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LECTURE NOTES
Session - 2009-10

ORG NIC CHEMISTRY

TOPIC : ALKENE & ALKYNE

Contents : Alkene/Alkyne

Lect.
1 Physical properties of Alkenes/Alkyne
2 Relative Besicity
3 Lab test of alkene and alkynes
4 Stability of alkenes/cycloalkenes
5 Method of preparation
(A) By partial reduction of alkynes
(B) Dehydration of alcohol
Lect.
(H) Acid-Catalyzed Hydration
(i) For Alkene
(a) Oxymercuration-Demercuration
(b) Alkoxymercuration - demercuration
(c) Hydroboration-oxidation (Syn addition)
(ii) Acid-Catalyzed Hydration For Alkyne
Examples

(C) By pyrolysis of esters

Examples Lect.
(I) Oxidation Reaction
Lect. (i) Ozonolysis (C = C, C C)
(D) By Dehalogenation of vicinal dihalides/ Examples
tetrahalides
(E) Dehydrohalogenation of alkyl halides/
vicinal dihalides
Lect.
(F) Replacement of the acetylenic hydrogen (ii) Hydroxylation Reactions (Alkenes, Alkynes)
atom of terminal alkynes to form higher (iii) Epoxidation of Alkenes
alkynes (iv) Oxidative cleavage (Alkenes, Alkynes)
(G) Miscellaneous Examples
Hydrolysis of carbides

Examples Lect.
7. Miscelleneous
Lect.
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7. Miscelleneous
Lect. (A) Addition of carbenes to Alkenes
6. Chemical Reactions (B) Addition of NOCl
(A) Electrophilic addition reaction (C) Halogenation. Allylic substitution
(B) Addition of halogen to alkenes (D) Alkylation
(C) Addition of halogen to alkynes Examples
(D) Addition of HOX to Alkene
(E) Addition of HOX to Alkynes
Examples
Lect.
Discussion

Lect.
(F) Addition of Hydrogen Halides (+ HX) to Alkene
(G) Addition of Hydrogen Halides (+ HX) to Alkyne
Examples

Page 2

Physical properties of alkenes & General method of preparation of alkenes

1. Physical Properties of Alkenes

TABLE : 1

Physical properties Homologus series Isomers

1. Physical state C1 C3 gases
C4 C20 liquids
> C20 : solids
2. Dipolemoment (!) cis > trans
3. Polarity cis > trans (for Cab=Cab type of alkenes)
4. Melting point increases with M.W. trans > cis
(due to more packing capacity)
5. Boiling point increases with M.W. cis > trans
# branching decreases B.P.

<CC=CC
Polarity increases, boiling point
increases
6. Solubility Practically insoluble cis > trans
in water but fairly Polarity increases, solubility in polar
soluble in nonpolar solvents increases.
solvents like benzene
petroleum ether, etc.
7. Stability trans > cis
(cis isomers has more VanderWaals
repulsion)

TABLE-2 COMPARATIVE STUDY OF ALKANES ALKENES ALKYNES

Properties Alkanes Alkenes Alkynes

1. Bond length 1.54 (C C) 1.32 (C = C) 1.20 (C " C)

2. Bond energy(KJmol-1) 415 (C C) 615 (C = C) 835 (C " C)

3 2
3. Hybridization sp sp sp

4. % s character 25% 33% 50%

5. pKa 50 44 25

6. Electronegativity of C sp3 (C) < sp2 (C) < sp (C)

7. Polarity R CH2 CH3 R CH = CH2 R C" C

8. Rate of hydrogenation less more

9. Rate of electrophilic
addition reaction more less

10. Heat of combustion C2H6 ( 373) C2H4 ( 337 kcal) C2H2 ( 317 kcal)

3
11. Density (g/cm ) C3H8 (0.50) C3H6 (0.52) C3H4 (0.67)

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