Organic Chemistry Compiled by Saya Minn Thant

SAYA MINN THANT (B.Ed.
) ORGANIC CHEMISTRY
Chapter (14)
ORGANIC CHEMISTRY
What is organic chemistry?
Organic chemistry is the chemistry of carbon compounds in which there
is at least one carbon bond (C-C) or carbon to hydrogen bond (C-H).
bond order of carbon =4
bond order of hydrogen = 1
Bond orders in organic compounds

element electronic valence bond order
structure electrons (valence)
6C 2.4 4 4
1H 1 1 1
8O 2.6 6 2
7N 2.5 5 3
16S 2.8.6 6 2
halogens ns2 np5 7 1
15P 2.8.5 5 3
Graphic formulae
H H H H
H C H N H H C C H
-
H H H H
methane ammonia ethane
Hydrocarbons are compounds which contain hydrogen and carbon only.
alkane alkene alkyne

Hydrocarbons
alkane saturated unsaturated unsaturated

hydrocarbon hydrocarbon hydrocarbon
alkene single bond ( ) double bond ( ) triple bond ( )
CnH2n+2 CnH2n CnH2n-2
alkyne
substitution addition reaction addition and
reaction substitution
reaction
Page 1 Organic Chemistry

SAYA MINN THANT (B.Ed.) ORGANIC CHEMISTRY
Prefixes for various numbers of carbon

C1 meth- C2 eth- C3 prop- C4 but- C5 pent-
C6 hex- C7 hept- C8 oct- C9 non- C10 dec-
Alkanes (ending with –ane)

type of hydrocarbon = saturated hydrocarbon
type of bond = single bond ( - )
general formula = CnH2n+2
type of reaction = substitution reaction
Homologous Series
A series of compounds like alkanes in which each member differs
from the preceding or succeeding one by a (-CH2-) group is known as
homologous series.
Homologous Series (Molecular Formulae and Names) of Alkanes

CH4 methane C6H14 hexane
C2H6 ethane C7H16 heptane
C3H8 propane C8H18 octane
C4H10 butane C9H20 nonane
C5H12 pentane C10H22 decane
Condensed structural Formulae of Alkanes

(i) methane = CH4
(ii) ethane = CH3-CH3
(iii) propane = CH3-CH2-CH3
(iv) butane = CH3-CH2-CH2-CH3
Try yourself from C5 to C10 .
3D models of hydrocarbons
methane ethene ethyne ethanol

CH4 CH2=CH2 CH CH CH3-CH2OH
Alkyl Radicals (R- Groups) (ending with –yl)

The radicals derived from alkanes by the removal of an H atom are
called alkyl radicals or groups. (R- = CnH2n+1)
−𝑯
CnH2n+2 → CnH2n+1
−𝑯
(i) CH4 → CH3-
methane methyl
−𝑯
(ii) CH3-CH3 → CH3-CH2-
ethane ethyl
−𝑯
(iii) CH3-CH2-CH3 → CH3-CH2-CH2-
propane n-propyl
(OR)
CH3-CH-CH3 (OR) CH3-CH
iso-propyl CH3
−𝑯
(iv) CH3-CH2-CH2-CH3 → CH3-CH2-CH2-CH2-
n-butane n-butyl
(OR)
CH3-CH2-CH-CH3
sec-butyl
CH3 CH3 CH3
−𝑯
(v) CH3-CH-CH3 → CH3-CH-CH2- (OR) CH3-C-CH2
iso-butane iso-butyl ter-butyl

Isomers
The compounds of same molecular formula but different structural
formulae are called structural isomers. They have different physical and
chemical properties.eg. two isomers of butane = n-butane and iso-butane
Molecular formula Structural formulae

CH3-CH2-CH2-CH3
C4H10 (n-butane)
CH3-CH-CH3
CH3
2-methyl propane (iso-butane)
CH3-CH2-CH=CH2
1-butene (α-butylene)
C4H8 CH3-CH=CH-CH3
2-butene (β-butylene)
CH3-C=CH2
CH3
2-methyl propene (iso-butylene)
CH3-CH2-C≡CH
C4H6 1-butyne (ethyl acetylene)
CH3-C≡C-CH3
2-butyne (dimethyl acetylene)
Energy and persistence conquer all things.

-Benjamin Franklin-

Nomenclature of Alkanes
Three different naming systems are currently in use. They are;
(1) Trivial System
(2) Alkanes as derivatives of methane
(3) IUPAC System (or) Geneva System
The word ‘IUPAC’ stands for ‘International Union of Pure and
Applied Chemistry’.
(1) Trivial System

Trivial System အရ carbon atom သံုးလံုးထက္ပိုတဲ့ alkane ေတြကို အမည္ေပးတဲ့အခါ
- Carbon atom အားလံုး တစ္တန္းတည္းျဖစ္ေနလွ်င္ n-alkane
- Carbon atom တစ္လံုးကို CH3အုပ္စုႏွစ္ခု တိုက္ရိုက္ဆက္ထားလွ်င္ iso-alkane
- Carbon atom တစ္လံုးကို CH3အုပ္စုသံုးခုတိုက္ရိုက္ဆက္ထားလွ်င္ neo-alkane
(i) CH4 = methane
(ii) CH3-CH3 = ethane
(iii)CH3-CH2-CH3 = propane
(iv) CH3-CH2-CH2-CH3 = n-butane
(v) CH3-CH-CH3 = iso-butane
CH3
(vi) CH3-CH2-CH2-CH2-CH3 = n-pentane
CH3-CH-CH2-CH3 = iso-pentane
CH3
CH3
CH3-C-CH3 = neo-pentane
CH3
(2) Alkanes as derivatives of methane
(i) CH4 = methane
(ii) CH3-CH3 = methyl methane
(iii) CH3-CH2-CH3 = dimethyl methane
(iv) CH3-CH2-CH2-CH3 = ethyl methyl methane
(v) CH3-CH-CH3 = trimethyl methane
CH3

(vi) CH3-CH2-CH2-CH2-CH3 = diethyl methane

(vii) CH3
CH3-CH-CH2-CH3 = ethyl dimethyl methane
(viii) CH3
CH3-C-CH3 = tetramethyl methane
CH3
(3) IUPAC System or Geneva System
IUPAC System အရ carbon atom သံုးလံုးထက္ပိုတဲ့ alkane ေတြကို အမည္ေပးတဲ့အခါ
- အ႐ွည္ဆံုး carbon chain (ကာဗြန္ဆက္တန္း)ကို ႐ွာ
- substituent (အစားထိုးအုပ္စု)ႏွင့္ အနီးဆံုးအစြန္ကစၿပီး carbon နံပါတ္တပ္္
- မ်ိဳးတူ substituent တစ္ခုထက္ပိုလွ်င္ di, tri, tetra ထည့္
- မ်ိဳးမတူ substituent မ်ားအတြက္ အဂၤလိပ္အကၡရာအစဥ္အတိုင္းေရး
- အ႐ွည္ဆံုး carbon chain (ကာဗြန္ဆက္တန္း)ကို -ane ႏွင့္ အဆံုးသတ္
- ဂဏန္းႏွစ္လံုးၾကား comma (,) ျခား၊ ဂဏန္းႏွင့္ စာၾကား dash (-) ျခားေပး
(i) CH4 = methane
(ii) CH3-CH3 = ethane
(iii) CH3-CH2-CH3 = propane
(iv) CH3-CH2-CH2-CH3 = n-butane
1
(v) CH3-2CH-3CH3 = 2-methyl propane
CH3
(vi) 1CH3-2CH-3CH2-4CH3 = 2-methyl butane
CH3
(vii) CH3
1
CH3-2CH-3CH-4CH2-5CH3 = 2,3-dimethyl pentane
CH3
(viii) CH3
1
CH3-2C-3CH2-4CH3 = 2,2-dimethyl butane
CH3
(ix) CH3
4
CH3-3CH -2C-1CH3 = 2,2,3-trimethyl butane
CH3 CH3

(x) CH3
1
CH3-2CH-3CH2-4CH-5CH2-6CH3 = 4-ethyl 2-methyl hexane
CH2-CH3
Alkenes (ending with –ene)
type of hydrocarbon = unsaturated hydrocarbon
type of bond = double bond ( = )
general formula = CnH2n
type of reaction = addition reaction
Homologous Series (Molecular Formulae and Names) of Alkenes
C2H4 ethene C7H14 heptene
C3H6 propene C8H16 octene
C4H8 butane C9H18 nonene
C5H10 pentene C10H20 decene
C6H12 hexene
Condensed Structural Formulae of Alkenes
(i) ethene = CH2=CH2
(ii) propene = CH3-CH=CH2
(iii) butene = CH3-CH=CH-CH3 (or)
CH2=CH-CH2-CH3
Nomenclature of Alkenes
Three different naming systems are currently in use. They are;
(1) Trivial System
(2) Alkenes as derivatives of ethylene
(1) Trivial System

Alkene မွ -ene ကိုျဖဳတ္ -ylene ျဖင့္ အဆံုးသတ္ေပး
(i) CH2=CH2 = ethylene
(ii) CH3-CH=CH2 = propylene
(iii) CH3-CH2-CH=CH2 = α-butylene (1-butylene)
CH3-CH=CH-CH3 = β-butylene (2-butylene)
(iv) CH3
CH3-C=CH2 = iso-butylene
Notes
−𝑯 −𝑯
CH4 → CH3- → CH2=
methane methyl methylidene
−𝑯 −𝑯
CH3-CH3 → CH3-CH2- → CH3-CH=
ethane ethyl ethylidene
−𝑯
CH2=CH2 → CH2=CH-
ethene ethenyl (vinyl)
(2) Alkenes as derivatives of ethylene
(i) CH2=CH2 = ethylene
(ii) CH3-CH=CH2 = methyl ethylene
(iii) CH3-CH2-CH=CH2 = ethyl ethylene
(iv) CH3-CH=CH-CH3 = s-dimethyl ethylene
(v) CH3-C=CH2 = uns-dimethyl ethylene
CH3
(3) IUPAC System or Geneva System.
IUPAC System အရ carbon atom သံုးလံုးထက္ပိုတဲ့ alkene ေတြကို အမည္ေပးတဲ့အခါ
- double bond ပါေသာ အ႐ွည္ဆံုး carbon chain (ကာဗြန္ဆက္တန္း)ကို ႐ွာ
- double bond ႏွင့္ အနီးဆံုး အစြန္ကစၿပီး carbonနံပါတ္တပ္
- double bondပါေသာ အ႐ွည္ဆံုး carbon chain (ကာဗြန္ဆက္တန္း) ကို double
bond ႐ွိေသာ carbonနံပါတ္ႏွင့္တြဲၿပီး -ene ႏွင့္ အဆံုးသတ္
- ဂဏန္းႏွစ္လံုးၾကား comma (,) ျခား၊ ဂဏန္းႏွင့္ စာၾကား dash (-) ျခား
(i) CH2=CH2 = ethene

(ii) CH3-CH=CH2 = propene
4
(iii) CH3-3CH2-2CH=1CH2 = 1-butene
1
(iv) CH3-2CH=3CH-4CH3 = 2-butene

(v) CH3
3
CH3-2C=1CH2 = 2-methyl propene
(vi) CH3
5
CH3-4C-3CH=2CH-1CH3 = 4,4-dimethyl 2-pentene
CH3
(vii) CH3 CH3
7
CH3-6C-5CH2-4CH-3CH2-2CH=1CH2
CH3
4,6,6-trimethyl 1-heptene
(viii) CH3 CH2-CH3
5
CH3-4C - 3C-2CH=1CH2
CH3 CH2-CH3
3,3-diethyl 4,4-dimethyl 1-pentene
(ix) CH2-CH3
6
CH3-5CH-4C-CH3
CH3-CH2-3C-CH3
2
CH=1CH2
3,4-diethyl 3,4-dimethyl 1-hexene
(x) CH2-CH3 CH3
1
CH2=2CH-3C-4CH2 - 5C-6CH2-7CH3
CH3 CH2-CH3
3,5-diethyl 3,5-dimethyl 1-heptene
Alkynes (ending with –yne)
type of hydrocarbon = unsaturated hydrocarbon
type of bond = triple bond (≡)
general formula = CnH2n-2
type of reaction = addition and substitution reaction
Homologous Series (Molecular Formulae and Names) of Alkynes
C2H2 ethyne C7H12 heptyne
C3H4 propyne C8H14 octyne
C4H6 butyne C9H16 nonyne
C5H8 pentyne C10H18 decyne
C6H10 hexyne
Condensed Structural Formulae of Alkynes

(iv) ethyne = CH ≡ CH
(v) propyne = CH3- C ≡ CH
(vi) 1-butyne = CH3-CH2-C ≡ CH
2-butyne = CH3-C ≡ C-CH3
Nomenclature of Alkynes
Two different naming systems are currently in use. They are;
(1) Trivial System (derivatives of acetylene)
(1) Trivial System (derivatives of acetylene)
(i) CH ≡ CH = acetylene
(ii) CH3- C ≡ CH = methyl acetylene
(iii) CH3-CH2-C ≡ CH = ethyl acetylene
(iv) CH3-C ≡ C-CH3 = dimethyl acetylene
IUPAC System အရ carbon atom သံုးလံုးထက္ပိုတဲ့ alkyne ေတြကို အမည္ေပးတဲ့အခါ
- triple bond ပါေသာ အ႐ွည္ဆံုး carbon chain (ကာဗြန္ဆက္တန္း)ကို ႐ွာ
- triple bond ႏွင့္ အနီးဆံုး အစြန္ကစၿပီး carbonနံပါတ္တပ္
- triple bond ပါေသာ အ႐ွည္ဆံုး carbon chain (ကာဗြန္ဆက္တန္း) ကို triple
bond ႐ွိေသာ carbonနံပါတ္ႏွင့္တြဲၿပီး -yne ႏွင့္ အဆံုးသတ္
(i) CH ≡ CH = ethyne
(ii) CH3- C ≡ CH = propyne
4
(iii) CH3-3CH2-2C ≡1CH = 1-butyne
1
(iv) CH3-2C ≡ 3C-4CH3 = 2-butyne

(v) CH3
4
CH3-3CH-2C ≡ 1CH = 3-methyl 1-butyne
(vi) 5CH3-4CH-3CH-2C ≡ 1CH = 3-ethyl 4-methyl 1-pentyne
CH3 CH2-CH3
(vii) CH3 CH3
6
CH3-5C -4C-3C ≡2C-1CH3 = 4,4,5,5-tetramethyl 2-hexyne
CH3 CH3
(viii) CH3
5
CH3-4CH-3CH-2C ≡ 1CH = 3,4-dimethyl 1-pentyne
CH3
(ix) CH2-CH3
4
CH3-3C-2C ≡ 1CH = 3,3-dimethyl 1-pentyne
CH3
(x) CH3
6
CH3-5CH2-4C-CH2-CH3 = 3,4-diethyl 3,4-dimethyl 1-hexyne
CH3-CH2- 3C-CH3
1
CH ≡ 2C
Alcohol (ending with –ol)
general formula = CnH2n+1OH (or) CnH2n+2O
Homologous Series (Molecular Formulae and Names) of Alcohols
methanol CH3OH propanol C3H7OH
ethanol C2H5OH butanol C4H9OH
Condensed Structural Formulae of Alcohols
(i) methanol = CH3-OH
(ii) ethanol = CH3-CH2-OH
(iii) propanol = CH3-CH2-CH2-OH
(iv) butanol = CH3-CH2-CH2-CH2-OH
Nomenclature of Alcohols
Two different naming systems are currently in use. They are;
(1) Trivial System
(1) Trivial System (alkyl alcohol)

