U Naing Naing Aung (Chem), BEHS Kyaukkyi

CHAPTER – 14
Organic Chemistry
Organic Chemistry
Organic chemistry is the chemistry of carbon compounds in which there is at least one carbon
to carbon bond or carbon to hydrogen bond.
Hydrocarbon
Hydrocarbon are carbon compounds which contain carbon and hydrogen only.
Two types of hydrocarbons
(1) Saturated hydrocarbon (e.g., alkane)
(2) Unsaturated hydrocarbon (e.g., alkene and alkyne)

( )
∘
Note: (1) In hydrocarbon, carbon atom has four valence electron ∘ C ∘ and the bond order of
∘
carbon is four ¿¿
(2) In hydrocarbon, hydrogen atom has one valence electron (Hx) and the bond order of
hydrogen is one −H .
Alkanes
(1) General formula = Cn H2n+2 (n = 1, 2, 3, 4, ….)
(2) Type of hydrocarbon = saturated hydrocarbon
(3) Type of bond = single bond
(4) The first member = CH4 (methane)
(5) Type of reaction = substitution reaction (or) chlorination reaction
Number of alkane
Molecular Formula IUPAC name Physical state
CH4 Methane
C2H6 Ethane Colourless gases
C3H8 Propane
C4H10 Butane
C5H12 Pentane
C6H14 Hexane
C7H16 Heptane
C8H18 Octane Colourless liquid
C9H20 Nonane
C10H22 Decane

Molecular Formula Structural Formula Graphic Formula

H
¿
CH4 CH4 H−C−H
¿
H
H
¿
_ C H_
C2H6 CH3−¿CH3 H ¿ H
¿
H¿C
H

H H
¿ ¿
_C H _ C _
C3H8 CH3−¿CH2−¿CH3 H ¿ H
¿ ¿
H¿ H
C
H

H H
¿ ¿
_ C H _ C H_
C4H10 CH3−¿CH2−¿CH2−¿ CH3 H ¿ ¿¿ H
¿
H ¿ H C¿
C
H H

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 U Naing Naing Aung (Chem), BEHS Kyaukkyi

H H
¿ ¿
_C H _ C _
C5H12 CH3−¿CH2−¿CH2−¿ CH2−¿CH3 H ¿ H
¿ ¿
H¿ H
C
¿
H

Alkyl radicals (or) Alkyl group

The radicals derived from alkanes are called alkyl radicals. (OR) The groups derived form the
corresponding alkanes by removal of an H- atom are called alkyl groups.
one −H
→
yl

General formula = Cn H2n+1

e.g. (1) CH4 −H CH3

→

methane methyl
(2) C2H6 −H
→
C2H5 (or) – CH2 – CH3
ethane ethyl
(3) C3H8 −H
→
C3H7 (or) – CH2 – CH2 – CH3
propane propyl
(4) C4H10 −H C4H9 (or) – CH2 – CH2 – CH2 – CH3
→

butane butyl
(5) C5H12 −H C5H11 (or) – CH2 – CH2 – CH2 – CH2 – CH3
→

pentane pentyl
Alkenes (or) Olefins
(1) General formula = CnH2n (n= 2, 3, 4, …)
(2) Type of hydrocarbon = unsaturated hydrocarbon
(3) Type of bond = double bond (– C = C –)
(4) The first member = C2H4 (or) CH2 = CH2 (ethene)
(5) Type of reaction = addition reaction
Molecular Formula IUPAC name Structure formula
C2H4 ethene CH2=CH2
C3H6 propene CH3–CH=CH2
C4H8 butene CH3–CH2–CH=CH2
C5H10 pentene CH3–CH2–CH2–CH=CH2
C6H12 hexane CH3–CH2–CH2–CH2–CH=CH2
C7H14 heptane CH3–CH2–CH2–CH2–CH2–CH=CH2
C8H16 octene CH3–CH2–CH2–CH2–CH2–CH2–CH=CH2
C9H18 nonene CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH=CH2
C10H20 decene CH3–CH2–CH2–CH2–CH2–CH2–CH2– CH2–CH=CH2
ALKYNES
(1) General formula = CnH2n-2 (n= 2, 3, 4, …)
(2) Type of hydrocarbon = unsaturated hydrocarbon
(3) Type of bond = triple bond
(4) The first member = C2H2 (or) CH≡CH
(5) Type of reaction = addition reaction and substitution reaction
Molecular formula IUPAC name Structural formula
C2H2 ethyne acetylene CH≡CH
C3H4 propyne CH3–C≡CH
C4H6 butyne CH3–CH2–C≡CH
C5H8 penpyne CH3–CH2– CH2–C≡CH

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C6H10 hexyne CH3–CH2–CH2–CH2–C≡CH

