IB Chemistry HL: A summary of all organic synthetic routes and the necessary reaction mechanisms (including benzene)

Synthetic routes
①
dihalogenoalkane alkene


= mechanism ②
required
=
Oxidation
=


- =
reduction/addition of He
addition
Alkane ④
=
substitution
⑤
& =
Condensation
* ~
C &
⑪ ester

halogenoalkane
D
Alcohol
O
6

↓O ↑-
>

⑦
> carboxylic
a

⑧
Ketone aldehyde # acid
Conditions:

① Electrophilic addition A ② Electrophilic addition/reduction (H2 added)
alkene
alkensdihalogenoalkane -> Alkane
-




④ Hydration
Room temperature hydrogen reagent
-
-




Nicker alkene Alcohol
Catalyst
- - >




*
°
-
200 C -

steam
-


1000 A -

H2SO4

③ Electrophilic addition A ⑤ Free radical substitution ⑧ Nudeophilic substitution

alkene -
Halogenoalkane alkane >
-


halogenokane halogenokane >
-
Alcohol

HYDROGEN HALIDE reagent E HBr halogen reagent * NaOH (aq) reagent *
- -




g
-


.




-

Room temperature -
UV
light
-



heat under reflux



⑦ Oxidation ⑧ Reduction ⑨ Oxidation ⑩ Reduction
alchol >
-

Ketone Ketone -
Alcoho Acohol-aldehyde Aldehyde
>
-

alcohol
-
heat -




NaBH4 (aq) -

(DISTILLATION)
Heat -


heat
-



k2(207/H2SO4 -

heat -




k2C207/H2SO4 -



NaBH4 (99)

⑪ Esterification/condensation ⑫ Reduction ⑬ Oxidation

Alcohol Carboxylic acid acid aldehyde
+ ester
carboxylic alcohol carboxylic acid
>
>
- >
-
-




-


H2SO4 Catalyst -

heat kzCr207/H2SO4
-




-
alchol +
carboxylic acid reagents
-



LiAIH in
dry ether
-

Heat under reflux


⑭ reduction
Carboxylicacia -

aldehyde
-


heat
-


LiAlpin dry ether

, Reaction mechanisms *

Q Electrophilic addition
alkene
dihalogenoalkane
-




donates pair of elections
primary Carbocation
+
to Br


↑is
↑




Y
n
↑ M I
M

>
H c c H H H
3 2
ETHENE
-
- - -
= - - -




S+
v
S-
Br Br Br
Br-Br
La
d
Electrophile


③ Electrophilic addition
alkene >
honogenoamane
-




donates a pair of Primaus

↑
-




electrons to H Carbocation

↳
H H
H


"In
H H
I I
c
I
C -

- >
-
H -
c -
c -
H -
n c -

c -
H

/
!
9



.
1

S +
8 -
↓ Br H Br
H -
Br


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