(i) CH3-OH = methyl alcohol
(ii) CH3-CH2-OH = ethyl alcohol
(iii) CH3-CH2-CH2-OH = n-propyl alcohol
CH3-CHOH-CH3 = iso-propyl alcohol
(iv) CH3-CH2-CH2-CH2-OH = n-butyl alcohol
CH3-CH2-CH2OH-CH3 = secondary butyl alcohol
CH3-CH-CH2OH = iso-butyl alcohol
CH3
CH3
CH3-C-OH = tertiary butyl alcohol
CH3
OH ႐ွိတဲ့ carbonဟာ တျခား carbon တစ္လံုးနဲ႔ဆက္ေနရင္ primary alcohol
ႏွစ္လံုးနဲ႔ ဆက္ေနရင္ secondary alcohol။ သံုးလံုးနဲ႔ ဆက္ေနရင္ tertiary alcohol

IUPAC System အရ carbon atom ႏွစ္လံုးထက္ပိုတဲ့ alcohol ေတြကို အမည္ေပး တဲ့အခါ
- OH ပါေသာ အ႐ွည္ဆံုး carbon chain (ကာဗြန္ဆက္တန္း)ကို ႐ွာ
- OH ႏွင့္ အနီးဆံုး အစြန္ကစၿပီး carbonနံပါတ္တပ္
- OH ပါေသာ အ႐ွည္ဆံုး carbon chain (ကာဗြန္ဆက္တန္း) အတိုင္း alkane က
-e ကိုျဖဳတ္ၿပီး -ol ႏွင့္ အဆံုးသတ္
- C3 မွစ၍ OHရွိေသာနံပါတ္ကို -olႏွင့္ ေရွ႕မွ တြဲေရး (သို႔) alcohol ေရွ႕မွေရး
(i) CH3-OH = methanol
(ii) CH3-CH2OH = ethanol
3
(iii) CH3-2CH2-1CH2OH = propan-1-ol (1-propanol)
3
(iv) CH3-2CHOH-1CH3 = propan-2-ol (2-propanol)
4
(v) CH3-3CH2-2CH2-1CH2OH = butan-1-ol (1-butanol)
4
(vi) CH3-3CH2-2CHOH-1CH3 = butan-2-ol (2-butanol)
(vii) 3CH3-2CH-1CH2OH = 2-methyl propan-1-ol

CH3 (2-methyl 1-propanol)
(viii) CH3
1
CH3-2C-OH = 2-methyl propan-2-ol
3
CH3 (2-methyl 2-propanol)
(ix) 4CH3-3CH-2CHOH-1CH3 = 3-methyl butan-2-ol
CH3 (3-methyl 2-butanol)
(x) CH3
6
CH3-5CH2-4C - 3CH-2CH2-1CH2OH
CH3 CH3
3,4,4-trimethyl hexan-1-ol (3,4,4-trimethyl 1-hexanol)
Notes: OH တစ္လံုးပါရင္ alcohol၊ ႏွစ္လံုးပါရင္ glycol
Nomenclature of organic acids

R-COOH (carboxylic acid or alkanoic acid)
Alkane မွ -e ကို ျဖဳတ္ၿပီး -oic ႏွင့္ အဆံုးသတ္ေပးပါ။
(i) H-COOH = methanoic acid (formic acid)
(ii) CH3-COOH = ethanoic acid (acetic acid)
(iii) CH3-CH2-COOH = propanoic acid
Nomenclature of organic salts
R-COONa (sodium salt of carboxylic acid or sodium alkanoate)
Alkane မွ -e ကို ျဖဳတ္ၿပီး -oate ႏွင့္ အဆံုးသတ္ေပးပါ။
(i) HCOONa = sodium methanoate
(ii) CH3-COONa = sodium ethanoate
(iii) CH3-CH2-COONa = sodium propanoate
Nomenclature of aldehydes
R-CHO (aldehyde or alkanal)
Alkane မွ -e ကို ျဖဳတ္ၿပီး -al ႏွင့္ အဆံုးသတ္ေပးပါ။
(i) H-CHO = methanal (formaldehyde)
(ii) CH3-CHO = ethanal (acetaldehyde)
Hexane C6H14

Preparations, Physical Properties and

Chemical Properties of Hydrocarbon
Preparations of alkanes
(1) heating sodium salt of carboxylic acid with soda lime
(2) reduction of alkyl halide
i. with hydrogen halide
ii. with hydrogen
(3) reduction of alkene (hydrogenation)
(1) Heating sodium salt of carboxylic acid with soda lime
soda lime = NaOH+CaO
R-COONa + NaOH CaO R-H + Na2CO3

sodium alkanoate alkane
CH3COONa + NaOH CaO CH4 + Na2CO3
sodium ethanoate methane
CH3-CH2COONa + NaOH CaO CH3-CH3 + Na2CO3
sodium propanoate ethane
(2) Reduction of alkyl halides
i. Reduction of alkyl halides with hydrogen halide (Hydro-
halogenation)
R-X + HX → R-H + X2
alkyl halide alkane
CH3I + HI → CH4 + I2
methyl iodide methane
CH3-CH2I + HI → CH3-CH3 + I2
ethyl iodide ethane
ii. Reduction of alkyl halides with hydrogen using platinum (Pt) or
palladium (Pd) catalyst (Hydrogenation)
𝑃𝑡 𝑜𝑟 𝑃𝑑
R-X + H2 → R-H + HX
alkyl halide alkane

CH3I + H2 → CH4 + HI
methyl iodide methane
CH3-CH2I + H2 → CH3-CH3 + HI
ethyl iodide ethane
(3) Reduction of alkene with hydrogen using nickel catalyst at 3000C
(Hydrogenation)
R-CH=CH2 + H2 𝑁𝑖,3000𝐶 R-CH2-CH3
→
alkene alkane
CH2=CH2 + H2 𝑁𝑖,3000𝐶 CH3-CH3
→
ethene ethane
CH3-CH=CH2 + H2 𝑁𝑖,3000𝐶 CH3-CH2-CH3
→
propene propane
CH3-CH2-CH=CH2 + H2 →𝑁𝑖,3000𝐶 CH3-CH2-CH2-CH3
1-butene n-butane
CH3-CH=CH-CH3 + H2 →𝑁𝑖,3000𝐶 CH3-CH2-CH2-CH3
2-butene n-butane
Physical Properties of Alkanes
C1 to C4 = colourless gases
C5 to C17 = colourless liquids
C18 and above = solids
Boiling points, melting points, viscocity and refractive indexes
increase as the numbers of carbon atoms increase.
Chemical Properties of Alkanes

(1) Combustion of alkanes
(2) Substitution reaction or Chlorination


Alkanes can burn in air and give water and carbon dioxide.
∆
CH4 + 2O2 → CO2 + 2H2O
methane
(2) Substitution reaction or Chlorination
Chlorination may be brought about by light, heat or catalyst.
CH4 + Cl2 𝑑𝑖𝑓𝑓𝑓𝑢𝑠𝑒𝑑
→
𝑠𝑢𝑛𝑙𝑖𝑔ℎ𝑡
CH3Cl + HCl
methane methyl
chloride
CH3Cl + Cl2 𝑑𝑖𝑓𝑓𝑓𝑢𝑠𝑒𝑑
→
CH2Cl2 + HCl
methylene
chloride
CH2Cl2 + Cl2 𝑑𝑖𝑓𝑓𝑓𝑢𝑠𝑒𝑑
→
CHCl3 + HCl
chloroform
CHCl3 + Cl2 𝑑𝑖𝑓𝑓𝑓𝑢𝑠𝑒𝑑
→
CCl4 + HCl
carbon
tetrachloride
Preparations of alkenes
(1) Dehydration of alcohols
i. Heating alcohol with concentrated sulphuric acid at 1600C
ii. Passing alcohol vapour over alumina catalyst heated at 3500C
(2) Dehydrohalogenation of alkyl halide
(1) Dehydration of alcohol
Two stages
0𝐶
R-CH2-CH2OH + H2SO4 100
→
R-CH2-CH2SO4H + H2O
alcohol alkyl hydrogen
sulphate
R-CH2-CH2SO4H 1600𝐶
→
R-CH=CH2 + H2SO4
alkene

One stage
𝑯𝟐 𝑺𝑶𝟒 (𝒄𝒐𝒏𝒄)
R-CH2-CH2OH → R-CH=CH2 + H2O
0
alcohol 160 𝐶 alkene
0𝐶
CH3-CH2OH + H2SO4 100
→
CH3-CH2SO4H + H 2O
ethanol ethyl hydrogen
sulphate
1600𝐶
CH3-CH2SO4H → CH2=CH2 + H2SO4
alkene
CH3-CH2OH → CH2=CH2 + H2O
0
160 𝐶
ethanol alkene
CH3-CH2-CH2OH → CH3-CH=CH2 + H2O
0
160 𝐶
propan-1-ol propene
CH3-CHOH-CH3 → CH3-CH=CH2 + H2 O
1600 𝐶
propan-2-ol propene
ii. passing alcohol vapour over alumina catalyst heated at 3500C
𝑨𝒍𝟐 𝑶𝟑
alcohol 𝟑𝟓𝟎𝟎 𝑪 alkene
CH3-CH2OH →
𝟎
CH2=CH2 + H2O
𝟑𝟓𝟎 𝑪
ethanol ethene
CH3-CH2-CH2OH →
𝟎
CH3-CH=CH2 + H2O
𝟑𝟓𝟎 𝑪
propan-1-ol propene
CH3-CHOH-CH3 → CH3-CH=CH2 + H2 O
𝟑𝟓𝟎𝟎 𝑪
propan-2-ol propene
Heating alkyl halide with an alcoholic solution of potassium
hydroxide on a water bath
ethanol
R-CH2-CH2X + KOH R-CH2=CH2 + KX + H2O
alkyl halide alkene

ethanol
CH3-CH2Cl + KOH CH2=CH2 + KCl + H 2O
ethyl chloride ethene
ethanol
CH3-CH2-CH2Cl + KOH CH3- CH=CH2 + KCl + H2O
n-propyl chloride propene
ethanol
CH3-CHCl-CH3 + KOH CH3- CH=CH2 + KCl + H2O
iso-propyl chloride propene
Physical Properties of Alkenes

C2 to C4 = gases
C5 to C15 = liquid
C16 and above = solids at room temperature and
insoluble in water
Chemical Properties of Alkenes
(1) Combustion of alkenes
(2) Addition reaction
i. Hydrogenation (addition of hydrogen)
ii. Halogenation (addition of halogen)
iii. Hydrohalogenation (addition of hydrogen halide)
(a) Symmetrical alkenes (one product)
(b) Unsymmetrical alkenes (two products)
(3) Ozonolysis (formation of ozonide)
(4) Hydroxylation of alkene
(5) Polymerization of alkene
Alkenes can burn in air and give water and carbon dioxide.
∆
CH2=CH2 + 3O2 → 2CO2 + 2H2O
methane
i. Hydrogenation (Addition of hydrogen)
Using nickel catalyst heated at 200-3000C
R-CH=CH2 + H2 𝑁𝑖,200−3000𝐶 R-CH2-CH3
→
alkene alkane

Using platinum or palladium catalyst

R-CH=CH2 + H2 → R-CH2-CH3
alkene alkane
CH2=CH2 + H2 𝑁𝑖,200−3000𝐶 CH3-CH3
→
ethene ethane
CH3-CH=CH2 + H2 𝑁𝑖,200−3000𝐶 CH3-CH2-CH3
→
propene propane
CH2=CH2 + H2 → CH3-CH3
ethene ethane
CH3-CH=CH2 + H2 → CH3-CH2-CH3
propene propane
ii. Halogenation (Addition of halogen)
R-CH=CH2 + X2 → R-CHX-CH2X
alkene alkene dihalide
CH2=CH2 + Cl2 → CH2Cl-CH2Cl
ethene ethene dichloride
(1,2-dichloro ethane)
CH3-CH=CH2 + Cl2 → CH3- CHCl-CH2Cl
propene propene dichloride
(1,2-dichloro propene)
CH2=CH2 + Br2 → CH2Br-CH2Br
ethene (1% solution) ethene dibromide
(colourless)
CH3-CH=CH2 + Br2 → CH3- CHBr-CH2Br
propene (reddish brown) propene dibromide
(colourless)
iii. Hydrohalogenation (Addition of alkyl halide/halogen acid)
(a) Symmetrical alkene (ethene)
CH2=CH2 + HX → CH3-CH2X
ethene ethyl halide
CH2=CH2 + HCl → CH3-CH2Cl
ethene ethyl chloride
CH2=CH2 + HBr → CH3-CH2Br
ethene ethyl bromide
CH2=CH2 + HI → CH3-CH2I
ethene ethyl iodide
(b) Unsymmetrical alkene (propene)
CH3-CH=CH2 + HX → CH3-CHX-CH3 + CH3-CH2-CH2X
propene iso-propyl halide n-propyl halide
(unsymmetrical) (major product) (minor product)
CH3-CH=CH2 + HBr → CH3-CHBr-CH3 + CH3-CH2-CH2Br

propene iso-propyl n-propyl bromide
(unsymmetrical) bromide
(major product) (minor product)
Markownikoff’s Rule
When an unsymmetrical addendum (HX) adds onto an
unsymmetrical alkene, two products are possible, but that product where
the negative part of the addendum adds onto the carbon with the least
number of hydrogen atoms is the major product.
(3) Formation of ozonide (Ozonolysis)
O
𝑐ℎ𝑙𝑜𝑟𝑜𝑓𝑜𝑟𝑚
CH2=CH2 + O3 → CH2 CH2
O O
ethene ethene ozonide
O
𝑍𝑛 𝑑𝑢𝑠𝑡
CH2 CH2 + H2O → 2HCHO + H2O2
O O
ethene ozonide methanal
(formaldehyde)
O
CH3-CH=CH2 + O3 → CH3-CH CH2
O O
propene propene ozonide
O
CH3-CH CH2 + H2O →𝑍𝑛 𝑑𝑢𝑠𝑡 CH3-CHO+ HCHO + H2O2
O O
propene ozonide ethanal methanal
(acetaldehyde) (formalde
hyde)