C7H12 heptyne CH3–CH2–CH2–CH2–CH2–C≡CH
C8H14 octyne CH3–CH2–CH2–CH2–CH2–CH2–C≡CH
C9H16 nonyne CH3–CH2–CH2–CH2–CH2–CH2–CH2–C≡CH
C10H18 decyne CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH2–C≡CH
ALCOHOLS
(1) General formula = CnH2n+2O (or) CnH2n+1OH (n = 1, 2, 3, 4, …)
(2) Type of hydrocarbon = saturated hydrocarbon
(3) Type of bond = single bond with OH group
(4) The first member = CH3OH (methanol)
Molecular formula IUPAC name Structural formula
CH4O (or) CH3OH methanol CH3–OH
C2H6O (or) C2H5OH ethanol mobile liquids CH3–CH2–OH
C3H8O (or) C3H7OH propanol CH3–CH2–CH2–OH
C4H10O (or) C4H9OH butanol CH3–CH2–CH2–CH2–OH
C5H12O (or) C5H11OH pentanol CH3–CH2–CH2–CH2–CH2–OH
C6H14O (or) C6H13OH hexanol CH3–CH2–CH2–CH2–CH2–CH2–OH
C7H16O (or) C7H15OH heptanol oily liquids CH3–CH2–CH2–CH2–CH2–CH2–CH2–OH
C8H18O (or) C8H17OH octanol CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH2–OH
C9H20O (or) C9H19OH nonanol CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH2–OH
C10H22O (or) C10H21OH decanol CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH2–OH

Alcohols, CnH2n+2 (or)

Alkanes, CnH2n+2 Alkenes, CnH2n Alkynes, CnH2n-2
CnH2n+1OH
Molecular IUPAC Molecular IUPAC Molecular IUPAC Molecular IUPAC
Formula Names Formula Names Formula Names Formula Names
CH4 methane - - - - CH3OH methanol
C2H6 ethane C2H4 ethene C2H2 ethyne C2H5OH ethanol
C3H8 propane C3H6 propene C3H4 propyne C3H7OH propanol
C4H10 butane C4H8 butene C4H6 butyne C4H9OH butanol
C5H12 pentane C5H10 pentene C5H8 pentyne C5H10OH pentynol
C6H14 hexane C6H12 hexene C6H10 hexyne C6H13OH hexanol
C7H16 heptane C7H14 heptene C7H12 heptyne C7H15OH heptanol
C8H18 octane C8H16 octene C8H14 octyne C8H17OH octanol
C9H20 nonane C9H18 nonene C9H16 nonyne C9H19OH nonanol
C10H22 decane C10H20 decene C10H18 decyne C10H21OH decanol

Structural isomers and structural isomerism

Compounds having the same molecular formula but different structural formulae have different
physical and chemical properties and are said to be structural isomers. The phenomenon is known as
structural isomerism.
e.g., Two isomers of butane (1) CH3CH2CH2CH3 (n-butane)
CH 3 ⸜
(2) CH-CH3 (iso-butene)
CH 3 ⸝
Three isomers of butane (1) CH3CH2 CH = CH2 (1-butene)
(2) CH3CH CH = CH3 (2-butene)
CH 3 ⸜
(3) C-CH2 (iso-butene)
CH 3 ⸝
Four isomers of butane (1) CH3CH2CH2CH2OH (butan -1 -ol or 1-butanol)

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(2) CH3CH2CHOHCH3 (butan -2 -ol or 2-butanol)

CH 3 ⸜
(3) CH CH2OH (2-methyl propan-1 -ol)
CH 3 ⸝
CH 3
¿
(4) CH3¿ C _ OH (2-methyl propan-2 -ol)
¿
CH 3

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 U Naing Naing Aung (Chem), BEHS Kyaukkyi

