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H

H C Br H

1. SYNTHESIS ROUTES INVOLVING ALKANES & ALKENES


H H C H H

Br2(l) in CCl4
H C Br

Cl2(g) uv or heat

H H C Cl H
H H C OH H

Br2(aq)
H C Br

methane

H H C H

H C Br H

alcoholic KOH heat

H C OH H

H2O (g)

H C C

300 C, 60 atm, conc. H3PO4

C H

H H C H

H C OH H

excess conc. H2SO4 170 C

ethene

H
H H C H H

H2(g) / Ni catalyst High T & High P


H C H

H
conc. KMnO4 / H+

C
heat

CO 2(g) + H2O(l)

H C OH H

cold, dilute KMnO4 / OH


H C OH CH3

H
R

R C H

conc. KMnO4 / H+
C O

H2O (g) 300 C, 60 atm, conc. H3PO4


HO

CH3 H C H

CH3 C OH

heat

H 3C
C O

CH3 C C CH3
HBr(g)
H

R C R

conc. KMnO4 / H+ heat


R

CH3 C H

CH3 C Br CH3

2-methylbut-2-ene

SYNTHESIS ROUTES INVOLVING ARENES


CH3

CH3
conc. HNO3 / conc. H2SO4 Br2 FeBr3 30 C

NO2

Br

NO2
CH3Cl AlCl3

CH3
benzene
conc. HNO3 / conc. H2SO4 60 C Br2

CH3 Br

CH3

NO2

FeBr3

methylbenzene
Br
1. Sn / conc. HCl, heat 2. NaOH(aq)

CH2Cl
Cl2(g) uv

NH2

COOH
KMnO4 / H+ heat or 1) KMnO4 / OH , heat 2) H+

SYNTHESIS ROUTES INVOLVING HALOGENOALKANES


NaOH(aq)

CH3 H C H OH

CH3 H C H H

Br2(l) uv

heat

alcoholic KOH

H C H C

H C H C

CH3
HBr(g)

heat

C H

Br

bromoethane
excess conc. NH3

CH3 H C H NH2

CH3
PBr3

heat in sealed tube

C H

OH

heat

*If PCl5 is used, no heat is required*

alcoholic KCN heat

CH3 H C H CN

LiAlH4 dry ether

CH3 H C H CH2NH2

CH3 H C H COO Na

NaOH(aq) heat

H2SO4(aq) heat

CH3 H C H COOH

SYNTHESIS ROUTES INVOLVING ALCOHOLS


H

CH3 C H Cl

Other chlorinating reagents: SOCl2, PCl3, HCl with ZnCl2

CH3 H C H
PBr3 heat

Br

Other brominating reagent: NaBr with conc. H2SO4

H C H C

1. conc. H2SO4 , r.t. PCl 5 (s) 2. steam

PI3 heat

CH3 H C H
K2Cr2O7(aq) / H+ heat with distill

O H3C C H

CH3 H C H Br

NaOH(aq) heat

CH3 H C H ethanol OH
K2Cr2O7(aq) / H+ or KMnO4 / H+ heat heat

O H3C C OH

O H3C C H

LiAlH4 dry ether

excess conc. H2SO4 I2(aq) / NaOH 170 C heat

H C H C

O H3C C OH

LiAlH4 dry ether

carboxylic acid + conc. H2SO4 + heat or acid chloride

O R C O CH2CH3

O H C O CHI3

Na(s)

CH3 H C H O Na

Na

SYNTHESIS ROUTES INVOLVING PHENOLS


OH
Br2(l) in CCl4

O Na
Na(s) or NaOH(aq)

Br

OH

OH
Br
Br2(aq) room temperature

Br

phenol

Br

O C O R
Cl

O C R acid chloride

OH

OH
dil. HNO3(aq)

NO2

NO2

SYNTHESIS ROUTES INVOLVING ALDEHYDES


LiAlH4 dry ether

H H3 C C H OH

K2Cr2O7(aq) / H+ heat

O H3C C OH

H
K2Cr2O7(aq) / H+

O H3C C H
ethanal
2,4-dinitrophenylhydrazine

H 3C C H N N H O 2N NO2

H3C

C H

OH

heat with distill

HCN with trace KCN

OH H3 C C H CH2NH2
LiAlH4 dry ether

OH H3 C C H CN

NaOH(aq) heat

OH H3C C H
dil H2SO4(aq)

COO Na

dil H2SO4(aq) heat

OH H 3C C H COOH

SYNTHESIS ROUTES INVOLVING KETONES


LiAlH4 dry ether

H H3C C CH3 OH

O
I2(aq) / NaOH heat

H 3C

C O

CHI3

Na

H
K2Cr2O7(aq) / H+

H3C

C CH3

OH

H3C

C CH3

2,4-dinitrophenylhydrazine

heat

H3C C H3C
HCN with trace KCN

propanone

N H O 2N

NO2

OH
LiAlH4

OH
CH2NH2

NaOH(aq)

OH H3C C CH3
dil H2SO4(aq)

H3C

C CH3

dry ether

H3C

C CH3

CN

heat

COO Na

dil H2SO4(aq) heat

OH H3C C CH3 COOH

SYNTHESIS ROUTES INVOLVING CARBOXYLIC ACIDS


conc. KMnO4 / H+ heat LiAlH4 dry ether

H H3 C C H OH

H3C C H C

CH3

H H3C C H
O H3C C H

K2Cr2O7(aq) / H+ PCl 5(s)

O H 3C C Cl

OH

heat

K2Cr2O7(aq) / H+ heat

O H3C C OH
ethanoic acid
Na(s) or NaOH(aq) or Na2CO3(aq)

O H3C C

+ H2 (if reacts with Na) + CO2 (if reacts with Na2CO3) + H2O (if react with NaOH)

O Na

H H C H CN

H2SO4(aq) heat CH3CH2OH heat with conc. H2SO4 H2O(l)

O H3C C O CH2CH3

O H 3C C Cl

NH3(aq)

O H3C C O NH4

O H3C C O CH2CH3

H2SO4(aq), heat or NaOH(aq), heat followed by addition of H2SO4(aq)

H2O(l)

O H3C C OH

+ HCl (g)

SYNTHESIS ROUTES INVOLVING ACID CHLORIDES


NaOH(aq)

O H3C C O Na

CH3CH2OH

O H3C C O

+ HCl (g)

O H3C C OH
PCl 5(s)

O H3C C Cl
ethanoyl chloride
HO

CH2CH3

, NaOH

O H3C C O

or

O
NH3(l)

H3C

C NH2

+ HCl (g)

O
CH3NH2 (l)

H3C

C N H
amide

CH3

10

SYNTHETIC ROUTES INVOLVING NITROGEN COMPOUNDS


CH3Br

CH3 H C H
CH3CO2H

N H

CH3

CH3 H C H
CH3

Br

excess conc. NH3 heat in sealed tube

CH3 H C H NH3 O

O C CH3

CH 3

CN

LiAlH4 dry ether

C H

NH2
CH3
HCl(aq)

ethylamine
LiAlH4 dry ether

C H

NH3 Cl

O H3C
NaOH(aq) heat

C NH2
ethanamide

CH3
CH3COCl

O N H
amide

dil H2SO4(aq) heat

C H

CH3

NO2
O H3C C O Na NH3 H3C C OH O NH4
1. Sn / conc. HCl, heat 2. NaOH(aq)

NH2
Br
Br2(aq)

NH2 Br

phenylamine

Br

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