(4) Hydroxylation of alkene

When ethene is passed into cold dilute 1% KMnO4 solution, the violet
colour of KMnO4 solution is discharged and ethene glycol is formed.
CH2=CH2 + H2O + [O] 𝑐𝑜𝑙𝑑 𝑑𝑖𝑙𝑢𝑡𝑒 CH2OH-CH2OH
1%𝐾𝑀𝑛𝑂4
(violet)
ethene ethene glycol
(colourless)
CH3-CH=CH2 + H2O + [O] 𝑐𝑜𝑙𝑑 𝑑𝑖𝑙𝑢𝑡𝑒 CH3-CHOH-CH2OH
1%𝐾𝑀𝑛𝑂4
(violet)
propene propene glycol
(propane-1,2-diol)
(colourless)
(5) Polymerization
When ethene is passed over heated catalyst under high pressure,
polyethene is formed.
n(CH2=CH2) > 1000 𝑎𝑡𝑚 ( CH2-CH2 ) n
∆
ethene polyethene
(monomer) (polymer)
n(CH3-CH=CH2) > 1000 𝑎𝑡𝑚 (CH3- CH2 -CH2 ) n
∆
propene polypropene
(monomer) (polymer)
Uses of Ethenes
Ethene is used
- for ripening fruits
- industry in the manufacture of chemical solvent and
- in the manufacture of plastics
Preparations of alkynes
(1) Laboratory method to prepare ethyne or acetylene from coke (C)
(2) Dehydrohalogenation of alkene dihalide or alkylidene halide

(1) Laboratory method to prepare ethyne or acetylene from coke

When coke and calcium oxide are heated in an electric furnace,
calcium carbide is formed.
CaO + 3C 𝑒𝑙𝑒𝑐𝑡𝑟𝑖𝑐 CaC2 + CO
𝑓𝑢𝑟𝑛𝑎𝑐𝑒
coke calcium
carbide
CaC2 + 2H2O Ca(OH)2 + CH ≡ CH
ethyne or
acetylene
(2) Dehydrohalogenation of alkene dihalide or alkylidene halide
𝑒𝑡ℎ𝑎𝑛𝑜𝑙
R-CHX-CH2X + 2KOH ∆
R-C≡CH + 2KX + 2H2O
alkene dihalide alkyne
R-CH2-CHX2 + 2KOH ∆
alkylidene halide alkyne
CH2Br-CH2Br + 2KOH ∆
CH≡CH + 2KBr + 2H2O
ethene ethene
dibromide
CH3-CHBr2 + 2KOH ∆
CH≡CH + 2KBr + 2H2O
ethylidene ethyne
bromine
Chemical Properties of Alkynes
i. Hydrogenation or reduction (addition of hydrogen)
ii. Halogenation (addition of halogen)
iii. Hydrohalogenation (addition of hydrogen halide)
iv. Hydration
(2) Substitution
i. With sodium
ii. With ammoniacal copper (I) chloride solution
iii. With ammoniacal silver oxide solution


i. Hydrogenation or reduction
CH≡CH + H2 CH2=CH2 + H2 CH3-CH3
Pt or Pd Pt or Pd
ethyne ethene ethane
CH3- C≡CH + H2 CH3-CH=CH2 + H2 CH3-CH2-CH3
Pt or Pd Pt or Pd
propyne propene propane
ii. Halogenation (Cl2, Br2, I2)
(a) Addition of chlorine, Cl2
CH≡CH + Cl2 light CHCl=CHCl
𝑚𝑒𝑡𝑎𝑙𝑙𝑖𝑐
ethyne ℎ𝑎𝑙𝑖𝑑𝑒
ethyne dichloride
CHCl=CHCl + Cl2 light CHCl2 - CHCl2
𝑚𝑒𝑡𝑎𝑙𝑙𝑖𝑐
ethyne dichloride ℎ𝑎𝑙𝑖𝑑𝑒
ethyne tetrachloride
(b) Addition of bromine liquid, Br2 (l)
CH≡CH + Br2 (l) ethanol CHBr=CHBr
ethyne ethyne dibromide
CHBr=CHBr + Br2 (l) ethanol CHBr2 - CHBr2
ethyne dichloride ethyne tetrabromide
(c) Addition of aqueous bromine, Br2 (aq)
CH≡CH + Br2 (aq) CHBr=CHBr
ethyne ethyne dibromide
(d) Addition of iodine
CH≡CH + I2 ethanol CHI=CHI
ethyne ethyne di-iodide
iii. Hydrohalogenation
Addition of hydrogen halide or hydrogen acid (HCl, HBr, HI)
CH≡CH + HBr ethanol CH2=CHBr
ethyne vinyl bromide
symmetrical
CH2=CHBr + HBr ethanol CH3-CHBr2
vinyl bromide ethylidene bromide
unsymmetrical

iv. Hydration
When ethyne (acetylene) is passed into dilute sulphuric acid
containing mercury (II) sulphate at 600C, ethanol is formed.
CH≡CH + H2O 𝐻2 𝑆𝑂4 , 600 𝐶 [CH2=CHOH] CH3-CHO
𝐻𝑔++
ethyne vinyl alcohol ethanol
(unstable) (acetyldehyde)
(2) Substitution reactions
The hydrogen atom on a triple bonded carbon can be replaced by
metals such as Na, Cu and Ag.
i. With sodium (Na)
When acetylene gas is passed over heated sodium, the acetylenic
hydrogen atoms are substituted by sodium.
∆
CH≡CH + Na CH≡C-Na + 1
2
H2
ethyne monosodium acetylide
∆
CH≡C-Na + Na Na-C ≡ C-Na + 1
2
H2
monosodium disodium acetylide
acetylide
ii. With ammoniacal copper (I) chloride solution (Cu2Cl2)
When ethyne is passed into ammoniacal copper (I) chloride solution,
red precipitate of dicopper acetylide is formed.
2CH≡CH + Cu2Cl2 + 2NH3 2CH ≡ C-Cu ↓ + 2NH4Cl
acetylene monocopper (I)
acetylide
(red p.p.t)
2CH≡C-Cu + Cu2Cl2 + 2NH3 2Cu-C ≡ C-Cu ↓ + 2NH4Cl
monocopper dicopper (I)
acetylide acetylide
(red p.p.t)
2CH3-C≡CH + Cu2Cl2 + 2NH3 2CH3-C≡C-Cu ↓ + 2NH4Cl
methyl copper (I)
acetylene methyl acetylide
(propyne) (red p.p.t)

2CH3-CH2-C≡CH + Cu2Cl2 + 2NH3 2CH3-CH2-C≡C-Cu ↓ + 2NH4Cl

ethyl acetylene copper (I) ethyl
(1-butyne) acetylide
(red p.p.t)
CH3-C ≡ C-CH3 + Cu2Cl2 + NH3 no reaction
dimethyl
acetylene
(2-butyne)
iii. With ammoniacal silver oxide solution (Ag2O)
When ethyne is passed into ammoniacal solution of silver oxide,
white precipitate of disilver acetylide is formed.
2CH ≡ CH + Ag2O + NH3 2CH≡C-Ag↓ + NH4OH
acetylene monosilver
(ethyne) acetylide
(white p.p.t)
2CH≡C-Ag + Ag2O + NH3 2Ag-C≡C-Ag ↓ + NH4OH
monosilver disilver
acetylide acetylide
(white p.p.t)
2CH3-C≡CH + Ag2O + NH3 2CH3-C≡C-Ag ↓ + NH4OH
methyl silver methyl
acetylene acetylide
(propyne) (white p.p.t)
2CH3-CH2-C≡CH + Ag2O + NH3 2CH3-CH2-C≡C-Ag ↓ + NH4OH

ethyl acetylene copper (I) ethyl
(1-butyne) acetylide
(white p.p.t)
CH3-C ≡ C-CH3 + Ag2O + NH3 no reaction

dimethyl
acetylene
(2-butyne)

Uses of ethynes
- oxy-acetylene flame in welding and cutting steels.
- an important starting material in manufacture of plastic.
Preparations of Alcohols
(1) by the hydrolysis of alkyl halides
(2) by the hydrolysis of alkyl hydrogensulphate
(3) manufacture of ethanol from petroleum refinery products
(4) manufacture of ehanol by fermentation (fermentation method)
(1) By the hydrolysis of alkyl halides
Alkyl halides are heated under reflux with an aqueous solution of
sodium hydroxide (NaOH) or potassium hydroxide (KOH).
R-CH2X + NaOH reflux R-CH2OH + NaX

alkyl halide alkyl alcohol
CH3-CH2Cl + NaOH reflux CH3 -CH2OH + NaCl

ethyl chloride ethanol
(2) By the hydrolysis of alkyl hydrogensulphate

Alkyl hydrogensulphate is heated under reflux with water.
R-CH2-SO4H + H2O reflux R-CH2OH + H2SO4

alkyl alkyl alcohol
hydrogensulphate
CH3-CH2-SO4H + H2O reflux CH3-CH2OH + H2SO4

ethyl ethanol
hydrogensulphate

(3) Manufacture of ethanol from petroleum refinery products

When ethene is passed into sulphuric acid, ethyl hydrogensulphate
and diethyl sulphate are formed.
5200 𝐶,12 𝑎𝑡𝑚
hydrocarbon → alkanes + ethene
(very high (C5H12 to C9H20) (by product)
molecular weight)
CH2=CH2 + H2SO4 CH3-CH2SO4H
ethene ethyl hydrogensulphate
CH2=CH2 + CH3-CH2SO4H (CH3-CH2)2 SO4
ethene diethyl sulphate
Hydrolysis of ethyl hydrogensulphate and diethyl sulphate give
ethanol.
CH3-CH2SO4H + H2O CH3-CH2OH + H2SO4
ethyl ethanol
hydrogensulphate
(CH3-CH2)2 SO4 + 2H2O 2CH3-CH2OH + H2SO4
diethyl sulphate ethanol
Ethanol formed is fractionally distilled.
(4) Manufacture of ethanol by fermentation (fermentation method)
Potatoes, maize, rice and other starchy cereals contain starch is
pressure-cooked, cooled and then treated with freshly germinated barley
(which is called malt) for one hour at 600C.
The enzyme diastase in malt breaks down the starch into sugar called
maltose.
𝑛 𝑑𝑖𝑎𝑠𝑡𝑎𝑠𝑒 𝑛
(C6H10O5)n + H2O C12H22O11
2 2
starch maltose
Yeast (maltase) is added to the maltose at room temperature and
maltose decomposes into glucose.
.
𝑦𝑒𝑎𝑠𝑡
C12H22O11 + H2O (𝑚𝑎𝑙𝑡𝑎𝑠𝑒)
2C6H12O6
maltose glucose
Yeast (zymase) is added to the glucose at room temperature and
glucose decomposes into ethanol.

C6H12O6 (𝑧𝑦𝑚𝑎𝑠𝑒) 2CH3-CH2OH + 2CO2
glucose ethanol
The product contains about 11% ethanol.
It is fractionally distilled to yield the rectified spirit (about 95%
ethanol).
Physical properties of Alcohols
C1 to C4 = mobile liquids
C5 to C11 = oily liquids
C12 and above = usually solids
Methanol and ethanol are miscible with water in any proportion.
Methanol is the most toxic.
Chemical Properties of Alcohols
(1) reaction with metallic sodium
(2) reaction with phosphorus (V) chloride (PCl5)
(3) reaction with sulphuric acid
(4) formation of esters (esterification)
i. inorganic ester
ii. organic ester
(5) oxidation of alcohols
i. dehydrogenation with copper
ii. oxidation with acidified K2Cr2O7
(1) Reaction with metallic sodium (Na)
R-CH2OH + Na R-CH2ONa + 1
H2
2
alcohol sodium alkoxide
CH3-CH2OH + Na CH3-CH2ONa + 1
H2
2
ethanol sodium ethoxide
(2) Reaction with phosphorus (V) chloride (PCl5)
R-CH2OH + PCl5 𝑎𝑡 𝑟𝑜𝑜𝑚 R-CH2Cl + POCl3 + HCl
𝑡𝑒𝑚𝑝𝑒𝑟𝑎𝑡𝑢𝑟𝑒
alcohol alkyl chloride
CH3-CH2OH + PCl5 𝑎𝑡 𝑟𝑜𝑜𝑚 CH3-CH2Cl + POCl3 + HCl

ethanol ethyl chloride

(3) Reaction with sulphuric acid (H2SO4)

When ethanol is heated with an excess of concentrated sulphuric acid
at 1600C, ethene is the product.
CH3-CH2OH 𝐻2 𝑆𝑂4 (𝑐𝑜𝑛𝑐)1600 𝐶 CH2=CH2 + H2O
ethanol ethene
When ethanol is heated a smaller proportion of concentrated sulphuric
acid at 1400C, diethyl ether is formed.
CH3-CH2OH + H2SO4 1000 𝐶 CH3-CH2SO4H + H2O
sulphate
CH3-CH2OH + CH3-CH2SO4H 1400 𝐶 CH3-CH2-O-CH2-CH3 + H2SO4
ethanol diethyl ether
R-O-R = ether, R-COO-R = ester

(4) Formation of ester (esterification)
i. Inorganic ester
When alcohols are reacted with inorganic acid (HSO, HI, HBr, HCl)
inorganic esters are formed.
CH3-CH2OH + H2SO4 CH3-CH2SO4H + H2O
sulphate
(inorganic ester)
CH3-CH2OH + HI CH3-CH2I + H2O
ethanol ethyl iodide
(inorganic ester)
CH3-CH2OH + HCl ZnCl2
CH3-CH2Cl + H2O
ethanol ethyl chloride
(inorganic ester)
ii. Organic ester
When ethanoic acid (acetic acid) reacts with ethanol in the presence
of small amount of concentrated sulphuric acid, organic ester (ethyl
ethanoate) is formed.
An ester has a pleasant fruit odour.