Preparation of alkanes
(A) Laboratory method of preparation
CaO
RCOONa + NaOH → RH + Na2CO3
△
Sodium alkanoate soda-lime alkane
CaO
(CnH2n+1) COONa + NaOH → CnH2n+2 + Na2CO3
△
Sodium alkanoate soda-lime alkane
 When sodium ethanoate is heated with soda-lime, methane is formed.
CaO
CH3COONA + NaOH → CH4 + Na2CO3
△
Sodium ethanoate soda lime methane
 When sodium propanoate is heated with soda-lime, ethane is formed.
CaO
CH3–CH2–COONa + NaOH → CH3–CH3 + Na2CO3
△
Sodium propanoate soda lime ethane
 When sodium butanoate is heated with soda-lime, propane is formed.
CaO
C3H7COONa + NaOH → C3H8 + Na2CO3
△
Sodium butanoate soda lime propane
 When sodium pentanoate is heated with soda-lime, butane is formed.
CaO
C4H9COONa + NaOH → C4H10 + Na2CO3
△
Sodium pentanoate soda lime butane
(B) Reduction of alkyl halides
 When alkyl halides is reduced with hydrogen molecules in the presence of Pt (or) Pd,
alkane is formed.
RX + H2 Pt ( ¿ ) Pd RH + HX
→
alkyl halide alkane
(X = Cl, Br, I)
 When methyl iodine is reduced with hydrogen molecules in the presence of Pt (or) Pd,
methane is formed.
CH3I + H2 Pt ( ¿ ) Pd CH4 + HI
→
Methyl iodine methane
 When methyl chloride is reduced with hydrogen molecules in the presence of Pt (or) Pd,
methane is formed.
CH3Cl + H2 Pt ( ¿ ) Pd CH4 + HCl
→
Methyl chloride methane
 When methyl bromide is reduced with hydrogen molecules in the presence of Pt (or) Pd,
methane is formed.
CH3Br + H2 Pt ( ¿ ) Pd CH4 + HBr
→
Methyl bromide methane
 When ethyl iodide is reduced with hydrogen molecules in the presence of Pt (or) Pd,
ethane is formed.
CH3–CH2–I + H2 Pt ( ¿ ) Pd CH3–CH3 + HI
→
Ethyl iodide ethane
 When ethyl chloride is reduced with hydrogen molecules in the presence of Pt (or) Pd,
ethane is formed.
CH3–CH2–Cl + H2 Pt ( ¿ ) Pd CH3–CH2 + HCl
→
Ethyl chloride ethane
 When ethyl bromide is reduced with hydrogen molecules in the presence of Pt (or) Pd,
ethane is formed.

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CH3–CH2–Br + H2 Pt ( ¿ ) Pd CH3–CH3 + HBr

→
Ethyl bromide ethane
(C) When alkyl iodine is reduced with hydrogen iodine, alkane is formed.
RI + HI → RH + I2
alkyl iodine alkane
 When ethyl iodine is reduced with hydrogen iodine, ethane is formed.
CH3CH2I + HI → CH3CH3 + I2
Ethyl iodine ethane
 When methyl iodine is reduced with hydrogen iodine, methane is formed.
CH3I + HI → CH4 + I2
Methyl iodine methane
 When n-propyl iodine is reduced with hydrogen iodine, propane is formed.
CH3–CH2–CH2 I + HI → CH3CH2CH3 + I2
n-propyl iodine propane
(D) Reduction of alkenes (or) Hydrogenation
 When alkene is heated with hydrogen in the presence of nickel at 3000C, alkane is formed.
R CH = CH2 + H2 ¿ , 300 ℃ R CH2–CH3
→
alkane
CnH2n + H2 ¿ , 300 ℃ CnH2n+2
→
alkene alkane
 When ethene is heated with hydrogen in the presence of nickel at 3000C, ethane is formed.
CH2 = CH2 + H2 ¿ , 300 ℃ CH3 – CH3
→
Ethene ethane
 When propene is heated with hydrogen in the presence of nickel at 300 0C, propane is
formed.
CH3 – CH = CH2 + CH2 + H2 ¿ , 300 ℃ CH3–CH2–CH3
→
Propene propane
 When n-butene is reduced with hydrogen in the presence of nickel at 200 0C, butane is
formed.
CH3CH2CH = CH2+ H2 ¿ , 300 ℃ CH3CH2CH2 – CH3
→
Butene butane
 When 2-butene is reduced with hydrogen in the presence of nickel at 200 0C, butane is
formed.
CH3 – CH = CH – CH3 + H2 ¿ , 300 ℃ CH3 – CH2 – CH2 – CH3
→
2-butene butane
Chemical properties
Chlorination reaction
diffused
CH4 + Cl2 → CH3Cl + HCl
sunlight
Methane methyl chloride
diffused
CH3Cl + Cl2 → CH2Cl2 + HCl
sunlight
methyl chloride
diffused
CH2Cl2 + Cl2 → CHCl3 + HCl
sunlight
chloroform
diffused
CHCl3 + Cl2 → C Cl4 + HCl
sunlight
carbon tetrachloride

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Preparation of alkenes
(1) Dehydration of alcohols
 When alcohol is heated with concentrated sulphuric acid at 1600C alkene is formed.
RCH CH OH H2 SO4 , 160°C RCH = CH + H O
2 2 2 2
→
Alcohol alkene
 When alcohol is heated with alumina at 3500C alkene is formed.
RCH CH OH Al2 O3 , 350°C RCH = CH + H O
2 2
→
2 2

Alcohol alkene
 When ethanol is heated with concentrated sulphuric acid at 1600C ethene is formed.
CH CH OH H2 SO4 , 120°C CH = CH + H O
3 2
→
2 2 2

ethanas ethene
 When ethanol is heated with alumina at 3500C ethene is formed.
CH CH OH Al2 O3 , 350°C CH = CH + H O
3 2
→
2 2 2

