on HCl cat Mor
+

.




~
MoBro
G




-Mar Ar
G
-
·n jeon = -
- - I



II -

R Mabr
Tr
-in
-




1




aldehyde name i

h
-




I
b
V




Kor/In >
8
↳

Kenen
- nor
-




n




-
-

G
T =


Norton +ron
8
!
1 II

( H , 8)

J
ROHrexcess
↑
Transesterification
-




Kor
>
-



same mechanism as
HCI cat .




above
g

Ester hydrolysis II
H20 /excess)
>
-
-↑ reverse
lacidic Mor #ICI cat .




S>
8 O


Mom
H

(basic) + RON

-

>
Om
-




Amine reduction




- N-An > -




N -
NH2

y H
HCI ↓
An
Amidehydrolysis
IH


-

j-
>
- + I


I H28 "

oniums




SHEAT z
NaOI
O >
-
>
-




(basic)
* o T famine)