𝐻2 𝑆𝑂4 (𝑐𝑜𝑛𝑐)
CH3-COOH + CH3-CH2OH CH3-COO-CH2-CH3 + H2O
𝐻+
ethanoic ethanol ethyl ethanoate
acid (ethyl acetate)
(organic ester)
(5) Oxidation of alcohols

i. Dehydrogenation (with copper)
When ethanol vapour is passed over freshly over reduced copper
heated 3000C, removal of hydrogen occurs with formation of ethanol or
acetaldehyde.
CH3-CH2OH 𝐶𝑢, 3000 𝐶 CH3-CHO + H2
ethanol ethanal
(vapour)
CH2-CH2-CH2OH 𝐶𝑢, 3000 𝐶 CH3-CH2-CHO + H2
n-propanol propanal
(vapour)
ii. Oxidation with acidified K2Cr2O7
When primary alcohol is oxidized, the first product will be an
aldehyde which go on further oxidation. The product will be the acids
containing the same number of carbon atoms.
CH3-CH2OH + [O] 𝐾2 𝐶𝑟2 𝑂7 CH3-CHO + H2O
𝐻2 𝑆𝑂4 (𝑑𝑖𝑙)
ethanol ethanal
CH3CHO + [O] 𝐾2 𝐶𝑟2 𝑂7 CH3COOH
ethanal ethanoic acid

Practice Questions
1. Give the IUPAC names for the following compounds.
(a) CH3
CH3-CH-CH2-CH3
(b) CH3
CH3-C-CH2-CH3
CH3
(c) CH3
CH3-C - CH-CH3
CH3 CH3
(d) CH3
CH3-CH-CH2-CH2-CH3
(e) CH3
CH3-C-CH2-CH2-CH3
CH3
(f) CH3
CH3-C - CH-CH2-CH3
CH3 CH3
(g) CH3 CH3
CH3-CH-CH-CH-CH3
CH3
(h) CH3
CH3-CH-CH-CH2-CH3
CH2-CH3
(i) CH3
CH3- C -CH2-CH2-CH3
CH3
(j) CH3
CH3 - C - CH-CH2-CH2-CH3
CH3 CH3

(k) CH3 CH3

CH3-CH-CH2-CH2-C-CH3
CH3
(l) CH3
CH3-C - CH-CH2-CH2-CH3
CH3 CH2-CH3
(m) CH3
CH3-C - CH-CH2-CH2-CH2-CH3
CH3 CH2-CH3
(n) CH3
CH3-CH2-CH-CH2-CH2-CH-CH2-CH3
CH2-CH3
(o) CH3
CH3-CH2-C-CH2-CH3
CH2-CH3
(p) CH3
CH3-CH-CH2-CH2-CH2-CH3
(q) CH3
CH3-CH2-CH-CH2-CH2-CH3
(r) CH3
CH3-CH-CH-CH2-CH2-CH3
CH3
(s) CH3 CH2-CH3
CH3-CH-CH2-CH-CH2-CH3
(t) CH3
CH3-CH-CH-CH2-CH2-CH3
CH2-CH3
(u) CH3 CH2-CH3
CH3-CH-CH2-CH2-CH-CH3
(v) CH3
CH3-CH2-CH-CH-CH2-CH3
CH2-CH3

(w) CH3
CH3 - C - CH-CH2-CH-CH3
CH3 CH3
(x) CH3
CH3-C-H
CH3
(y) CH3 CH3
CH - CH
CH3 CH3
(z) CH3
CH3-C-CH3
CH2-CH3
(aa) CH3
CH3 - C - CH - CH2-CH2-CH-CH3
CH3 CH2-CH3
(bb) CH3
CH3-C - CH-CH2-CH2-CH3
CH3 CH3
(cc) CH3 CH3
CH3-C - CH2-CH-CH2-CH3
CH2-CH3
(dd) CH2-CH3
CH3-CH -C-CH2-CH2-CH3
CH3 CH2-CH3
(ee) CH2-CH3
CH3-CH -C-CH2-CH2-CH3
CH3-CH2 CH3
(ff) CH3-CH2 CH3
CH3-C - C-CH2-CH2-CH3
CH3-CH2 CH2-CH3

(gg) CH3CH2-CH2-CH3
CH-CH-CH2-CH3
CH-CH3
CH3
(hh) CH3-CH2-CH2
CH2-CH2
CH2-CH2
CH2-CH2
CH3
(ii) CH3-CH2-CH2
CH=CH2
(jj) CH3
CH3-CH-CH=CH2
(kk) CH3
CH3-C=CH-CH3
(ll) CH2-CH3
CH3-CH-CH-CH=CH2
(mm) CH2-CH3
CH3-CH-CH-CH=CH2
CH3
(nn) CH3
CH3-C-CH=CH2
CH3
(oo) CH3
CH3-C - C=CH2
CH3 CH3
(pp) CH3
CH3-CH2-CH2-CH=CH2

(qq) CH3
CH3-CH-CH=CH2-CH3
(rr) CH3
CH3-C-CH2-CH2-CH=CH2
CH3
(ss) CH3
CH3 - C - CH-CH=CH-CH3
CH3 CH3
(tt) CH3
CH3 - C - CH-CH2-CH=CH2
CH3 CH2-CH3
(uu) CH3
CH3-C-CH=CH-CH3
CH3
(vv) CH3
CH3 - C - C=CH-CH3
CH3 CH3
(ww) CH3 CH3
CH2=C-CH-CH-CH3
CH3
(xx) CH3
CH3-CH2-C-CH=CH2
CH2-CH3
(yy) CH3 CH2-CH3
CH3-CH-CH=C-CH2-CH3
(zz) CH3
CH2=CH-CH-CH2 -C-CH3
CH2-CH3 CH3

(aaa) CH3
CH3-C-H
CH=CH2
(bbb) CH3-CH2 CH3
CH2=CH - C - CH - CH-CH2 - CH-CH3
CH2-CH3 CH2-CH3 CH3
(ccc) CH3-CH2-CH-CH2-CH2-CH3
CH=CH2
(ddd) CH3
CH3-CH2-C = C
CH3 CH2-CH2-CH3
(eee) CH3-CH2-CH2
CH2-C ≡ CH
(fff) CH3
CH3-CH2-CH2-C≡CH
(ggg) CH3
CH3-CH-C≡C-CH3
(hhh) CH3
CH3-C-CH2-C≡CH
CH3
(iii) CH3 CH3
CH3 - C - CH-C≡CH
CH3
(jjj) CH3
CH3-CH-CH-CH2-C≡CH
CH2-CH3

(kkk) CH3
CH3 - C - CH-CH2-C≡CH
CH3 CH2-CH3
(lll) CH3
CH3-CH2-C-C≡CH
CH2-CH3
(mmm) CH3 CH2-CH3
CH3-C - C- C ≡ CH
CH3 CH2-CH3
(ooo) CH3
CH3-C-CH-C ≡ CH
CH3
(ppp) CH3
CH3-CH-C ≡C-C-CH3
CH3 CH3
(qqq) CH3-CH2-CH2-CH2OH
(rrr) CH3
CH3-CH-CH2OH
(sss) CH3
CH3-CH2-CHOH
(ttt) CH3
CH3-C-CH3
OH
(uuu) CH3
CH3-CH-CH2-CH2OH
(vvv) CH3
CH3-CH2-CH-CHOH-CH3

(www) CH3
CH3-C-CH2-CH2-CHOH-CH3
CH2-CH3
(xxx) CH3
CH3-CH-CHOH-CH2-CH3
(yyy) CH3
CH3-CH2-C-CH2-CH2-CH2OH
CH2-CH3
(zzz) CH3-CH2-CH2-CHOH-CH2OH
(aaaa) CH3 CH3
CH3-C - CH-CHOH-CH2OH
CH3
(bbbb) CH3-CH2
CH3-CH2-C - CH-CH2-CH2OH
CH3 CH3
(cccc) CH3
CH3-C-CHOH-CH2-CH3
CH3
2. Draw the structural formulae of the following compounds.
(a) n-butane
(b) iso-butane
(c) neo-pentane
(d) 2-methyl butane
(e) 2-methyl pentane
(f) 3-methyl pentane
(g) 2-methyl hexane
(h) 3-methyl hexane
(i) 2,2-dimethyl butane
(j) 2,2-diethyl butane
(k) 2,2-dimethyl pentane

(l) 2,3-dimethyl pentane

(m) 2,2-dimethyl hexane
(n) 2,5-dimethyl heptane
(o) 2,2,3-trimethyl butane
(p) 2,2,3-trimethyl pentane
(q) 2,3,4-trimethyl pentane
(r) 2,2,3-trimethyl hexane
(s) 2,2,5-trimethyl hexane
(t) 2,2,3-trimethyl heptane
(u) 4,4,5-trimethyl nonane
(v) 3-ethyl 2-methyl pentane
(w) 3-ethyl 2-methyl hexane
(x) 3-ethyl 2-methyl heptane
(y) 3-ethyl 6-methyl octane
(z) 3-ethyl 3-methyl pentane
(aa) 4-ethyl 2-methyl hexane
(bb) 3-ethyl 2-methyl hexane
(cc) 3-ethyl 4-methyl hexane
(dd) 3-ethyl 2,2-dimethyl hexane
(ee) 3-ethyl 2,2-dimethyl heptane
(ff) 4-ethyl 2,2-dimethyl heptane
(gg) 3-ethyl 3-methyl butane
(hh) 1-butylene
(ii) 2-butylene
(jj) iso-butylene
(kk) s-dimethyl ethylene
(ll) uns-dimethyl ethylene
(mm) 3-methyl 1-butene
(nn) 4-methyl 1-pentene
(oo) 4-methyl 2-pentene
(pp) 3-methyl 1-butene
(qq) 2-methyl 2-butene
(rr) 3,3-dimethyl 1-butene
(ss) 5,5-dimethyl 1-hexene

(tt) 4,4-dimethyl 1-pentene

(uu) 4,4-dimethyl 2-pentene
(vv) 4,4-dimethyl 3-heptene
(ww) 3,4-dimethyl 1-pentene
(xx) 2,4-dimethyl 1-butene
(yy) 2,3,4-trimethyl 2-hexene
(zz) 5,6,6-trimethyl 3-heptene
(aaa) 2,3,4-trimethyl 1-pentene
(bbb) 4,5,5-trimethyl 2-hexene
(ccc) 2,3,3-trimethyl 1-butene
(ddd) 3-ethyl 3-methyl 1-pentene
(eee) 3-ethyl 4-methyl 1-pentene
(fff) 4-ethyl 5-methyl 1-heptene
(ggg) 3-methyl 4-ethyl 2-octene
(hhh) 3-methyl 4-ethyl 1-hexene
(iii) 2-ethyl 5-methyl 1-hexene
(jjj) 2-methyl 4-ethyl 3-hexene
(kkk) 5-ethyl 3,4-dimethyl 2-heptene
(lll) 3-ethyl 5,5-dimethyl 1-hexene
(mmm) 4-ethyl 5,5-methyl 1-hexene
(nnn) methyl acetylene
(ooo) ethyl acetylene
(ppp) dimethyl acetylene
(qqq) n-propyl acetylene
(rrr) iso-propyl acetylene
(sss) methyl ethyl acetylene
(ttt) 1-hexyne
(uuu) 3-methyl 1-butyne
(vvv) 4-methyl 1-pentyne
(www) 4-methyl 2-pentyne
(xxx) 4-ethyl 5-methyl 1-hexyne
(yyy) 4-ethyl 5-methyl 1-heptyne
(zzz) 3-ethyl 3-methyl 1-pentyne
(aaaa) 3-ethyl 4-methyl 1-propyne

(bbbb) 5-ethyl 2-methyl 3-heptyne

(cccc) 4-ethyl 5,5-dimethyl 1-hexyne
(dddd) 5-ethyl 4,6-dimethyl 2-heptyne
(eeee) 4,5-dimethyl 2-heptyne
(ffff) 3,4,4-trimethyl 1-pentyne
(gggg) 5,6,6-trimethyl 3-heptyne
(hhhh) 4,4-dimethyl 2-pentyne
(iiii) 3,4,5,5-tetramethyl 1-hexyne
(jjjj) 1-propanol (propan-1-ol)
(kkkk) 2-propanol (propan-2-ol)
(llll) 1-butanol (butan-1-ol)
(mmmm) 2-methyl propanol
(nnnn) 2-butanol
(oooo) 2-methyl 2-propanol
(pppp) 4-methyl 1-pentanol
(qqqq) 3-methyl 2-pentanol
(rrrr) 5,5-dimethyl 1-heptanol
(ssss) 2-methyl 3-pentanol
(tttt) 4-ethyl 4-methyl 1-hexanol
(uuuu) 3-methyl butan-1-ol
(vvvv) 4,4-dimethyl pentan-2-ol
(wwww) 3,3,4-trimethyl hexan-1-ol
(xxxx) 4,5,5-trimethyl heptan-1-ol
(yyyy) pentan-1,2-diol
3. Complete the following reactions.
∆
(a) R-COONa + NaOH
∆
(b) CH3COONa + NaOH
∆
(c) CH3-CH2COONa + NaOH
∆
(d) C3H7-COONa + NaOH
(e) R-I + HI
(f) CH3-CH2I + HI
(g) CH3-CH2-CH2I + HI
(h) CH3I + H2
(i) CH3-CH2I + H2

(j) CH2=CH2 + H2 𝑁𝑖, 3000 𝐶
(k) CH3-CH=CH2 + H2 𝑁𝑖, 3000 𝐶

H2 SO4 (conc)
(l) CH3-CH2OH 1600 C
H2 SO4 (conc)
(m) CH3-CHOH-CH3 1600 C
Al2 O3
(n) CH3-CH2OH 3500 C
Al2 O3
(o) CH3-CH2-CH2OH 3500 C
(p) CH3-CH2Cl + KOH ∆
(q) CH3-CH2-CH2Cl + KOH ∆
𝑁𝑖, 3000 𝐶
(r) R-CH=CH2 + H2
𝑁𝑖, 3000 𝐶
(s) CH3-CH=CH2 + H2
(t) R-CH=CH2 + X2
(u) CH2=CH2 + Cl2
(v) CH3-CH=CH2 + Br2
(w) CH2=CH2 + HX
(x) CH2=CH2 + HCl
(y) CH2=CH2 + HBr
(z) CH3-CH=CH2 + HBr
(aa) CH2=CH2 + O3
𝐶𝐻𝐶𝑙3
(bb) CH3-CH=CH2 + O3
1%𝐾𝑀𝑛𝑂4
(cc) CH2=CH2 + H2O + [O]
1%𝐾𝑀𝑛𝑂4
(dd) CH3-CH=CH2+H2O + [O]
𝑒𝑙𝑒𝑐𝑡𝑟𝑖𝑐
(ee) CaO + C 𝑓𝑢𝑟𝑛𝑎𝑐𝑒
(ff) CaC2 + H2O
(gg) R-CHX-CH2X + KOH ∆
(hh) CH2Br-CH2Br + KOH ∆
(ii) CH3-CHBr + KOH ∆
(jj) CH≡CH + H2
(kk) CH3-C ≡ CH + H2
𝑙𝑖𝑔ℎ𝑡
(ll) CH ≡ CH + Cl2
(mm) CH ≡ CH + Br2(l)
(nn) CH ≡ CH + Br2(aq)
(oo) CH ≡ CH + I2
(pp) CH ≡ CH + HBr
(qq) CH3-C ≡ CH + HBr
(rr) CH ≡ CH + H2O 𝐻2 𝑆𝑂4 , 600 𝐶

𝐻𝑔++
(ss) CH ≡ CH + Na
(tt) CH ≡ CH + Cu2Cl2 + NH3
(uu) CH3-CH2-C ≡ CH + Cu2Cl2 + NH3
(vv) CH ≡ CH + Ag2O + NH3
(ww) CH3-CH2-C ≡ CH + Ag2O + NH3
(xx) CH3-CH2Cl + NaOH reflux
(yy) CH3-CH2-SO4H + H2O reflux
(zz) CH2=CH2 + H2SO4

(aaa) CH2=CH2 + CH3-CH2SO4H
(bbb) (CH3-CH2)2SO4 + H2O
(ccc) C6H12O6 𝑧𝑦𝑚𝑎𝑠𝑒
(ddd) CH3-CH2OH + Na
(eee) CH3-CH2OH + PCl5
(fff) CH3-CH2OH 𝐻2 𝑆𝑂4 (𝑐𝑜𝑛𝑐 )
1600 𝐶
(ggg) CH3-CH2OH + H2SO4 1000 𝐶
(hhh) CH3-CH2OH + CH3-CH2SO4H 1400 𝐶
(iii) CH3-CH2OH + H2SO4

(jjj) CH3-CH2OH + HBr
𝑍𝑛𝐶𝑙2
(kkk) CH3-CH2OH + HCl
(lll) CH3-COOH + CH3-CH2OH
𝐻+
(mmm) CH3-CH2OH 𝐶𝑢, 3000 𝐶
𝐾2 𝐶𝑟2 𝑂7
(ooo) CH3-CH2OH + [O] 𝐻2 𝑆𝑂4 (𝑑𝑖𝑙)
4. What happen when

(a) sodium ethanoate is heated with soda lime?
(b) sodium propanoate is heated with soda lime?
(c) ethyl iodide is tested with hydrogen iodide?
(d) n-propyl chloride is treated with hydrogen chloride?
(e) methyl iodide is reacted with hydrogen in the presence of Pt?
(f) iso-propyl bromide is reacted with hydrogen using Pt catalyst?
(g) methane is mixed with chlorine in diffused sunlight?
(h) ethanol is passed over alumina, Al2O3 heated at 3500C?
(i) passing iso-propyl alcohol over alumina, Al2O3 heated at 3500C?
(j) propan-1-ol is heated with concentrated sulphuric acid at 1600C?