Alcohol ethene
 When propanol is heated with concentrated sulphuric acid at 1600C propene is formed.
CH CH OH H2 SO4 , 160°C CH = CH + H O
3 2 3 2 2
→
propanol propene
 When propanol is heated with alumina at 3500C propene is formed.
CH CH CH OH Al2 O3 , 350°C CH CH = CH + H O
3 2 2
→
3 2 2

propanol propene
(2) Dehydrohalogenation of alkyl halides
 When Alkyl halides is heated with an alcoholic solution of postassium hydroxide on a
water, alkene is formed.
ethanol
RCH2CH2X + KOH → RCH = CH2 + KX + H2O
△
n – alkyl halides alkene
ethanol
RCHX CH3 + KOH → RCH = CH2 + KX + H2O
△
sec – alkyl halides alkene
(secondary alkyl halides)
 When ethyl choloride is heated with an alcoholic solution of potassium hydroxide on a
water bath, ethen is formed.
ethanol
CH3CH2Cl + KOH → CH2 = CH2 + KCl + H2O
△
Ethyle chloride ethene
 When ethyl bromide is heated with an alcoholic solution of potassium hydroxide on a water
bath, ethene is formed.
ethanol
CH3CH2Br + KOH → CH2 = CH2 + KBr + H2O
△
Ethyle bromide ethene
 When n-propyl chloride is heated with an alcoholic solution of potassium hydroxide is a
water both prpene is formed.
ethanol
CH3CH2 CH2Cl + KOH → CH3CH = CH2 + KCl + H2O
△
n-propyl chloride Propene
 When n-propyl bromide is heated with an alcoholic solution of postassium hydroxide a
water bath, propene is formed.
ethanol
CH3CH2 CH2Br + KOH → CH3CH = CH2 + KBr + H2O
△
n-propyl bromide bromine

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 When iso-propyl chloride is heated with an alcoholic solution of potassium hydroxide is a

water bath, propene is heated
ethanol
CH3CHCLCH3 + KOH → CH3CH = CH2 + KCl + H2O
△
iso-propyl chloride propene
 When iso-propyl bromide is heated with an alcoholic of potassium hydroxide is a water
bath, propene is heated.
ethanol
CH3CHBrCH3 + KOH → CH3CH = CH2 + KBr + H2O
△
iso-propyl bromide prpene

Chemical properties of alkene

1) Addition of hydrogen (Hydrogenation)
RCH = CH2 + H2 Pt ∨Pd RCH2CH3
→
alkene alkane
¿
RCH = CH2 + H2 → RCH2CH3
200−300℃
alkene alkane
(1) When ethene is reacted with hydrogen in the presence of Pt (or) Pd, ethane is formed.
CH2 = CH2 + H2 Pt ∨Pd CH3 – CH3
→
ethene ethane
(2) When propene is reacted with hydrogen in the presence of Pt (or) Pd, propane is formed.
CH3CH = CH2 + H2 Pt ∨Pd CH3CH2CH3
→
propene propane
(3) When ethene is reacted with hydrogen in the presence of nickel at 200-3000C, ethane is formed.
¿
CH2 = CH2 + H2 → CH3 = CH3
200−300℃
ethene ethane
(4) When propene is reacted with hydrogen in the presence of nickel at 200-300 0C, propane is
formed.
¿
CH3CH = CH2 + H2 → CH3CH2CH3
200−300℃
propene propane
(5) When 2-butene is reacted with hydrogen in the presence of Pt (or) Pd, butane is formed.
CH3CH = CH CH3 + H2 Pt ∨Pd CH3CH2CH2CH3
→
2-butene butane
(6) When 2-butene is reacted with hydrogen in the presence of nickel at 200-300 0C, butane is
formed.
¿
CH3CH = CH CH3 + H2 → CH3CH2CH2CH3
200−300℃
2-butene butane
2) Addition of chlorine and bromine (halogenation)
R CH = CH2 + X2 ⟶ R CH X∘ CH2 X
alkene (x = Cl, Br) alkene dihalide
(1) ■ When ethene is passed into chlorine, ethene dichloride is formed.
CH2 = CH2 + Cl ⟶ CH2Cl – CH2Cl
ethene ethene dichloride
 When ethene is passed into bromide, ethene dibromide is formed.
CH2 = CH2 + Br ⟶ CH2Br – CH2Br
ethene ethene dibromide
(2) ■ When propene is passed into chlorine, propene dichloride is formed.
CH3 CH = CH2 + Cl2 ⟶ CH3CH Cl – CH2Cl
propene propene dichloride

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■ When propene is passed into bromine, propene dibromide is formed.

