Organic Reaction Mechanisms Overview
Organic Reaction Mechanisms Overview
Free-radical substitution
70
~
CHyCHz(Hz + -320 +
4H28 + C
CHzCHzCHz + 50 >
3(0 +
4H20
-
, ,
amine
M
CHzCHy CHzNHz
·
+ HBr
>
limited 110 amine
Oy 191
excesso
,
19)
1
CHzCHzCHeCN + kBr
N
② propagation CHz-CHz
⑧
·() CH CHyCHz
CHz HC) CHyCHz
heat
·
+ 3 =
>
NS
T
CHy + x + + (
-
·
+
of
A cat
combustion +
HUR
CHz-C
G
O -
CHz
↓
Electrophilic addition #
H-( H
H
Alkane
free-rad sub +
Brz/( +
UV light + HBr
~
Haloalkane ester <
! -
-
H & H -
C -
c
-
C -
H
ithr it
#
&
H-
CHzCHzCHeBr
Hzc CH
CHzCHzCHz
oNat
-
-
-
Hyd
=
20 major
↑
+
HO-CH3
S
7
Est // Con
(H20) or H product
M
M
+ alcohol
1 19 9
+ dilute acid/dilule alkali
. .
CHyOH) ↓
CHz CHBrCHz CONC
+ heat follow by
H
ABr
+
H2SO4 acidification
-
M
+
CHyOH St
-
or Conc
-
HyPOy j
pr
Lacid-base
red = name and mechanism of +
H20 I H
reaction H -
C ( H -
c -
C -
C -
Br
pink = reagents Salt
·
+
He 0 CO2 +
it it h
masore
blue = condition and catalyst
=
3
acdueente
green = by-products
-
minor
· Nucleophilic substitution
product
· CHyCHBrCHzBr
↑ Carboxylic acid neutrali
S salt
CH3 CHy
-
+
alkali +
H2011)
I 12
I fast I
·
-
sub T 1)
Syl-3 halvalkane HsC
t
CHzCHeCOOH
Bri
:
Bra
Her , Hy- + Br- S
Hs C C OH +
- -
redox
· or
e
g I
-
. 19
.
H
1) HX//kBr +
ConCHzP04 1/H2S04
E
E
reactive metal
, salt
+
Hz (g) is H its
- -
E =
+
H20
all sinenitrile
(
21 CHICH , CH, COOH
-
PCly +heat HH
+
HyPO4
E
nu hydroxynitrile It
fGeri
E I
Cha Ch (OH) ot
-
I
S
I &
carbon add from ch
2) SN2-Phaloalkane H -c -
c -
H >
-
>
-
H -
c -
C -
H
3)
P(lz ,
Litt of it
E
-
+ H() +
POCIs cyanide
⑤ 4)
50(1) + H(l
⑤
al
+ 50
,
- Hyd/NHy(l · OH- intermediate
+
dilute acid/dilute
agent g
& A
e S04
H Nucleophilic addition
. .
w V 1991
NHy
A
e
g. NaOH
i~
.
Alkene L H CN
Alcohol
-
Ot OH
-
j
on
Ela//Hydration hot steam (H20(g1) HzPOp cat -to
I
+ conc heat HyS
+
Hy)-I
.
+
<
CHzCH CH2
O >
Hsl-C-EN > =N
- -
-
CHzCHzCHiOH
=
ot↑ Hvocr
⑧
&
Eli//Dehydration (alcohol vapours + hot cat of Also Powder
it H
tion Hydroxynitriles
+
, ① nucleophilic attack ② protonation
Y
+
H20 concacide g
· Nail
or H ~
Soy
&
.
Haloalkane
.
·
theat
S
PHH acd .
19 20 alcohol
,
Creo orange
ox :
2, 4 -
BrackersS
I : -
green
carbonyl present test
Hs)-P-C-E
Cr2072 Cr3t
-
⑤ and
> =
deep-orange
Mno : purple colorless
or
Pani Ppt formed
. AgNOz(99) X(aq) > AgX(s) + -
+ No; 199)
->
,
·
diam
Eld Agt(aq) + X (aq) AgX(S)
-
⑳
MnO -Mn2t -
X
-
⑳ 7 Tppt =
halide
aldehyde and Ketone
o
L 1 present
jHOnC
OH USe
complete combustion :
Hy5C-CH distillation
I & dilute conc
alcohol +
0 >
(02 + H> 8
NHz
NHz
-
Testing
OX NA &
-
C ~
OH
I
OH H
I I
a
↓
·↑ acd KMn84
or
acd KiCryOf
-
~
Aldehyde HCN +
KCN
saldehyde
whiteppt =
creamppt =
CJ 199)
Bo 199)
dis
inso
dis
dis
eventio
theat
CHzCHzCOH
.
H C C C H
Ketones
-
↓
- - -
50(9) it i it L HUR + H , O
~
+ + H 0 pale yellowppt = I lag ) inso inso
carboxylic
Ketone Methyl Ketone co alcohol
.
+
,
containCr2+
+
Fehling solution
...
-
acid +...
2-did
1
iodoform//tri-iodomethane /CHIs
aldehyde * Carboxylic
,
~ acid Tollen's reagent contain -
Ag
+
L Hy) CHs neat with
- -
= NaOH (ag)
-
> theat
NaOH(ag) Fehling solution aldehyde carboxylic acid
neat with
*
akoxide Hz (9) W
+
RCOCHz ROCIs
brea-
RCOGNa
-
>
+
CHIs [u =
aldehydea
Tollen's
reagent silver mirror
while crystalline
solid carboxylic acid haloge clear
ppt. Agtr --
aldehyde
Naz coz effervescence (CO) yellow ppt formed methyl ketone present present
effervescence . =
carboxy) present
=
+ 20 alcohol