(k) ethanol is heated with H2SO4 (conc) at 1600C?
(l) propan-1-ol is heated with H2SO4 (conc) at 1600C?
(m) propan-2-ol is heated with H2SO4 (conc) at 1600C?
(n) ethanol reacts with concentrated sulphuric acid at 1000C?
(o) 1-propanol reacts with concentrated sulphuric acid at 1000C?
(p) 2-propanol reacts with concentrated sulphuric acid at 1000C?
(q) ethyl chloride is heated with alcoholic potassium hydroxide?
(r) n-propyl chloride is heated with alcoholic KOH?
(s) iso-propyl chloride is heated with alcoholic potassium hydroxide
solution?
(t) ethene is passed into 1% bromine in CCl4?
(u) propene is passed into 1% bromine in CCl4?
(v) ethene reacts with hydrogen iodide?
(w) propene reacts with hydrogen chloride?
(x) hydrogen bromide is added to propene?
(y) ethene is passed into 1% KMnO4 solution?
(z) propene is passed into 1% KMnO4 solution?
(aa) ozonized oxygen is passed into ethene in chloroform and the product
is decomposed by water?
(bb) ethene ozonide is decomposed with water?
(cc) propene ozonide is decomposed with water?
(dd) calcium oxide reacts with coke?
(ee) calcium carbide is treated with water?
(ff) ethene dibromide is heated with alcoholic KOH?
(gg) ethlidene chloride is heated with alcoholic potassium hydroxide?
(hh) ethyne is reacted with excess hydrogen in the presenceof Pt of Pd?
(ii) ethyne reacts with chloride in sunlight?
(jj) ethyne reacts with liquid bromine in the absence of solvent?
(kk) ethyne reacts with aqueous bromine in the absence of solvent?
(ll) ethyne reacts with an excess of HBr in the presence of light and
metallic halide?
(mm) vinyl bromide reacts with hydrogen bromide?

(nn) ethyne is passed into dilute sulphuric acid containing mercury (II)
sulphate ar 600C?
(oo) ethyne is passed into ammoniacal copper (I) chloride solution?
(pp) methyl acetylene is passed into ammoniacal copper (I) chloride
solution?
(qq) ethyl acetylene is passed into ammoniacal solution of silver oxide?
(rr) ethyne is passed into ammoniacal solution of silver oxide?
(ss) methyl acetylene is passed into ammoniacal solution of silver oxide?
(tt) ethyl acetylene is passed into ammoniacal solution of silver oxide?
(uu) ethyl chloride is passed into reflux with an aqueous solution of
KOH?
(vv) ethyl hydrogen sulphate is passed into reflux with water?
(ww) maltose is treated with enzyme maltase?
(xx) glucose is treated with zymase which is present in yeast?
(yy) ethanol is passed over freshly reduced Cu at 3000C?
(zz) a piece of sodium is added to ethanol?
(aaa) Ethanol reacts with phosphorus (V) chloride?
(bbb) ethanol is heated with concentrated sulphuric acid at 1000C?
(ccc) ethanol is heated with small amount of sulphuric acid?
(ddd) ethyl hydrogensulphate is treated with ethanol at 1400C?
(eee) ethanol is heated with a mixture of potassium dichromate and dilute
sulphuric acid?
(fff) ethanol is treated with hydrogen chloride in the presence of zinc
chloride?
(ggg) the reaction of ethanol with ethanoic acid?
5. How would you prepare
(a) ethane from ethene?
(b) methane from methyl iodide?
(c) ethane from ethyl iodide?
(d) ethyl chloride from ethene?
(e) methane from sodium ethanoate?
(f) ethane from sodium propanoate?
(g) ethane from ethene?
(h) methanol from ethene?
(i) propene from iso-propyl chloride?

(j) ethanal from ethyne?
(k) ethyne from ethylidene chloride?
(l) ethyne from ethene di bromide?
(m) dicopper acetylide from acetylene?
(n) ethanol from ethyl chloride?
(o) ethanal (acetaldehyde) from ethanol?
(p) ethanoic acid from ethanol?
(q) dimethyl ether from ethanol?
(r) diethyl ether from ethanol?
(s) ethyl ethanoate (ethyl acetate) from ethanol?
(t) maltose from starch?
(u) glucose from maltose?
(v) ethanol from glucose?
(w) sodium ethoxide from ethanol?
6. Illustrate the following reactions (alkanes):
(a) soda lime reaction
(b) reduction of alkyl halide by hydrogen halide
(c) reduction of alkyl halide by hydrogen
(d) chlorination of methane
(e) combustion of propane
7. Illustrate the following reactions (alkenes):
(a) Dehydration of n-propyl alcohol
(b) Dehydrohalogenation of iso-propyl chloride
(c) Dehydrohalogenation of n-propyl chloride
(d) Halogenation of ethene
(e) Hydrogenation of propene
(f) Formation of ozonide (ozonolysis)
(g) Hydroxylation of propene
8. Illustrate the following reactions (alkynes):
(a) hydration
(b) hydrogenation
(c) halogenation

(d) hydrohalogenation
(e) formation of silver acetylide
(f) hydrohalogenation of alkyne
9. Illustrate the following reactions (alcohols):
(a) dehydrogenation of ethanol
(b) esterification (formation of ester)
(c) oxidation of alcohol
10. Answer the following questions.
(a) A gas X is obtained by heating a mixture of sodium ethanoate and
soda lime. What is gas X? Write down the equation.
(b) Gas X can be obtained by hydrogenation of alkyl halide using a
palladium catalyst. Name the alkyl halide. Write down the equation.
(c) A gas Y is obtained by heating a mixture of sodium propanoate and
soda lime. What is gas Y? Write down the equation.
(d) Gas Y can also be obtained by hydrogenation of alkyl halide using
a palladium catalyst. Name the alkyl halide. Write down the
equation.
(e) Gas Y can also be obtained by hydrogenation of an alkene using a
nickel catalyst at 3000C. Name the alkene. Write down the equation.
(f) A gas X is obtained by heating a mixture of Y and soda lime. Y may
be obtained from the reaction between NaOH and acetic acid. Write
down a balanced equation in symbols for the first reaction only and
name the compound X and Y.
Is gas X saturated or unsaturated hydrocarbon?
Does gas X undergo addition?
Write down the general formula.
(g) A gas Y is obtained by heating a mixture of ethanol and concentrated
sulphuric acid at 1600C. What is gas Y? Write down the chemical
equation.
(h) Gas X is obtained by passing the vapour of ethanol over alumina,
Al2O3, at 3500C. What is gas X? Write down the chemical equation.
(i) A gas G is obtained by heating the ethyl chloride with an alcoholic
potassium hydroxide on the water bath. What is gas G? Write down
the chemical reaction.
(j) A gas B is obtained by heating normal propyl bromide with an

alcoholic potassium hydroxide on the water bath. What is gas B?
Write down the chemical reaction.
(k) A gas A is obtained by heating a mixture of propanol and alumina,
Al2O3, at 3500C. What is gas A? Write down the chemical reaction.
(l) When the compound X undergoes ozonolysis, the final product is
methanol. What is compound X? Write down the relevant equation.
(m) When the compound Y undergoes ozonolysis, the final product is
ethanol. What is compound Y? Write down the relevant equation.
(n) A gas X is obtained by heating ethylidene chloride with alcoholic
potassium hydroxide. What is gas X? Write down the equation.
(o) A gas Y is obtained by heating ethene dichloride with alcoholic
potassium hydroxide. What is gas Y? Write down the equation.
(p) A gas B is obtained by heating propene dibromide with an alcoholic
potassium hydroxide solution. What is gas B? Write down the
chemical equation.
(q) When gas A is passed into dilute sulphuric acid containing mercury
(II) sulphate at 600C, the final product is ethanol. What is gas A?
Write down the equation.
(r) A gas G is obtained by heating the calcium carbide with water. What
is gas G? Write down the equation.
(s) When ethyl hydrogensulphate is reflux with aqueous solution of
sodium hydroxide, compound X is formed. What is compound X?
write down the reaction.
(t) Compound Y can be formed by the fermentation of glucose with
enzyme zymase. What is compound Y? Write down the equation.
(u) The compound X is obtained by passing ethene into cold dilute
potassium permanganate solution. What is compound X? Write
down the equation.
(v) When compound Z is treated with PCl5, ethyl chloride is obtained.
What is compound Z? write down the equation.
(w) When phosphorous (V) chloride reacts with ethnol at room
temperature. Gas B is liberated. What is the Gas B? Write down the
chemical equation.

(x) A compound X is obtained by the reaction of ethanol with HCl in

the presence of anhydrous zinc chloride. What is compound X?
Write down the equation?
(y) A compound B undergoes esterification with ethnoic acid and the
final product is ethyl acetate. What is compound B? Write down the
relevant equation.
(z) A compound X is formed by passing ethanol over freshly reduced
copper heated at 3000C. What is compound X? Write down the
equation.
(aa) A gas Z is liberated by adding a piece of sodium to ethanol at room
temperature. What is gas Z? Write down the equation.
11. How would you differentiate (distinguish) between:
(a) alkene and alkane (ethane and ethane; propane and propene; iso-
butane and iso-butene)
R-CH=CH2 + H2O + [O] 𝑐𝑜𝑙𝑑 𝑑𝑖𝑙𝑢𝑡𝑒 R-CHOH-CH2OH
alkene 1%𝐾𝑀𝑛𝑂4 (𝑣𝑖𝑜𝑙𝑒𝑡) alkene glycol
(colourless)
R-CH3-CH2 + H2O + [O] 𝑐𝑜𝑙𝑑 𝑑𝑖𝑙𝑢𝑡𝑒 No decolourization
alkane 1%𝐾𝑀𝑛𝑂4 (𝑣𝑖𝑜𝑙𝑒𝑡)
(b) alkene and alkyne [ethene (ethylene) and ethyne (acetylene),

propene and propyne]
R-C≡CH + Cu2Cl2 + 2NH3 2R-C≡C-Cu ↓ + 2NH4Cl
alkyl acetylene copper (I) alkyl
(propyne) acetylide
(red p.p.t)
R-CH=CH2 + Cu2Cl2 + NH3 no reaction

alkene (no p.p.t)
(c) alkane and alkyne [ethane and ethyne(acetylene), propane and
propyne, n-butane and 1-butyne]
R-C≡CH + Cu2Cl2 + 2NH3 2R-C≡C-Cu ↓ + 2NH4Cl
alkyl acetylene copper (I) alkyl
(propyne) acetylide
(red p.p.t)
R-CH2-CH3 + Cu2Cl2 + NH3 no reaction
alkane (no p.p.t)

(d) 1-butyne and 2-butyne (distinguishes between C4H6 isomers)

CH3-CH2-C≡CH + Cu2Cl2 + 2NH3 2CH3-CH2-C≡C-Cu ↓ + 2NH4Cl
ethyl acetylene copper (I) ethyl acetylide
(1-butyne) (red p.p.t)

dimethyl acetylene (no p.p.t)
(2-butyne)
Fig. Fractional distillation process in a refinery

Alkanes
Preparations of Alkanes
(1) Heating sodium salt of carboxylic acid with soda lime

R-COONa + NaOH CaO R-H + Na2CO3
sodium alkanoate alkane
(2) Reduction of alkyl halides

i. With hydrogen halide (Hydrohalogenation)
R-X + HX → R-H + X2
alkyl halide alkane
ii. With hydrogen using platinum(Pt) or palladium(Pd) catalyst
(Hydrogenation)
R-X + H2 → R-H + HX
alkyl halide alkane
iii. Reduction of alkene with hydrogen
(Hydrogenation)
R-CH=CH2 + H2 𝑁𝑖,3000𝐶 R-CH2-CH3
→
alkene alkane
Chemical Properties of Alkanes

∆
R-H + O2 → CO2 + H2O
alkane
(2) Chlorination of methane (Substitution reaction)

CH4 + Cl2 → CH3Cl → CH2Cl2 → CHCl3 → CCl4
methane methyl methylene chloroform carbon
chloride chloride tetrachloride
diffused sunlight

Alkenes
Preparations of Alkenes
(1) Dehydration of alcohol

Two stages
0𝐶
→
R-CH2-CH2SO4H + H2O
sulphate
→
R-CH=CH2 + H2SO4
alkene
One stage
0
alcohol 160 𝐶 alkene
ii. Passing alcohol vapour over alumina catalyst heated at 3500C
alcohol 𝟑𝟓𝟎𝟎 𝑪 alkene
ethanol
R-CH2-CH2X + KOH R-CH2=CH2 + KX + H2O
alkyl halide alkene
Chemical Properties of Alkenes

∆
R-CH=CH2 + O2 → CO2 + H2O
alkene
i. Hydrogenation (Addition of hydrogen)
R-CH=CH2 + H2 →𝑁𝑖,200−3000𝐶 R-CH2-CH3
alkene alkane
ii. Halogenation (Addition of halogen)
R-CH=CH2 + X2 → R-CHX-CH2X
alkene alkene dihalide

iii. Hydrohalogenation (Addition of alkyl halide or halogen acid)

(a) Symmetrical alkenes
CH2=CH2 HX → CH3-CH2X
ethene (symmetrical) ethyl halide
(b) Unsymmetrical alkenes
CH3-CH=CH2 + HX → CH3-CX-CH3 + CH3-CH2-CH2-X
propene iso-propyl halide n-propyl halide
(unsymmetrical) (major product) (minor product)
(3) Ozonolysis (Formation of ozonide)
O
CH2=CH2 + O3 → CH2 CH2
O O
ethene ethene ozonide
O
𝑍𝑛 𝑑𝑢𝑠𝑡
CH2 CH2 + H2O → 2HCHO + H2O2
O O
ethene ozonide methanal
(formaldehyde)
(4) Hydroxylation
R-CH=CH2 + H2O + [O] 𝑐𝑜𝑙𝑑 𝑑𝑖𝑙𝑢𝑡𝑒 R-CHOH-CH2OH
Alkene 1%𝐾𝑀𝑛𝑂4 alkene glycol
(violet) (colourless)
(5) Polymerization
n(CH2=CH2) > 1000 𝑎𝑡𝑚 ( CH2-CH2 ) n
ethene ∆ polyethene
(monomer) (polymer)
....................................................................................................................
Alkynes
Preparations of Alkynes
(1) Laboratory method to prepare ethyne or acetylene from coke
CaO + 3C 𝑒𝑙𝑒𝑐𝑡𝑟𝑖𝑐 CaC2 + CO
coke 𝑓𝑢𝑟𝑛𝑎𝑐𝑒 calcium
carbide
CaC2 + 2H2O Ca(OH)2 + CH ≡ CH
ethyne