CH3 CH = CH2 + Br2 ⟶ CH3CH Br CH2Br
propene propene dibromide
■ When butene is passed into chlorine, butene dichloride is formed.
CH3CH2CH = CH2 + Cl ⟶ CH3CH2CH Cl CH2Cl
butene butene dichloride
■ When butene is passed into bromine, butene dibromide is formed.
CH3CH2CH = CH2 + Br ⟶ CH3CH2CH Br – CH2Br
butene butene dibromide
■ When 2-butene is passed into chlorine, butene dichloride is formed.
CH3CH = CH CH3 + Cl2 ⟶ CH3CH Cl – CH Cl CH3
2-butene butene dichloride
■ When 2-butene is passed into bromine, butene dibromide is formed.
CH3CH = CH CH3 + Br2 ⟶ CH3CH Br – CH Br CH3
2-butene butene dibromide
3) Addition of hydrogen halides or halogen acids
CH2 = CH2 + HX ⟶ CH3CHX
ethene ethyl halide
CH3CH = CH2 + HX ⟶ CH3CH X ∘ CH3 + CH3CH2CH2X
propene iso-propyl halide (major prduct) n-propyl halide (minor product)
Markownikoff’s rule
When an unsymmetrical addendum (HX) adds on to an unsymmetrical alkene, two products are
possible but that product where the negative part of the addendum adds on to the carbon with the least
number of hydrogen atoms is the major product.
e.g., CH3CH = CH2 + HX ⟶ CH3CH2CH2X + CH3CH X CH3
propene (x = Cl, Br, I) n-propyl halide(minor prodcut) isopropyl halide(major
product) (1) When ethene is reacts with hydrogen chloride, ethyl chloride is formed.
CH2 = CH2 + HCl ⟶ CH3CH2Cl
ethene ethyl chloride
(2) When ethene reacts with hydrogen bromide, ethyl bromide is formed.
CH2 = CH2 + HBr ⟶ CH3CH2Br
ethene ethyl bromide
(3) When ethen reacts with hydrogen iodide, ethyl iodide is formed.
CH2 = CH2 + HI ⟶ CH3CH2I
ethene ethyl iodide
(4) When propene reacts with hydrogen chloride, propyl chloride is formed.
CH3CH = CH2 + HCl ⟶ CH3CH Cl∘CH3 + CH3CH2CH2Cl
propene iso-propyl chloride n-propyl chloride
(major product) (minor product)
(5) When propene reacts with hydrogen bromide propyl bromide is formed.
CH3 CH = CH2 + HBr ⟶ CH3CH Br – CH3 + CH3CH2CH2Br
propene iso-propyl bromide n-propyl bromide
(major product) (minor product)
(6) CH3CH = CH2 + HI ⟶ CH3CH I CH3 + CH3CH2CH2I
propene iso-propyl iodide n-propyl iodide
(major product) (minor product)
When iso-butene reacts with hydrogen chloride
■ CH3 C = CH2 + HCl ⟶ CH3C Cl CH3 + CH3CH CH2Cl
| | |
CH3 CH3 CH3
iso-butene tertiary-butyl chloride iso-butyle chloride
(major product) (minor product)
■ CH3 C = CH2 + HBr ⟶ CH3C Br CH3 + CH3CH CH2Br
| | |
CH3 CH3 CH3
iso-butene tertiary-butyl bromide iso-butyle bromide
(major product) (minor product)
■ CH3 C = CH2 + HCl ⟶ CH3C Cl CH3 + CH3CH CH2Cl
| | |

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CH3 CH3 CH3

iso-butene tertiary-butyl chloride iso-butyle chloride
(major product) (minor product)

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 U Naing Naing Aung (Chem), BEHS Kyaukkyi

4) Formation of ozonide and ozonolysis

■ When ozonized oxygen is passed into ethene in chloroform and the product is decomposed by water,
metanal is formed.
O
/ \
CH3=CH2 + O3 Chloroform CH2 CH2 + H2O Zn → dust 2HCHO + H2O2
→
| |
O –– O
ethene ozone methanol
■ When ozonized oxygen is passed into propene in chloroform and the product is decomposed by
water.
O
/ \
CH3CH=CH2 + O3 Chloroform CH3–CH CH2 Zn → dust H CH O + CH3CH O + H2O2
→
| |
O –––– O
ethene ozone propene ozonide methanal ethanal

5) Xydroxylation of alkenes
■ When alkene is passed into cold dilute potassium permanganate solution, alkene glycol is formed.

R CH = CH + H O + [O] 1 % KMn O4 R CHOH – CH OH

2 2 2
→
alkene water nascent oxygen alkene glycol
■ When ethene is passed into cold dilute potassium permanganate solution, ethene glycol is formed.

