R-HC=CH2 xCO2 + yH2O

O2
R-C≡CH lete
combus
tion

H2/Pt Com
p
R3C-OH
Na- KMnO 4
D X2 / h𝝼
R-X
ry e
ther
R-X Wurtz
Rxn.
(steam)H O / Ni
CO + 3H2
2
H2 /Zn/H+ 𝚫
Anhy. AlCl / H
3 Cl

O H/
C aO Cr O
2 3 +A
l2 O /
Isomeric Alkanes
Na ion Aro 3 600 o
R-COOH
mat
lat i
zati C

arb
ox
y on
Aromatic Hydrocarbon
c
De b e’s sis Pyrolysis
l y
Ko trol
ec 770 K/Pt/Ni/Pd
El
R-COOH Alkenes + Alkanes
a Hydrogenation of alkenes/alkynes
Pt/Pd/Ni
H2C=CH2 + H2 CH3-CH3
Pt/Pd/Ni
H3C-C≡CH2 + H2 CH3-CH3

b Reduction of alkyl halides

Zn / H+
C2H5-Cl + H2 C2H6 + HCl
c Wurtz reaction of alkyl halides
Dry ether
CH3Br + 2Na + CH3Br C2H6 + 2NaBr

d Decarboxylation of carboxylic salts

CaO
CH3COONa + NaOH CH4 + Na2CO3
𝚫
e Kolbe’s method from salt of COOH

Electrolysis
CH3COONa + H2O C2H6 + CO2 + H2 +
NaOH
a Halogenation Starts a chain reaction
with many byproducts
hv
CH4 + Cl2 CH3Cl + HCl

b Combustion reaction

𝝙
CH4 + O2 CO2 + H2O
 c Oxidation
KMnO4
(CH3)3CH (CH3)3COH

d Isomerization
Anhy. AlCl3/HCl
CH3(CH2)4CH3 CH3CH(CH3)-(CH2)2-CH3 +

CH3CH2-CH(CH3)-CH2-CH3
e Aromatization

f Reaction with steam

Ni
CH4 + H2O CO + 3H2
g Pyrolysis
773 K
C6H14 C6H12 + H2

C4H8 + C2H6

C3H6 + C2H4 + CH4

 R-HC=CH2 xCO2 + yH2O
O2
R-C≡CH lete
combus
tion

H2/Pt Com
p
R3C-OH
Na- KMnO 4
D X2 / h𝝼
R-X
ry e
ther
R-X Wurtz
Rxn.
(steam)H O / Ni
CO + 3H2
2
H2 /Zn/H+ 𝚫
Anhy. AlCl / H
3 Cl

O H/
C aO Cr O
2 3 +A
Isomeric Alkanes
l2 O /
Na ion Aro 3 600 o
R-COOH ox
y lat mat
iz atio
n
C
Aromatic Hydrocarbon
c arb
De b e’s sis Pyrolysis
l y
Ko trol
ec 770 K/Pt/Ni/Pd
El
R-COOH Alkenes + Alkanes
R-C≡CH
Na-
liq. d / Pt + H2 Alkanes
NH Ni/P
Bi
rc
(Tr h R
3
X 2/CCl 4 RCHX-CHX
an ed
Pd s a uc
+C
aC
lke tion
ne HX R-CHX-CH3
Lin O/ ) ov
dla 3 Ba
SO ko vnik
(Ci r ’s ca 4
Mar
sa
lke talyst
ne ) HBr-Peroxide
alc. KOH Anti-Markovnikov R-CH2-CH2-Br
R-X
H2O/ H+
cold/dil
R-CH(OH)-CH3
SO 4 ./ alk.
. H KMnO
co nc 2

R-OH 4
Glycol(syn addition)
O
n
io

3
/Δ

at

Carbonyl
Zn/H
Zn

2O
ge

compounds
lo
ha

RCHX-CH2X
De
a Reduction of Alkynes

Birch Reduction
b Reduction of Alkyl halide with alc. KOH

alc. KOH
CH3-CH2-Cl CH2=CH2 + KCl + H2O

c Dehydration of Alcohol with conc. H2SO4

conc. H2SO4
CH3-CH2-OH CH2=CH2 + H2O
443K
d Dehalogenation of vicinal dihalides
 a Addition of Dihydrogen

Ni/Pt/Pd
H 3C CH CH2 + H2 H 3C CH2 CH3
Propene Propane

b Addition of Halogens

CCl4
CH3 CH CH2 + Br – Br CH3 CH CH2
Propene Br Br
1,2–Dibromopropane
 c Addition of HX (Markovnikov Addition)

d Addition of HBr (Anti-Markovnikov Addition)

e Addition of Water
 f Reaction with KMnO4

Cold, dil.
CH3 CH CH2 + H2O + [O] CH3 CH CH2
alk. KMnO4
Propene OH OH
Propane-1,2-diol
(propylene glycol)

Hot, Con.
CH3 CH CH2+ H2O + [O] CH3 C O + HC OH
alk. KMnO4
OH O
Ethanoic acid
g Ozonolysis
R-C≡CH
Na-
liq. d / Pt + H2 Alkanes
NH i/P
Bi
rc
(Tr h R
3
N
X 2/CCl 4
RCHX-CHX
an ed
Pd s a uc
+C
aC
lke tion
ne HX R-CHX-CH3
Lin O/ ) ov
dla 3 Ba
SO ko vnik
(Ci r ’s ca 4
Mar
sa
lke talyst
ne ) HBr-Peroxide
alc. KOH Anti-Markovnikov R-CH2-CH2-Br
R-X
H2O/ H+
cold/dil
R-CH(OH)-CH3
SO 4 ./ alk.
. H KMnO
co nc 2

R-OH 4
Glycol(syn addition)
O
n
io

3
/Δ

at

Carbonyl
Zn/H
Zn

2O
ge

compounds
lo
ha

RCHX-CH2X
De
R-CHX-CHX-R
H2 Alkanes
i / P d/Pt
N
alc
.K
OH l R-CX2-CX2-R
+N X2 /CC 4
aN
H
2

HX
R-CX2-CH2-R
2H2O
CaC2 Hg 2+/dil. H S
2 O
4 R-CO-CH2-R

Cyclic Polymerization
 a From Calcium Carbide
𝝙
CaCO3 CaO + CO2
𝝙
CaO + 3C CaC2 + CO

CaC2 + 2H2O Ca(OH)2 + C2H2

b From vicinal dihalide
 a Reduction

Pt/Pd/Ni Pt/Pd/Ni
HC≡CH + H2 H2C=CH2 C2H6
H2
b Addition of halogen
c Addition of hydrogen halide
d Isomerization
e Cyclic Polymerization
R-CHX-CHX-R H2 Alkanes
i / P d/Pt
N
alc
.K
OH l R-CX2-CX2-R
+N X2 /CC 4
aN
H
2
HX
R-CX2-CH2-R
2H2O
CaC2 Hg 2+/dil. H S
2 O4 R-CO-CH2-R
Cyclic Po
lymerizat
ion