Introduction Alkyne

R1–CC–R2
Alkynes have SP carbon, therefore it is electronegative (% S = 50 %)
Conversion of Lower Alkyne to Higher Alkyne
R–CC–H ⎯→ R–CC–CH3
Due to acidic Hydrogen, the alkynes react
+ –
The Acidic Hydrogen react with Base. Na NH2
+ – Θ
Sab – aur + ka R–CC–H + Na NH2 ⎯→ R–CC : + NH3
chakkar hai This will behave like
babu bhaiya a Grignard reagent,
Θ
R–CC : + CH3Cl ⎯→ R–CC–CH3 + Cl–
Methods of Preparation Alkyne
There are 3 methods of preparation of Alkynes in your syllabus :
1. Using Calcium Carbide
2. Using CHI3
3. Using Vicinal Dihalide
 Methods of Preparation Alkyne
Alkynes using CaC2 + 2H2O ⎯→ H–CC–H + Ca(OH)2
Calcium Carbide
Θ Θ
: CC :
 Methods of Preparation Alkyne
Alkynes using
CHI3
CHI3 ⎯⎯ →
3Ag
Powder
HCCH + 3AgI
I
| I
1 CH –
+ e ⎯→ CH•
I I I
I I I I
I | | | |
2 2•CH ⎯→ H—C• + •C—H ⎯→ H—C—C—H
I | | | |
I I I I

Dehalogenation 3 H—C=C—H
| |
I I

Dehalogenation 4 H-CC-H
 Methods of Preparation Alkyne
Alkynes using H H
CH3 H
⎯⎯⎯→ CH3–CC–CH3
| | alc KOH NaNH2 /
Vicinal dihalides CH3—C—C—CH3  3 C=C
| | Br CH3
Br Br 3

Dehydrohalogenation Dehydrohalogenation
Acidic Nature Chemical Properties of Alkynes
 Θ
R–CC–H + Na NH2 ⎯→ NH3 + R–CCΘ Na

R–CC–H + CH3MgBr
Θ 
⎯→ CH4 + R–CCΘ MgBr

R–CC–H + KOH ⎯→ H2O + R–CCΘ: K

Above 2 reaction will take place but the third reaction will not take place
Strong Acid → Weak Acid reaction is feasible
 2nd Property : Chemical Properties of Alkynes
Electrophilic Addition
Alkynes undergo electrophilic Addition
H–Cl
R1–CC–R2
H+
1 R1–CC–R2 ⎯⎯
→ R1—C=C—R
| 
2 H+ attack will take place.
H
Cl
ClΘ |
2 R1—C=C—R2 R —C=C—R Cl- attack will take place.
|  1
|
2
H H Cl Cl
| H+ |
3 Again H+ attack will take place. R1—C=C—R2 ⎯⎯ → R1—CH—C—R

2
| |
H H
Cl Cl
| ClΘ |
R1—CH2—C—R2 R1—CH2—C—R2
 |
Cl
3rd Property : Chemical Properties of Alkynes
Ozonolysis
(1) O3
R1–CC–R2 R1—C—C—R2
(2) Zn/H2O || ||
O O
4th Property : Chemical Properties of Alkynes
Isomerization
1 Alkyne can be converted to 2 alkyne on reaction with alc KOH and NaNH2
alc KOH
R1–CH2–CCH R1–CC–CH3
Na NH2

R1–CH2–CCH alc KOH

R1–CH2–CCΘ : + H2O

R1–CH2–CCH R1–CC–CH3
Alpha H =2 Alpha H =3

R1–CH2–CCH NaNH2 R1–CH2–CCΘ : + NH3

 Chemical Properties of Alkynes

Red Hot
HCCH Cu

Red Hot
CH3–CCH
Cu
vishal_vtsir