(2) Dehydrohalogenation of alken dihalide or alkylidene halide

R-CHX-CH2X + 2KOH ∆
alkene dihalide alkyne
R-CH2-CHX2 + 2KOH ∆
alkylidene halide alkyne
Chemical Properties of Alkynes

v. Hydrogenation or reduction
CH ≡ CH + H2 CH2=CH2 + H2 CH3-CH3
ethyne Pt or Pd ethene Pt or Pd ethane
vi. Halogenation
CH ≡ CH + Cl2 𝑙𝑖𝑔ℎ𝑡 CHCl=CHCl
ethyne 𝑚𝑒𝑡𝑎𝑙𝑙𝑖𝑐 ℎ𝑎𝑙𝑖𝑑𝑒 ethyne dichloride
CHCl=CHCl + Cl2 𝑙𝑖𝑔ℎ𝑡 CHCl2 - CHCl2

ethyne dichloride 𝑚𝑒𝑡𝑎𝑙𝑙𝑖𝑐 ℎ𝑎𝑙𝑖𝑑𝑒 ethyne tetrachloride
Notes; Br(aq) has only one stage
vii. Hydrohalogenation
CH ≡ CH + HBr CH2=CHBr
ethyne vinyl bromide
(symmetrical)
CH2=CHBr + HBr CH3-CHBr2
vinyl bromide ethylidene bromide
(unsymmetrical)
viii. Hydration
CH≡CH + H2O 𝐻2 𝑆𝑂4 , 600 𝐶 CH2=CHOH CH3-CHO
𝐻𝑔++
ethyne vinyl alcohol ethanol
(unstable)
(2) Substitution reaction
i. sodium
∆
CH ≡ CH + Na CH ≡ C-Na + 1
2
H2
ethyne monosodium acetylide
∆
CH ≡ C-Na + Na Na-C ≡ C-Na + 1
2
H2
monosodium disodium acetylide
acetylide

ii. With ammoniacal copper (I) chloride solution

2CH ≡ CH + Cu2Cl2 + 2NH3 2CH≡C-Cu ↓ + 2NH4Cl
acetylene monocopper (I)
acetylide
(red p.p.t)
2CH ≡ C-Cu + Cu2Cl2 + 2NH3 2Cu-C ≡ C-Cu ↓ + 2NH4Cl

monocopper dicopper acetylide
acetylide (red p.p.t)
2CH3-C≡CH + Cu2Cl2 + 2NH3 2CH3-C≡C-Cu ↓ + 2NH4Cl

methyl acetylene copper (I) methyl
(propyne) acetylide
(red p.p.t)
2CH3-CH2-C≡CH + Cu2Cl2 + 2NH3 2CH3-CH2-C≡C-Cu ↓ + 2NH4Cl

ethyl acetylene copper (I) ethyl acetylide
(1-butyne) (red p.p.t)

(2-butyne)
iii. With ammoniacal silver oxide solution
2CH ≡ CH + Ag2O + NH3 2CH ≡ C-Ag↓ + NH4OH

acetylene monosilver acetylide
(ethyne) (white p.p.t)
2CH≡C-Ag + Ag2O + NH3 2Ag-C≡C-Ag ↓ + NH4OH

monosilver disilver acetylide
acetylide (white p.p.t)
2CH3-C ≡ CH + Ag2O + NH3 2CH3-C≡C-Ag ↓ + NH4OH

methyl acetylene silver methyl acetylide
(propyne) (white p.p.t)
2CH3-CH2-C≡CH + Ag2O + NH3 2CH3-CH2-C≡C-Ag ↓ + NH4OH

ethyl acetylene silver ethyl acetylide
(1-butyne) (white p.p.t)

CH3-C C-CH3 + Ag2O + NH3 no reaction

(2-butyne)
Special Notes for Naming Radicals
CH3-CH3 CH3-CH2Cl CH3-CHCl2

ethane ethyl chloride ethylidene chloride
CH2Cl-CH2Cl
ethene dichloride
.
CH3-CH2-CH3 CH3-CH2-CH2Cl CH3-CH2-CHCl2

propane n-propyl chloride n-propylidene chloride
CH3-CHCl-CH3 CH3-CCl2-CH3
iso-propyl chloride iso-propylidene chloride
CH3-CHCl-CH2Cl
propylene dichloride
CH2=CH2 CH2=CHCl
ethene ethenyl chloride
(vinyl chloride)
.
CH3-CH=CH2 CH3-CH=CHCl
propene n-propenyl chloride
(2-methyl vinyl chloride)
CH3-CHCl=CH2
iso-propenyl chloride
(1-methyl vinyl chloride)

Alcohols
Preparations of Alcohols
(1) Hydrolysis of alkyl halide
R-CH2X + NaOH reflux R-CH2OH + NaX
alkyl halide alkyl alcohol
(2) Hydrolysis of alkyl hydrogen sulphate

R-CH2-SO4H + H2O reflux R-CH2OH + H2SO4
alkyl alkyl alcohol
hydrogensulphate
(3) Manufacture of ethanol from petroleum refinery products
5200 𝐶,12 𝑎𝑡𝑚
hydrocarbon → alkanes + ethene
(very high (C5H12 to C9H20) (by product)
molecular weight)
CH2=CH2 + H2SO4 CH3-CH2SO4H
Ethene ethyl hydrogensulphate
CH2=CH2 + CH3-CH2SO4H (CH3-CH2)2 SO4
ethene diethyl sulphate
CH3-CH2SO4H + H2 O CH3-CH2OH + H2SO4
ethyl ethanol
hydrogensulphate
(CH3-CH2)2 SO4 + 2H2O 2CH3-CH2OH + H2SO4
diethyl sulphate ethanol
(4) Manufacture of ethanol by fermentation (fermentation method)

n diastase 𝑛
(C6H10O5)n + 2 H2O → 2
C12H22O11
starch maltose
+ H2O Yeast (maltase)
2CH3-CH2OH + 2CO2 yeast (zymase) C6H12O6

ethanol glucose
Chemical properties of Alcohols
(1) Reaction with metallic sodium
R-CH2OH + Na R-CH2ONa + 1
H2
alcohol sodium alkoxide 2

(2) Reaction with phosphorous (V) oxide, PCl5

R-CH2OH + PCl5 𝑎𝑡 𝑟𝑜𝑜𝑚 R-CH2Cl + POCl3 + HCl
alcohol alkyl chloride
(3) Reaction with sulphuric acid
0𝐶
→
R-CH2-CH2SO4H + H2O
sulphate
→
R-CH=CH2 + H2SO4
alkene
CH3-CH2OH + H2SO4 1000 𝐶 CH3-CH2SO4H + H2O

sulphate
CH3-CH2OH + CH3-CH2SO4H 1400 𝐶 CH3-CH2-O-CH2-CH3 + H2SO4
ethanol diethyl ether
(4) Formation of ester (esterification)

i. Inorganic ester
CH3-CH2OH + H2SO4 CH3-CH2SO4H + H2O
sulphate
(inorganic ester)
ii. Organic ester
CH3-COOH + CH3-CH2OH CH3-COO-CH2-CH3 + H2O
𝐻+
ethanoic acid ethanol ethyl ethanoate
(ethyl acetate)
(organic ester)
(5) Oxidation of alcohols
i. Dehydrogenation with copper at 3000C
CH3-CH2OH 𝐶𝑢, 3000 𝐶 CH3-CHO + H2
ethanol ethanal
(vapour)
ii. Oxidation with acidified K2Cr2O7
CH3-CH2OH + [O] 𝐾2 𝐶𝑟2 𝑂7 CH3-CHO + H2O
ethanol 𝐻2 𝑆𝑂4 (𝑑𝑖𝑙) ethanal
CH3CHO + [O] 𝐾2 𝐶𝑟2 𝑂7 CH3COOH
ethanal 𝐻2 𝑆𝑂4 (𝑑𝑖𝑙) ethanoic acid

Alkanes
I. Complete the following reactions and name the organic
compounds.
1. R-COONa + NaOH → 11. CH3Br + H2 →
2. CH3-COONa + NaOH → 12. CH3-CH2I + H2 →
3. CH3-CH2-COONa + NaOH → 13. CH3-CH2-CH2I + H2 →
4. C3H7-COONa + NaOH → 14. CH3-CHBr-CH3 + H2 →
5. RX + HX → 15. R-CH=CH2 + H2 →
6. CH3Cl + HCl → 16. CH2=CH2 + H2 →
7. CH3-CH2Cl + HCl → 17. CH3-CH=CH2 + H2 →
8. CH3-CH2-CH2Cl + HCl → 18. CH4 + O2 →
9. CH3-CHCl-CH3 + HCl → 19. CH3-CH3 + O2 →
10. RX + H2 → 20. CH4 + Cl2 →
II. What product would you expect when (OR) what happens when
1. sodium ethanoate is heated with soda lime?
2. sodium propanoate is heated with soda lime?
3. sodium butanoate is heated with soda lime?
4. methyl iodide is reduced with hydrogen iodide?
5. ethyl chloride reacts with hydrogen chloride?
6. n-propyl iodide is reduced with hydrogen iodide?
7. iso- propyl bromide reacts with hydrogen iodide?
8. methyl iodide is reduced with hydrogen?
9. ethyl chloride is reduced with hydrogen?
10. n-propyl iodide is reduced with hydrogen?
11. iso-propyl iodide is reduced with hydrogen?
12. ethene reacts with hydrogen in the presence of Ni at 3000C?
13. propene reacts with hydrogen using platinum or palladium catalyst?
14. methane is burnt in air?
15. methane is mixed with chlorine in diffused sunlight?
III. Write equation to illustrate each of the following reactions.
1. soda lime reaction
2. reduction of alkene
3. combustion of methane
Page-59
4. chlorination of methane
5. substitution reaction of methane
6. chlorination of methyl chloride
7. chlorination of methylene chloride
8. chlorination of chloroform
IV. How would you prepare
1. methane from sodium ethanoate?
2. ethane from sodium propanoate?
3. propane from sodium butanoate?
4. methane from methyl chloride?
5. ethane from ethyl bromide?
6. propane from n-propyl chloride?
7. propane from iso-propyl iodide?
8. ethane from ethene?
9. propane from propene?
10. carbon tetrachloride from methane?
V. Answer the followings.
1. A gas A is obtained by heating a mixture of sodium ethanoate and soda
lime. What is gas A? Write down the equation.
Gas A can also be obtained by hydrogenation of an alkyl halide using
a palladium catalyst. Name the alkyl halide. Write down the equation.
Is gas is saturated or unsaturated hydrocarbon?
2. A gas B is obtained by heating a mixture of sodium propanoate and
soda lime. What is gasB? Write down the equation.
3. A gas Y can be obtained by hydrogenation of methyl chloride. What is
gas Y? Write down the equation.
4. A gas X can be obtained by hydrogenation of ethyl bromide. What is
gas X? Write down the equation.
5. A gas A can be obtained by hydrogenation of n-propyl iodide. What is
gas A? Write down the equation.
6. A gas A can be obtained by hydrogenation of iso-propyl chloride. What
is gas A? Write down the equation.
7. A gas C can be formed by hydrogenation of ethene using a nickel
catalyst at 3000C. Name the gas C. Write down the equation.
Page-60
8. A gas Y can be formed by hydrogenation of propene using platinum or

palladium catalyst. Name the gas Y. Write down the equation.
9. A gas A can be obtained by hydrogenation of 1-butene using a nickel
catalyst at 3000C. Name the gas A. Write down the equation.
10. A gas B can be obtained by hydrogenation of 2-butene using a nickel
catalyst at 3000C. Name the gas B. Write down the equation.
11. A gas X is obtained by heating a mixture of Y and sodalime. Y may be
obtained for the first reaction, NaOH and acetic acid. Write down a
balanced equation in symbols for the first reaction ONLY, and name
the compound X and Y.
……………………………………………………………………………..
Alkenes
I. Complete the following reactions and name the organic compounds.

𝐻2𝑆𝑂4 (𝑐𝑜𝑛𝑐 ),1600𝐶
1. R-CH2-CH2OH →
2. CH3-CH2OH →
3. CH3-CH2-CH2OH →
4. CH3-CHOH-CH3 →
1000𝐶
5. CH3-CH2OH + H2SO4 (conc) →
1000𝐶
6. CH3-CH2-CH2OH + H2SO4 (conc) →
1600𝐶
7. CH3-CH2-CH2SO4H →
1600𝐶
8. CH3-CH2-CH2-SO4H →
𝐴𝑙2 𝑂3 ,3500𝐶
9. CH3-CH2OH →
𝐴𝑙2 𝑂3 ,3500𝐶
𝐴𝑙2 𝑂3 ,3500𝐶
11. CH3-CHOH-CH3 →
12. R-CH2X + KOH →
13. CH3-CH2Cl + KOH →
14. CH3-CH2-CH2Cl + KOH →
15. CH3-CHCl-CH3 + KOH →
16. CH2=CH2 + O2 →
Page-61
17. CH3-CH=CH2 + O2 →
18. CH2=CH2 + H2 →
19. CH3-CH=CH2 + H2 →
20. CH2=CH2 + Cl2 →
21. CH2=CH2 + Br2 →
22. CH2=CH2 + HX →
23. CH2=CH2 + HCl →
24. CH3-CH=CH2 + HX →
25. R-CH=CH2 + HCl →
26. R-CH=CH2 + HBr →
27. CH3-CH=CH2 + HBr →
28. CH3-CH=CH2 + HCl →
29. CH2=CH2 + O3 →
30. CH3-CH=CH2 + O3 →
𝑐𝑜𝑙𝑑 𝑑𝑖𝑙 𝐾𝑀𝑛𝑂4
31. CH2=CH2 + H2O + [O] →
(𝑣𝑖𝑜𝑙𝑒𝑡)
𝑐𝑜𝑙𝑑 𝑑𝑖𝑙 𝐾𝑀𝑛𝑂4
32. CH3-CH=CH2 + H2O + [O] →
(𝑣𝑖𝑜𝑙𝑒𝑡)
33. CH2=CH2 →
34. CH3-CH=CH2 →
II. What product would you expect when (OR) what happens when
1. ethyl alcohol (ethanol) is heated with concentrated sulphuric acid at
1600C?
2. propan-1-ol (n-propyl alcohol) is heated with H2SO4 (conc) at 1600C?
3. propan-2-ol (iso-propyl alcohol) is heated with H2SO4 (conc) at 1600C?
4. ethanol is passed over alumina heated at 3500C?
5. propan-1-ol is passed over alumina heated at 3500C?
6. propan-2-ol is passed over alumina heated at 3500C?
7. The vapour of propanol is passed over alumina heat at 3500C.
8. ethyl chloride is heated with an alcoholic potassium hydroxide solution
on a water bath?
9. n-propyl chloride is heated with an alcoholic potassium hydroxide
solution on a water bath?
10. iso-propyl chloride is heated with an alcoholic potassium hydroxide
solution on a water bath?
Page-62
11. An alkyl halide is heated with alcoholic potassium hydroxide solution

on a water bath?
12. Ethene is passed into aqueous bromine in CCl4?
13. propene is passed into liquid bromine in CCl4?
14. Ethene is passed into cold dilute 1% potassium permanganate solution?
15. Propene is passed into cold dilute potassium permanganate solution?
16. Ozonide oxygen is passed into a solution of ethene in chloroform and
the product formed is decomposed by water?
17. Ozonide oxygen is passed into a solution of propene in chloroform and
the product formed is decomposed by water?
18. Propene reacts with hydrogen bromide?
19. Propene reacts with hydrochloric acid?
20. Iso-butene would react with HBr?
21. Ethene polymerizes to a polymer?
III. Write equations to illustrate each of the following reactions.
1. Dehydration
2. Dehydration of ethanol
3. Dehydration of n-propyl alcohol
4. Dehydration of iso-propyl alcohol
5. Dehydrohalogenation
6. Dehydrohalogenation of alkyl halide
7. Dehydrohalogenation of ethyl chloride
8. Dehydrohalogenation of n-propyl chloride
9. Dehydrohalogenation of iso-propyl chloride
10. Hydrogenation
11. Hydrogenation of alkene
12. Hydrogenation of ethene
13. Hydrogenation of propene
14. Hydrogenation of 1-butene
15. Hydrogenation of 2-butene
16. Halogenation of ethene
17. Chlorination of ethene
18. Bromination of thene
19. Hydrohalogenation
Page-63
20. Hydrohalogenation of alkene