CH = CH + H O + [O] 1 % KMn O4 CH OH = CH OH
2 2 2 2 2
→
ethene water nascent oxygen ethene glycol
■ When propene is passed into cold dilute potassium permaganate solution, propene glycol is formed.

CH CH = CH + HO + [O] 1 % KMn O4 CH CHOH = CH OH

3 2 2 3 2
→
propene water nascent oxygen ethene glycol

Decolourization of bromine solution

■ When ethene is passed into a 1% solution of Br2 in carbon tetrachloride.

CH = CH + Br2 C Cl 4 CH Br . CH Br
2 2 2 2
→
ethene raddish brown ethene dibromide (colurless)

ALKYNES
1) Preparation of alkynes (acetylene) from carbon
■ When calcium oxide is heated with coke in an electric furnace,
CaO + 3C electric furnace CaC2 + CO
→
calcium oxide coke calcium carbide
■ When calcium carbide is treated with water,
CaC2 + 2H2O → CH≡CH + Ca (OH)
calcium carbide ethyne

2) Dehydrohalogenation of ethene dibromide (or) ethylidene chloride

■ When ethene dibromide is heated with alcoholic potassium hydroxide, ethyne is formed.
ethanol
CH2Br CH2Br + 2KOH → CH≡CH + 2KBr + 2H2O
△
ethene dibromide ethyne
■ When ethylidene chloride is heated with alcoholic potassium hydroxide, ethyne is formed.
ethanol
CH3CH Cl2 + 2KOH → CH≡CH + 2K Cl + 2H2O
△
ethene chloride ethyne

Chemical properties of alkynes

1) Addition of hydrogen (Hydrogenation)
■ When alkyne reach with hydrogen in the presence of platinum, alkane is formed.
CnH2n-2 + H2 Pt / Pd CnH2n
→
+ H2 Pt / Pd CnH2n+2 →

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alkyne alkene alkane

R.C≡CH + H2 Pt / Pd R.CH≡CH2 + H2 Pt / Pd RCH2–CH3
→ →
alkyen alkene alkane
■ When ethyne reach with hydrogen in the presence of platinum or palladium, ethane is formed.
CH≡CH + H2 Pt / Pd CH2=CH2 + H2 Pt / Pd CH3–CH3
→ →
ethyne ethene ethane
■ When propyne reach with hydrogen in the presence of platinum or palladium, propane is
formed.
CH3–C ≡ CH + H2 Pt / Pd CH3CH=CH2 + H2 Pt →/ Pd CH3CH2CH3
→
1- butyne
■ When 1-butyne reach with hydrogen in the presence of platinum or palladium, butane is
formed.
CH3–C ≡ CH + H2 Pt / Pd CH3CH2CH=CH2 + H2 Pt / Pd CH3CH CH2-CH3
→ →
1-butyne 1-butene 1-butene
■ When 2-butyne reach with hydrogen in the presence of platinum or palladium, butane is
formed.
CH3–C ≡ C–CH3 + H2 Pt / Pd CH3–CH = CH–CH3 + H2 Pt / Pd CH3–CH2=CH2–CH3
→ →
Butyne butene butane
2) Addition of halogens (Halogenation)
R.CH2C≡CH + X2 → RCH2CX = CHX + X2 → R CH2CX2CH X2
alkyne (x=Cl, Br, I) alkyne dihalide alkyne
tetra.halide
■ When ethyne is reacted with chlorine in the dark by the presence of catalyst,
CH≡CH + Cl2 light →
CH Cl=CH Cl + Cl2 light →
CH Cl2 CH Cl2
Ethyne ethyne dichloride ethyne tetra.chloride
■ When ethyne is reacted with liquid bromine in the absence of solvent,
CH≡CH + Br2 → CH Br = CH Br + Br2 → CH Br2CH Br2
Ethyne ethyne dibromide ethyne tetra bromide
■ When ethyne add on iodine
CH≡CH + I2 ethanol →
CH I = CH I
ethyne ethyne di.iodide
CH3C≡CH + Cl2 light CH3C Cl=CH Cl + O2 light CH3C Cl2CH Cl2
→ →
propyne propyne di.chloride propyne tetra.chloride
CH3C≡CH + Br2 → CH3C Br = CH Br + Br2 → CH3C Br2CH Br2
propyne propyne dibromide propyne tetra.bromide
CH3C≡CH + I2 ethanol
→
CH3 C I = CH I
propyne propyne di.iodide
3) Addition of the hydrogen halide or halogen acids, HX (hydrohalogenation)
■ When ethyne reacts with an escess of HBr in the presence of light and metallic halide,
light
CH≡CH + HBr → CH2 = CH Br
metallic halide
ethyne vinyl bromide
light
CH2 = CH Br + H Br → CH3–CH Br2
metallic halide
ethylidene bromide
■ When ethyne reacts with an escess of HCl in the presence of light and metallic halide,
light
CH≡CH + H Cl → CH2 = CH Cl
metallic halide
ethyne vinyl chloride
light
■ CH2 = CH Br + H Br → CH3 – CH Br2
metallic halide

