Documente Academic
Documente Profesional
Documente Cultură
H H H H Br H
+
H3C C C H H3C C C H
Elimination of Halogenoalkanes with ethanolic
δ+ H hydroxide ions
H -:OSO
2OH H H H H
OSO 2OH
δ- CH3 C C H
H H CH3 C C H
+ Br - + H2O
H3C C C H Br H
H :OH-
OSO 2OH
H conc H2SO4 or
+
conc H3PO4 H
H H
+
H3C C Br H3C C NH3 Br -
H
H
3HN:
H H
+
H3C C NH2 H3C C NH2 + NH4Br
:NH3
H H H
The amine formed in the first reaction has a lone pair of electrons on the
nitrogen and will react further with the haloalkane.
H
+
H3C C Br H3C CH2 NH2 CH2 CH3 Br -
H
:
CH3CH2NH2
+
H3C CH2 NH CH2 CH3 H3C CH2 NH CH2 CH3 + NH4Br
:NH3
Diethylamine
H
H CH3
CH2
H3C C Br +
H3C CH2 NH CH2 CH3
H
:
H3C C Br CH3
CH2
H +
H3C CH2 N CH2 CH3
:
NO 2 O O
NO2+
+ C CH3
H
+ C CH3
H
+
NO 2 O
C
+ H+ CH3
Alcohol
room temp Primary
Nu add/elim
amide
H2O room temp
Nu add/elim
N Goalby chemrevise.org
4
Aromatic synthetic routes
NO2
conc nitric acid + NH2
conc sulphuric acid
NH CH3
Sn and HCl CH3Cl
reduction Nu sub
Electrophilic
substitution
CH3COCl
acyl chloride in the presence Nucleophilic add-el
of anhydrous aluminium
chloride catalyst
Electrophilic substitution O
NH C CH3
O H
C O
CH3
NaCN + H2SO4 C CN
Nu Add
CH3
NaBH4
Red Nu Add
H LiAlH4
reduction
O
OH
CH
CH3 C CH2 NH2
CH3
CH3CO2H + H2SO4
heat
esterification
O
H3C CH O C CH3
N Goalby chemrevise.org 5