21. Hydrohalogenation of ethene
22. Hydrohalogenation of propylene
23. An addition reaction of alkene to illustrate Markownikoff’s rule
24. An addition of hydrogen chloride to propylene
25. An addition of hydrogen bromide to propene
26. Ozonolysis
27. Ozonolysis of ethene
28. Ozonolysis of propene
29. Formation of ozonide
30. Hydroxylation
31. Hydroxylation of ethene
32. Hydroxylation of propene
33. Addition reation of ethene
34. Polymerization of ethene
35. Polymerization of propene
IV. How would you prepare (obtain)
1. Alkene from alcohol?
2. Ethene (ethylene) from ethanol (ethyl alcohol)?
3. Propene (propylene) from n-propyl alcohol (propan-1-ol)?
4. Propene (propylene) from iso-propyl alcohol (propan-2-0l)?
5. Alkene from alkyl halide?
6. Ethene from ethyl chloride?
7. Propene from n-propyl chloride?
8. Propene from iso-propyl chloride?
9. Ethene from ethyl bromide?
10. Propene from n-propyl bromide?
11. Propene from iso-propyl bromide?
12. Propane from propylene (propene)?
13. Methanal from ethene (ethylene)?
14. Ethene ozonide from ethene?
15. Ethanal from propene?
16. ethene glycol from ethene?
17. Propene glycol from propene?
Page-64
V. Answer the followings.

1. A gas G is obtained by passing the vapour of ethanol over alumina at
3500C. What is gas G? Write down the chemical equation.
Gas G can also be produced by heating an alkyl halide with alcoholic
potassium hydroxide. Name the alkyl halide. Write down the equation.
Is the gas G saturated or unsaturated hydrocarbon? Give a chemical
equation to support your answer.
2. A compound X is obtained by heating ethanol with concentrated
sulphuric acid at 1600C. What is compound X? Write down the
chemical equation.
3. A compound X is obtained by heating 1-propanol with concentrated
chemical equation.
4. A compound X is obtained by heating 2-propanol with concentrated
chemical equation.
5. A gas B is obtained by heating a mixture of propanol and alumina at
3500C. What is gas B? Write down the chemical equation.
6. A gas X is obtained by heating ethyl chloride with alcoholic potassium
hydroxide on a water bath. What is gas X? Write down the chemical
equation.
7. A gas X is obtained by heating n-propyl bromide with alcoholic
potassium hydroxide on a water bath. What is gas X? Write down the
chemical equation.
……………………………………………………………………………
Alkynes
I. Complete the following compounds and name the organic
compounds.
1. C + CaO →
2. CaC2 + H2O →
3. CH2Br-CH2Br + KOH →
4. CH ≡ CH + O2 →
5. CH ≡ CH + H2 →
Page-65
6. CH2=CH2 + H2 →
7. CH3-C≡CH + H2 →
8. CH3-CH=CH2 + H2 →
9. CH≡CH + Cl2 →
10. CH≡CH + Br2 (l) →
11. CH≡CH + Br2 (aq) →
12. CH≡CH + I2 (l) →
13. CH≡CH + HCl →
14. CH2=CHCl + HCl →
15. CH≡CH + H 2O →
16. CH≡CH + Na →
17. CH≡CNa + Na →
18. CH3-CH2-C≡CH + Na →
19. CH≡CH + Cu2Cl2 + NH3 →
20. CH3-C≡CH + Cu2Cl2 + NH3 →
21. CH≡CCu + Cu2Cl2 + NH3 →
22. CH3-CH2-C≡CH + Cu2Cl2 + NH3 →
23. CH≡CH + Ag2O + NH3 →
24. CH3-C≡CH + Ag2O + NH3 →
25. CH≡CCu + Ag2O + NH3 →
26. CH3-CH2-C≡CH + Ag2O + NH3 →
II. What product would you expect when (OR) what happens when:
1. calcium oxide is heated with coke in an electric furnace?
2. calcium carbide is treated with water?
3. ethene dibromide is heated with an alcoholic solution of KOH?
4. 1,2-dibromo propane is heated with alcoholic potassium hydroxide?
5. ethen dichloride is heated with an alcoholic solution of KOH?
6. ethylidene chloride is heated with an alcoholic solution of potassium
hydroxide?
7. ethylidene bromide is heated with an alcoholic solution of potassium
hydroxide?
8. ethyne reacts with an excess of hydrogen in the presence of Pt or Pd?
9. propyne reacts with an excess of hydrogen in the presence of Pt or
Pd?
Page-66
10. ethyne react with cholrine in the dark by the presence of catalyst?
11. acetylene reacts with liquid bromine in the absence of solvent?
12. acetylene is passed into dilute sulphuric acid containing mercury (II)
sulphate at 600C?
13. ethyne reacts with hydrogen bromide?
14. 1-butyne reacts with an excess of hydrogen bromide?
15. acetylene (ethyne) is passed over heated sodium?
16. methyl acetylene (propyne) is passed over heated sodium?
17. ethyl acetylene (1-butyne) is passed over heated sodium?
18. dimethyl acetylene (2-butyne) is passed over heated sodium?
19. acetylene (ethyne) is passed into an ammonical solution of Cu2Cl2?
20. methyl acetylene is passed into an ammonical solution of copper (I)
chloride?
21. ethyl acetylene is passed into an ammonical solution of Cu2Cl2?
22. dimethyl acetylene is passed into an ammonical solution of Cu2Cl2?
23. acetylene is passed into an ammonical solution of silver oxide?
24. methyl acetylene is passed into an ammonical solution of Ag2O?
25. ethyl acetylene is passed into an ammonical solution of Ag2O?
26. dimethyl acetylene is passed into an ammonical solution of silver
oxide?
III. Write to illustrate each of the following reactions.

1. dehydrohalogenation of ethene dibromide
2. dehydrohalogenation of ethene dichloride
3. dehydrohalogenation of ethylidene bromide
4. dehydrohalogenation of ethylidene chloride
5. hydrogenation of ethyne
6. hydrogenation of propyne
7. chlorination of ethyne
8. bromination of ethyne
9. hydrohalogenation of ethyne
10. hydration of ethyne
11. hydration of propyne (methyl acetylene)
12. substitution reaction of alkyne
13. substitution reaction of acetylene
Page-67
14. substitution reaction of methyl acetylene

15. substitution reaction of ethyl acetylene
IV. How would you prepare (obtain)
1. ethyne (acetylene) from coke (carbon)?
2. ethyne (acetylene) from calcium carbide?
3. ethyne from ethene dibromide?
4. ethyne from ethene dichloride?
5. ethyne from ethylidene bromide?
6. ethyne from ethylidene chloride?
7. ethane from ethyne?
8. propane from propyne?
9. ethylidene bromide from ethyne?
10. ethyne dibromide from ethyne?
11. ethyne tetrabromide from ethyne?
12. ethanal from ethyne?
13. sodium methyl acetylide from propyne?
14. sodium ethyl acetylide from 1-bytyne?
15. dicopper acetylide from acetylene?
16. monocopper methyl acetylide from propyne?
17. monocopper ethyl acetylide from 1-butyne?
18. monosilver acetylide from ethyne?
19. disilver acetylide from ethyne?
20. monosilver methyl acetylide from methyl acetylene?
21. monosilver ethyl acetylide from ethyl acetylene?
V. Answer the following questions.
1. A gas X is obtained by treating calcium carbide with water. What is
gas X? Write down the equation.
Gas X can also be obtained by heating alkene dibromide and alcoholic
potassium hydroxide. Name the alkene dibromide. Write down the
equation.
Is the gas X saturated or unsaturated hydrocarbon? What type of
reaction can undergo (addition or substitution)?
2. A gas B is obtained by treating calcium carbide with water. What is
gas B? Write down the chemical equation.
Page-68
3. A gas Y is obtained by heating ethene dichloride with alcoholic

potassium hydroxide. What is gas Y? Write down the equation in
words and symbols.
4. A gas A is obtained by heating propene dibromide with alcoholic
potassium hydroxide. What is gas A? Write down the equation in
words and symbols.
5. A gas A is obtained by heating ethylidene bromide with alcoholic
potassium hydroxide. What is gas A? Write down the equation in
words and symbols.
6. A gas Y is obtained by heating n-propylidene bromide with alcoholic
potassium hydroxide. What is gas Y? Write down the equation in
words and symbols.
Alcohols
I. Complete the following compounds and name the organic
compounds.
𝑟𝑒𝑓𝑙𝑢𝑥
1. CH3-CH2Cl + KOH →
2. CH3-CH2- CH2Cl + KOH →
3. CH3-CH2-CH2SO4H + H2O →
4. CH3-CHSO4H-CH3 + H2O →
5. CH2=CH2 + H2SO4 →
6. CH2=CH2 + CH3-CH2SO4H →
7. CH3-CH2SO4H + H2O →
8. (CH3-CH2)2SO4 + H2O →
9. C6H10O5 + H2O →
10. C12H22O11 + H2O →
𝑦𝑒𝑎𝑠𝑡 𝑧𝑦𝑚𝑎𝑠𝑒
11. C6H12O6 →
12. CH3-CH2OH + Na →
13. CH3-CH2-CH2OH + Na →
14. CH3-CH2OH + PCl5 →
15. CH3-CH2-CH2OH + PCl5 →
𝐻2 𝑆𝑂4 ,1600 𝐶
16. CH3-CH2OH →
1000 𝐶
17. CH3-CH2OH + H2SO4 →
1400 𝐶
18. CH3-CH2SO4H + CH3-CH2OH →
Page-69
19. CH3-CH2OH + HCl →

𝐻 𝑆𝑂 (𝑐𝑜𝑛𝑐)
20. CH3-CH2OH + CH3COOH →
2 4
𝐻+
𝐶𝑢 3000 𝐶
21. CH3-CH2OH →
𝐶𝑢 3000 𝐶
23. CH3-CH2OH + [O] →
24. CH3-CHO + [O] →
II. What product would you expect when or what happen when
1. ethyl chloride is passed into reflux with an aqueous solution of KOH?
2. ethyl hydrogen sulphate is passed into reflux with water?
3. hydrocarbons with high molecular weight are cracked?
4. ethene reacts with concentrated sulphuric acid at 1600C?
5. ethene reacts with ethyl hydrogen sulphate?
6. ethyl hydrogen sulphate undergoes hydrolysis?
7. diethyl hydrogen sulphate undergoes hydrolysis?
8. the cooked starch is treated with malt for an hour at 600C?
9. starch is broken down with diastase?
10. maltose is hydrolyzed using yeast (maltase)?
11. glucose is broken down using yeast (zymase)?
12. a piece of sodium is added to ethanol?
13. ehanol reacts with PCl5 at room temperature?
14. ethanol reacts with hydrogen chloride in the presence of anhydrous
zinc chloride?
15. ethanol is heated with hydrogen chloride?
16. ethanol is heated with ethanoic acid in the presence of concentrated
sulphuric acid?
17. ethnol vapour is passed over freshly reduced copper at 3000C?
18. 1-propanol vapour is passed over freshly reduced copper at 3000C?
19. ethanol is oxidized with a mixture of potassium dichromate and dilute
sulphuric acid?
20. ethanal is oxidized with a mixture of potassium dichromate and dilute
sulphuric acid?
Page-70
III. Write equations to illustrate each of the following reactions.

1. Hydrolysis of ethyl bromide
2. Hydrolysis of ethyl hydrogen sulphate
3. Manufacture of ethanol from petroleum refinery products
4. Fermentation of maltose
5. Fermentation of glucose
6. Inorganic esterification (formation of inorganic ester)
7. Organic esterification (formation of organic ester)
8. Dehydrogenation of ethanol with copper
9. Oxidation of ethanol with acidified K2Cr2O7
IV. How would you prepare
1. ethanol from ethyl iodide?
2. propanol from iso-propyl hydrogen sulphate?
3. ethyl hydrogen sulphate from ethene?
4. diethyl sulphate from ethene?
5. ethanol from ethyl hydrogen sulphate?
6. ethanol from diethyl sulphate?
7. maltose from starch?
8. glucose from maltose?
9. ethanol from glucose?
10. sodium ethoxide from ethanol?
11. sodium propanoxide from 1-propanol?
12. ethyl chloride from ethanol?
13. ethene from ethanol?
14. diethyl ether from ethanol?
15. ethyl iodide from ethanol?
16. ethyl ethanoate from ethanol?
17. ethanal from ethanol?
18. propanal from 1-propanol?
19. ethanoic acid from ethanol?
V. Answer the following questions.
1. When ethyl iodide is refluxed with aqueous sodium hydroxide
solution, compound X is formed. What is compound X? Write down
the equation.
Page-71
2. When ethyl hydrogen sulphate is hydrolyzed, compound Y is formed.