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 U Naing Naing Aung (Chem), BEHS Kyaukkyi

ethylidene bromide
■ When ethyne reacts with an escess of HCl in the presence of light and metallic halide,
light
CH≡CH + HCl → CH2 = CH Cl
metallic halide
ethyne vinyl chloride
light
CH2 = CH Cl + H Cl → CH3 – CH Cl
metallic halide
Ethyldene chloride

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 U Naing Naing Aung (Chem), BEHS Kyaukkyi

■ When 1-butyne reacts with excess HBr

light
CH3–CH2–C≡CH + H Br → CH3CH2C Br=CH2
metallic halide
1-butyne 2-bromo 1-butene
light
CH3CH2C Br = CH2 + H Br → CH3CH2C Br–CH3
metallic halide
1-butyne 2, 2-dibromo butane
4) Addition of the elements of water (Hydration)
When acetylene is passed into dilute sulphuric acid containging mercury (II) sulphate at 600C.
H 2 SO4 , 60 °
CH≡CH + H2O [CH2 = CH OH] → CH3CH O
¿
ethyne (or) acetylene vinyl alcohol (unstable) ethanal
(acetaldehyde)
H 2 SO4 , 60 °
CH3–C≡CH + H2O [CH3CH=CH OH] → CH3CH2CH O
¿
propyne propen-1-0-1 (unstable) propanal
5) Substitution reactions
■ When acetylene is passed over heated sodium,
CH≡CH + 2Na → Na C≡C Na + H2
Ethyne (or) acetylene disodium acetylide
1
CH3C≡CH + Na → CH3C≡C Na + H
2 2
propyne methyl sodium acetylide
1
CH3CH2C≡CH + Na → CH3CH2C≡C Na + H
2 2
1-butyne ethyl sodium acetylide
CH3–C≡C–CH3 + Na → No reaction
2-butyne
■ When ethyne is passed into an ammoniacal solution of copper (I) chloride,
CH3≡CH + Cu2Cl2 → Cu C≡C Cu↓ + 2NH4Cl
ethyne (or) acetylene dicopper acetylide (red, ppt)
1
CH3C≡CH + Cu2Cl2 + NH3 → CH3C≡C Cu↓ + NH4Cl
2
propyne methyl copper acetylide(red, ppt)
1
CH3–CH–C≡CH + Cu2Cl2 + NH3 → CH3CH2C≡C Cu↓ + NH4Cl
2
1-butyne
CH3–C=C–CH3 + CuCl2 + NH3 → no reaction
2-butynea
■ When ethyne is passed into an ammonical solution of silver oxide
CH≡CH + Ag2O + NH3 → AgO≡C Ag↓ + NH4OH
ethyne (or) acetylene disilver acetylide(white ppt)
2CH3C≡CH + Ag2O + NH3 → 2CH3C≡C Ag↓ + NH4OH
propyne (or) methyl acetylene methyl silver acetylide (white ppt)
2CH3–CH2–C≡CH + Ag2O + NH3 → 2CH3CH2C≡C Ag↓ + NH4OH
1-butyne (or) ethyl acetylene ethyl silver acetylide (white ppt)
CH3 – C≡C CH + Ag2O + NH3 → no reaction
2-butyne (or) dimethyl acetylene
Preparation of Alcohols
1) By the hydrolysis of alkyl halides
When alkyl halide is heated under reflux with aqueous sodium (or) potassium hydroxide
soloution.
reflux
R CH2X + NaOH → RCH2OH + NaOH
△
alkyl halide Alcohol
reflux
R CH2X + KOH → RCH2OH + KX
△
alkyl halide alcohol

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 U Naing Naing Aung (Chem), BEHS Kyaukkyi

■ When ethyl chloride is heated under reflux with aqueous sodium hydroxide.
reflux
CH3CH2Cl + Na OH → CH3CH2OH + NaCl
△
ethyl chloride ethanol

