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Haloalkane

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4.

Haloalkane/Alkyl halide
aq NaOH/reflux CH3CH2OH (nucleophilic subst)
from
NaOH (or base)
Alkane
ethanolic NaOH CH2==CH2 + H2O + NaCl
CH3CH3
Cl2/uv reflux (elimination)
+
KCN/et, reflux H2O/H CH3CH2COOH
From alkene HCl CH3CH2CN heat
CH2==CH2 H2/Ni, 180 C or LiAlH4/ether
CH3 CH2Cl
CH3CH2CH2NH2
PCl3 or HCl Limited NH3 (CH3CH2)4N+
From alcohol or PCl5 or SOCl2 Conc. NH3/ethanol excess CH3CH2Cl
CH3CH2OH Heat excess NH3 CH3CH2NH2

Mg/dry ether CH3CH2MgX i. R--C==O CH3CH2C-- OH


Li/dry ether CH3CH2Li ii. H2O R

AgNO3/et CH3CH2OH + AgCl


(White ppt—test for alkyl halide)
AgBr—cream/pale yellow ppt
AgI---yellow ppt)
Alkene
CH2==CH2

Aq NaOH /refux
C2H4Br2 KCN/et, reflux
2 str. isomers
H
CH3—C--Br Aq NaOH/reflux
Br CH3CHO
Alkane
ethanolic NaOH/reflux
CH3CH3
5. Chlorobenzene
(i) aq NaOH/360 C, 200 atm (ii) H+
(or high temp. & high pressure)
Aq NaOH
Aq NaOH/reflux no reaction

Cl2 /anh AlCl3 AgNO3/et No observation


Li/dry ether Li
RCHO
Mg/dry ether MgCl H2O alcohol

Conc. HNO3/conc. H2SO4

Cl2/anh. AlCl3

CH3Cl/anh. AlCl3

(all electrophilic substitution reactions, halogen deactivates but directs


ortho and para)

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