What is compound Y? Write down the equation.
3. Compound A is obtained as a by product in cracking hydrocarbon with
very high molecular weight. What is compound A? Write down the
equation.
4. Compound B is formed when ethene reacts with ethyl hydrogen
sulphate. What is compound B? Write down the equation.
5. Compound X can be formed by the fermentation of starch with
enzyme, diastase. What is compound X? Write down the equation.
6. Compound A can be formed by the fermentation of maltose with
enzyme, maltase. What is compound A? Write down the equation.
7. A compound V is formed by adding sodium to ethanol at room
temperature. What is compound V? Write down the equation.
8. When compound B is treated with phosphorous (V) oxide, ethyl
chloride is obtained. What is compound B? Write down the equation.
9. Compound Y undergoes esterification with ethanoic acid and the final
product is ethyl acetate. What is compound Y? Write down the
equation.
10. Compound A is formed by the reaction of ethanol with hydrochloric
acid in the presence of zinc chloride. What is compound A? Write
down the equation.
11. When compound X is dehydrogenated using copper catalyst at 3000C,
ethanal is formed. What is compound X? Write down the equation.
12. The vapour of B gives ethanal when passed over freshly heated reduced
copper heated at 3000C.
Page-72
PETROLEUM INDUSTRY
AND
PETROCHEMICALS
(Crude Oil and other Fossil Fuels)
1. What is a fuel?
Fuel is a substance which stores the large amount of potential
energy.
2. What are the three major fossil fuels?
The three major fossil fuels are;
(i) crude oil (petroleum),
(ii) natural gas and
(iii) coal.
3. How are fossil fuels formed? Are these fuels renewable or non-
renewable resources?
Fossil fuels were formed in the earth’s crust from dead plants
and marine microorganisms under high temperature and pressure by
bacterial acting over millions of years. These fuels are non-renewable
and finite resources.
4. What are the sources of crude oil and natural gas, and coal?
The source of crude oil and natural gas is the dead bodies of
marine microorganisms. The source of coal is fossil plant materials.
5. What is crude oil?
Crude oil is one of the earth’s major natural resources. Crude
oil is a mixture of many different hydrocarbon molecules. In a refinery,
it is used to make fuels.
6. Explain the uses of crude oil?
Most of the crude oil is used to make fuel. Around 10% of
crude oil is used as feedstock or raw material in the chemical industry.
7. How do you separate the crude oil?
At a refinery, crude oil is separated into different fractions
consisting of groups of hydrocarbons that have different boiling points.
Page-73
8. What is the process used for the separation of crude oil? Which
type of apparatus is used in this separation?
The process used for the separation of crude oil is fractional
distillation process. The apparatus used is a fractional distillation
column or fractionating tower.
9. What are the various crude oil fractions?
Describe the various crude oil fractions by fractional distillation of
crude oil?
The various crude oil fractions are refinery gas, petrol
(gasoline), naphtha, paraffin (kerosene), diesel oil (gas oil), lubricating
oil, bitumen residue.
10. Describe the different fractions consisting of groups of
hydrocarbons. (OR)
What are the principal fractions obtained by the fractional
distillation of crude oil (petroleum)?
refinery gas (C1-C4) below 250C
viscosity increasing
petrol (gasoline) (C4-C12) 40-100
Boiling point and

Naphtha (C7-C14) 90-150
Paraffin (kerosene) (C9-C16) 150-240
diesel oil (gas oil) (C15-C25) 220-250
lubricating oil (C20-C70) 255-350
Bitumen (above C70) above 350
11. Mention the uses of petroleum gas, petrol, naphtha, paraffin, diesel
oil, lubricating oil and bitumen residue.
Fracitons Uses
Petroleum gas used as fuel
Petrol used as fuel in petrol engines
Naphtha used to make chemicals
Paraffin used as fuel in jet engines and for lighting and
heating
Diesel oil used as fuel in diesel engines
Lubrication oil used as engine oils
Bitumen residue used to make bitumen for surfacing roads
Page-74
12. Give the different terms used in the USA of the following names:
“crude oil”(UK), “petrol”(UK), “paraffin”(UK)
The different terms are used in UK and USA.
- “crude oil”(UK) is the same as “petroleum” in the USA.
- “petrol” (UK) is the same as “gasoline” in the USA.
- “paraffin” (UK) is the same as “kerosene” in the USA.
13. Arrange ‘kerosene, petrol, diesel oil’ in the increasing order of

their boiling points. Give ONE example of use for EACH of them.
petrol, kerosene, diesel oil
boiling point increases
Petrol (gasoline) is used as fuel in cars (petrol engines).
Kerosene (paraffin) is used as fuel in jet engines.
Diesel oil (gas oil) is used as fuel in diesel engines.
14. Arrange ‘lubricating oil, bitumen residue, naphtha’ in increasing
order of their boiling points and viscosity. Give ONE example of
use for EACH of them.
naphtha, lubricating oil, bitumen residue
boiling point and viscosity increase
Naphtha is used to make chemicals.
Lubricating oil is used as engine oils.
Bitumen residue is used to make bitumen for surfacing roads.
15. Describe how petrol is obtained from crude oil.
Petrol is obtained by the fractional distillation of crude oil
using fractionating distillation column or fractionating tower. Crude oil
is preheated to 350-4000C and pumped into the base of tower. As it
boils, the vapour passes up the tower. Crude oil is separated into
different fractions that have different boiling points. The different
fractions cool and condense at different temperatures. Petrol is
obtained from the top of the tower at the boiling range 40-1000C.
16. How do you understand by the term ‘diesel’?
Diesel is a heavy liquid fuel containing hydrocarbon molecule
(consisting of between 14 to 20 carbon atoms) which can power the
diesel engine.
Page-75
17. What is ‘catalytic cracking (cat cracking)?

The process in which large molecules from heavier fractions
can be broken down into smaller, more valuable molecules using
catalyst made of powdered minerals such as silica, alumina and zeolites
at a temperature around 5000C in huge reactor is called ‘catalytic
cracking (cat cracking).
18. Describe two types of products from all cracking reactions and
mention their uses.
All cracking reactions give two types of products:
(i) an alkane with a shorter chain than the original and
(ii) a shorter chain alkene molecule.
The shortened alkanes can be blended with gasoline fraction
to enrich the petrol. The alkenes are useful as raw materials for making
several important products.
19. Write equation to indicate how ethane can be made from petrol.
ℎ𝑒𝑎𝑡
C8C18 𝑐𝑎𝑡𝑎𝑙𝑦𝑠𝑡
4C2H4 + H2
petrol ethene
20. What happen when decane is cracked? Write equation in words
and symbols.
ℎ𝑒𝑎𝑡
C10C22 𝑐𝑎𝑡𝑎𝑙𝑦𝑠𝑡
C8H18 + C2H4
decane octane ethene
21. Write down the names of products which are made from ethene
produced by catalytic cracking?
The names of products which are made from ethene produced
by catalytic cracking are
(i) ethanol
(ii) polyethene (PE) or polyethylene
(iii) poly vinyl chloride (PVC) or chloroethene
(iv) polystyrene (PS) or phenylethene
22. What compound is added to gasoline to prevent engine knocking?
Tetraethyl lead is added to gasoline to prevent engine knocking.
Page-76
23. What is meant by ‘flash point’?

Flash point is the temperature at which the vapour will ignite
in air in the presence of a flame. This temperature is usually low for a
fuel. It is 110C for methanol.
24. What is meant by ignition temperature?
Ignition temperature is the temperature at which fuel/air
mixture ignites without a flame. It is 5500C for petrol. The flash point
is very much lower than the ignition temperature.
25. What are car exhaust fumes composed of?
Car exhaust fumes are composed of carbon dioxide, carbon
monoxide, unburnt hydrocarbons (HC), oxides of nitrogen and very
little sulphur dioxide. These fumes are reduced by fitting a catalytic
converter to the car exhaust.
26. What is meant by the terms ‘zeolite’ and ‘ZSM-5’?
Zeolite is one of a large group of alumino-silicates of sodium,
potassium, calcium and barium.
ZSM-5 is an artificial zeolite composed of aluminum, silicon
and oxygen.
27. How would you prepare the hydrocarbon (gasoline) from
methanol?
Methanol is first converted to methanol. The methanol
produced is then turned into hydrocarbons (gasoline) using zeolite
ZSM-5 catalyst.
𝒁𝑺𝑴−𝟓 (𝒛𝒆𝒐𝒍𝒊𝒕𝒆)
nCH3OH → (CH2)n + nH2O
methanol Gasoline water
28. What is meant by the term ‘biodiesel’? Mention its uses.
Biodiesel is derived from plant seed oil and animal oil. It can
be used as a substitute for diesel fuel. These oils have to be converted
to biodiesel by the chemical process known as “Transesterification”.
In Myanmar, it is used in power tractor engines, petrol-diesel
engines and electricity generating engines.
29. What are the alternative transport fuels?
Alternative transport fuels are biodiesel, diesel, LPG, CNG and
gasoline from methanol.
Page-77
30. Give the name of process which is used for conversion of biodiesel
from seed oil.
The process which is used conversion of biodiesel from seed
oil is “Transesterification”.
31. Explain the terms: transesterification and fractional distillation
Transesterification
In organic chemistry, tranesterification is the process of
exchanging the alkoxy group of an ester compound by another alcohol.
Fractional distillation
Fractional distillation is the separation of a liquid mixture into
fractions differing in boiling point by means of distillation using a
fractionating column.
32. What is petroleum gas?
Petroleum gas is a mixture of LPG (liquid petroleum gas) and
CNG (compressed natural gas).
33. What do the terms ‘LPG’ and ‘CNG’ stand for? Write their
compositions.
The term ‘LPG’ stands for liquid petroleum gas. It is composed
of propane and butane. The term ‘CNG’ stands for compressed natural
gas. It is composed of 90% methane gas.
34. What are the uses of LPG and CNG in Myanmar?
LPG is used in households, restaurants, hotels and motels for
cooking, frying and other heating systems. CNG is used in taxis, buses
and vehicles.
35. What is meant by the term ‘biomass’?
Biomass is the organic waste. When it decays in the absence
of air, methane is produced.
36. What is meant by the term ‘biogas’? How would you produce it?
Biogas is a mixture of methane and carbon dioxide. It is
produced naturally from the decay of cow dung and organic waste in
the absence of air by the help of anaerobic bacteria.
37. Mention the uses of biogas in Myanmar?
In Myanmar, biogas is used as a fuel for local industry and
used to power the electricity generating engines.
Page-78
38. There are FOUR stages in the conversion of fats or oil to biodiesel.
Explain each stage.
First Stage - preparation of nearly 100% pure methanol or
ethanol.
Second Stage - the addition of potassium hydroxide or sodium
hydroxide basic catalyst to the prepared pure
methanol or ethanol.
Third Stage - the treatment of the seed oil with the prepared
basic catalyst solution and the solution is heated
to 600C which is Transesterification Process
producing methyl or ethyl ester as the product
(biodiesel) of the reaction.
Fourth Stage - the removal of glycerine and sodium or
potassium salt of fatty acid (soap) from the
reaction mixture by washing with water and pure
biodiesel is separated out by using the biodiesel
processor.
39. How do you understand the term ‘coal’?
Coal is our most abundant fossil fuel. Coal is not a single
substance. It is a complex mixture of compounds that occur naturally
in varying grades. It has the approximate composition formula
C135H96O9NS.
40. What are the different kinds of coals?
Four different kinds of coals are;
(i) peat,
(ii) lignite (brown coal),
(iii) bituminous coal (soft coal) and
(iv) anthracite (hard coal).
41. Give the types of four steps in the coal-forming process.
ℎ𝑒𝑎𝑡 ℎ𝑒𝑎𝑡 ℎ𝑒𝑎𝑡
peat 𝑝𝑟𝑒𝑠𝑠𝑢𝑟𝑒
lignite 𝑝𝑟𝑒𝑠𝑠𝑢𝑟𝑒
bituminous 𝑝𝑟𝑒𝑠𝑠𝑢𝑟𝑒
Anthracite
coal
(not a (brown (soft coal) (hard coal)
coal) coal)
Page-79
42. Name the chemicals which can obtained from coal and mention
their uses.
The chemicals which can obtained from coal and their uses
are as follows:
(i) ammonia – for fertilizer
(ii) coal gas – for industrial heating
(iii) coal tar – for paints, dyes, creosote and pitch
(iv) coke – for iron and steel making, for home and
industrial heating
43. (i) Give a balanced symbolic equation for the complete
combustion of petrol (octane, C8H18).
(ii) What is the mass of one mole of octane C8H18?
(iii) The combustion of one mole of octane is 5500 kJ. The density
of octane is 0.7 gdm-3. Calculate the energy produced by one
litre (1000cm3) of octane.
25
(i) C8H18 + 2
O2 8CO2 + 9H2O
(ii) the relative molecular mass of C8H18 = 8(12) + 18(1)

= 114
mass of one mole of C8H18 = 114 g
(iii) mass of octane = density x volume

= 0.7 gdm-3- x 1000cm3
= 700 g
mass
mole of octane = molar mass
700 g
= 114 gmol−1
= 6.14 mol
1 mol of octane = 5500 kJ of energy
6.14 mol
6.14 mol of octane = 5500 kJ x 1 mol
= 33771 kJ
Page-80

Organic Chemistry Compiled by Saya Minn Thant

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SAYA MINN THANT (B.Ed.

Bond orders in organic compounds

Hydrocarbons are compounds which contain hydrogen and carbon only.

alkane alkene alkyne

alkane saturated unsaturated unsaturated

Page 1 Organic Chemistry

Prefixes for various numbers of carbon

Alkanes (ending with –ane)

Homologous Series (Molecular Formulae and Names) of Alkanes

Condensed structural Formulae of Alkanes

methane ethene ethyne ethanol

Alkyl Radicals (R- Groups) (ending with –yl)

Page 3 Organic Chemistry

Molecular formula Structural formulae

Energy and persistence conquer all things.

Page 4 Organic Chemistry

(1) Trivial System

Page 5 Organic Chemistry

(vi) CH3-CH2-CH2-CH2-CH3 = diethyl methane

Page 6 Organic Chemistry

(1) Trivial System

(i) CH2=CH2 = ethene

Page 8 Organic Chemistry

Condensed Structural Formulae of Alkynes

Try yourself from C5 to C10 .

Page 10 Organic Chemistry

(1) Trivial System (alkyl alcohol)

(2) IUPAC System or Geneva System

(vii) 3CH3-2CH-1CH2OH = 2-methyl propan-1-ol

Nomenclature of organic acids

Page 13 Organic Chemistry

Preparations, Physical Properties and

R-COONa + NaOH CaO R-H + Na2CO3

Page 14 Organic Chemistry

Chemical Properties of Alkanes

Page 15 Organic Chemistry

(1) Combustion of alkanes

Page 16 Organic Chemistry

Page 17 Organic Chemistry

Physical Properties of Alkenes

Page 18 Organic Chemistry

Using platinum or palladium catalyst

CH3-CH=CH2 + HBr → CH3-CHBr-CH3 + CH3-CH2-CH2Br

Page 20 Organic Chemistry

(4) Hydroxylation of alkene

Page 21 Organic Chemistry

(1) Laboratory method to prepare ethyne or acetylene from coke

Page 22 Organic Chemistry

(1) Addition reaction

Page 23 Organic Chemistry

Page 24 Organic Chemistry

2CH3-CH2-C≡CH + Cu2Cl2 + 2NH3 2CH3-CH2-C≡C-Cu ↓ + 2NH4Cl

2CH3-CH2-C≡CH + Ag2O + NH3 2CH3-CH2-C≡C-Ag ↓ + NH4OH

CH3-C ≡ C-CH3 + Ag2O + NH3 no reaction

Page 25 Organic Chemistry

R-CH2X + NaOH reflux R-CH2OH + NaX

CH3-CH2Cl + NaOH reflux CH3 -CH2OH + NaCl

(2) By the hydrolysis of alkyl hydrogensulphate

R-CH2-SO4H + H2O reflux R-CH2OH + H2SO4

CH3-CH2-SO4H + H2O reflux CH3-CH2OH + H2SO4

Page 26 Organic Chemistry

(3) Manufacture of ethanol from petroleum refinery products