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 U Naing Naing Aung (Chem), BEHS Kyaukkyi

reflux
CH3CH2Br + Na OH → CH3CH2OH + Na Br
△
ethyl bromide ethanol
reflux
CH3CH2Cl + K OH → CH3CH2OH + K Cl
△
ethyl chloride ethanol
reflux
CH3CH2Br + K OH → CH3CH2OH + K Br
△
ethyl bromide ethanol
2) By the hydrolysis of alkyl hydrogensulphate
■ When ethyl hydrogensulphate is heat under reflux with water,
reflux
CH3CH2SO4H + H2O → CH3CH2OH + H2SO4
△
ethyl hydrogensulphate ethanol
Menufacture of ethanol from petroleum refinery products
■ Ethene is treated with sulphuric acid.
CH2=CH2 + H2SO4 → CH3CH2SO4H
ethene ethyl hydrogen sulphate
CH2=CH2 + CH3CH2SO4H → (CH3CH2)2SO4
ethene ethyl hydrogensulphate diethyl sulphate
CH2=CH2 + CH3CH2SO4H → (CH3CH2)2SO4
ethene ethyl hydrogen sulphate diethyl sulphate
■ These products are hydrolysed.
CH3CH2SO4H + H2O → CH3CH2OH + H2SO4
ethyl hydrogen sulphate ethanol
■ (CH3CH2)2SO4 + 2H2O → 2CH3CH2OH + H2SO4
Diethyl sulphate ethanol

Manufacture of ethanol by fermentation

■ Starch is cooked under pressure. It is cooled and treated with enzyme diastase from germinated
barley for (1)hour at 600C.
n n
(C6H10O5)n + H O diastase C H O
2 2 → 2 12 22 11
starch maltose
■ Maltose is treated by enzyme altase from yeast.
yeast
C12H22O11 + H2O → 2C6H12O6
(maltase)
maltose glucose
■ Glucose is treated with enzyme zymase from yeast.
yeast
C6H12O6 → 2CH3CH2OH + 2CO2↑
zymase
glucose ethanol

Chemical properties of Alcohol

(a) Reaction with metallic sodium
■ When a piece of sodium is added to ethanol,
1
CH3CH2OH + Na → CH3CH2O Na + H
2 2
ethanol sodium ethoxide
■ When a piece of sodium is added to methanol
1
CH3OH + Na → CH3O Na + H
2 2
methanol sodium methoxide
Reaction with PCl5
(b) When Cl5 is reacts with ethanol at room temperature,

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 U Naing Naing Aung (Chem), BEHS Kyaukkyi

■ CH3CH2OH + PCl5 → CH3CH2Cl↑ + PO Cl3 + H Cl↑

ethanol ethyl chloride
■ CH3OH + PCl5 → CH3Cl↑ + POCl3 + H Cl↑
methanol methyl chloride

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 U Naing Naing Aung (Chem), BEHS Kyaukkyi

■ C3H7OH + PCl5 → C3H7Cl↑ + POCl3 + H Cl↑

propanol propyl chloride
■ C4H9OH + PCl5 → C4H9Cl↑ + POCl3 + H Cl↑
butanol butyl chloride

(c) Reaction with sulphuric acid

■ When ethanol is heated with and excess of concentrated sulphuric acid at 1000C,
CH3CH2OH+ H2SO4 100 ℃ →
CH3CH2SO4H + H2O
ethanol ethyl hydrogen sulphate
■ When ethanol is heated with and excess of concentrated sulphuric acid at 1400C,
H 2 SO 4
2CH3CH2OH → CH3CH2O CH2CH3 + H2O
140 °
diethyl ether
Reaction of etahnol with HI, HBr and HCl
■ When ethanol reacts with HI,
CH3CH2OH + HI → CH3CH2I + H2O
ethanol ethyl iodide
■ When ethanol reacts with HBr,
CH3CH2OH + H Br → CH3CH2Br + H2O
ethanol ethyl bromide
■ When ethanol reacts with H Cl,
CH CH OH
3 2 + HCl ZnCl 2 CH CH Cl
→
3 +2 HO 2

ethanol ethyl chloride

Formation of esters (Esterification)

■ When ethanol reacts with ethanoic acid (acetic acid) in the presence of small amount of
concentrated sulphuric acid,
H 2 SO 4
CH3COOH + CH3CH2OH CH3COO CH2CH3 + H2O
¿
ethanoic ethanol ethyl ethanoate (ethyl acetate)

Oxidation (Dehydrogenation)
■ When etanol is passed over freshly reduced copper heated at 3000C,
CH3CH2OH Cu300 ° C CH3CHO + H2
→
ethanol (vapour) ethanal (acetaldehyde)

Oxidation by oxidiaing mixtures

When ethanol is heated with a mixture of potassium dichromate and dilute sulphuric acid,
→
■ CH3CH2OH + [O] K 2 Cr2 O7 ¿ dil H 2 SO 4 CH3CHO + H2O
+¿

ethanol ethanal
→
■ CH3CHO + [O] K 2 Cr2 O7 ¿ dil H 2 SO 4 CH3COOH
+¿

ethanal ethanoic acid

Polymerization
¿ 100 atm
n (CH2=CH2) → ( CH2 – CH2 ) n
△
ethene polyethene

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