Lec: 1 Hydro-Carbon

Vishal Vivek Tiwari

Chemistry Faculty
Career Point Kota
 Recap…..
➢ Birch Reduction – To make Trans Alkene
➢ Birch Reduction of Benzene ⎯⎯⎯→
Na
NH 3

➢ Alkane form Alkyl Halide

➢ Wurtz Reaction 1. Na
R–X → R–R
2. Dry Ether
 Wurtz Reaction
Find the product formed in the following ques. of Wurtz reaction :

CH3–Cl ⎯⎯⎯⎯Na
→
Dry ether
Mechanism
Na → Na+ + e– R–X → X + R 
CH3 + e– → CH3
.
6e– (7e–)
. .
CH 3 + CH3 → CH3 – CH3
 Wurtz Reaction
Find the product formed in the following ques. of Wurtz reaction :
C2H5Br ⎯⎯⎯⎯Na
→ C4H10 + 2 NaBr
Dry ether

Imp points C2H5● + C2H5●

Free radical show disprop Reaction(same species show oxidation & reduction)
C2H4 (ethane)
● ● Disprop.
C2H5 + C2H5
H C2H6 (ethene)
Along with Butane ethane & ethene also gets produced
✓ Butane is Major Product
✓ Ethane & Ethene are Minor Product
Super Practice Question Wurtz Reaction
Which product is not possible in the following reaction :

C2H5 Br ⎯⎯⎯⎯
Na
→
Dry ether

(A) CH3–CH2–CH2– CH3

(B) CH3–CH2– CH3
(C) CH3– CH3
(D) CH2=CH2
Super Practice Question Wurtz Reaction
Find the product in the following Wurtz reaction

CH3–Cl + 2Na + Cl–C2H5 ⎯⎯⎯⎯→

dry ether CH3–CH2–CH3
Propane (not good yield)
Products formed in the reaction
CH3–CH2–CH3 Propane
C2H 6 Ethane
C4H10 Butane
Wurtz reaction is good for molecules having even number of carbon
Super Practice Question Wurtz Reaction
Which of the following compounds will give good yield in Wurtz reaction :

a) CH4
b) CH3–CH3
c) CH3–CH2–CH3
d) CH3–CH2–CH2–CH3
e) CH3–CH2–CH2–CH2–CH3

Wurtz reaction is good for molecules having even number of carbon

& symmetric molecules
Super Practice Question Wurtz Reaction
Which of the following compounds will give good yield in Wurtz reaction :

(even + unsymmetrical)
not good yield

(even + unsymmetrical)
not good yield

(even + symmetry)

Super Practice Question Wurtz Reaction
Which of the following compounds will give good yield in Wurtz reaction :

(even + symmetry)


(even + unsymmetrical)
not good yield
Super Practice Question Wurtz Reaction
Find the product in following Wurtz reaction :

Cl
Cl ⎯⎯⎯⎯Na
→ ● ●
Dry ether

⎯⎯⎯⎯ →
Na
(2)
(1) Cl + dry ether
Cl
Super Practice Question Wurtz Reaction
Find the product in following Wurtz reaction :
Cl

⎯⎯⎯⎯ →
Na
(3)
(1) dry ether
Exactly same as Wurtz Frank-land Reaction

CH3 – Cl + Zn + Cl – CH3 dry ether CH3 – CH3

➢ Frank-land reaction is exactly same as Wurtz reaction

➢ In place of Na , we have to use Zn
➢ Don’t use 2 mole of Zn here because Zn releases 2 atoms
➢ Even Carbon & Symmetric Molecule has good yield
Super Practice Question Frank-land Reaction
Find the product in the following reaction

CH3 – Cl + Zn + Cl – C2H5 ⎯⎯⎯⎯→

dry ether
 Fittig Reaction
Fittig reaction = Cyclic halide → Cyclo- Alkane
Fittig reaction = Benzene halide → Cyclo - Alkane
➢ Wurtz reaction deals with Aliphatic Halides
➢ Fittig reaction deals with Aryl Halides
 Wurtz - Fittig Reaction
When both aryl halide and aliphatic halides are mixed then, reaction is called
Wurtz Fittig reaction
Method 2 Reduction of Alkyl Halides
Directly Alkyl Halides can be converted to alkanes by reduction using :
1. Zn + dil HCl Zn + CH3COOH Zn/Cu +C2H5OH
2. Li AlH4
3. Na BH4
4. Ph3 Sn H
5. HI/red P
 Reduction of Alkyl Halides
Reduction using (a) Zn + dil HCl (b) Zn + CH3COOH (C) Zn/Cu +C2H5OH
Zn + dil HCl
CH3 – Cl
Mechanism :
 Reduction of Alkyl Halides
Reduction using Li AlH4 Na BH4 Ph3 Sn H

CH3 – Cl
Mechanism :
 Reduction of Alkyl Halides
Reduction using Li AlH4 Na BH4 Ph3 Sn H

Ph3 SnH Reduces all 1,2,3 degree alkyl halides

Li AlH4 Reduces all 1,2 degree alkyl halides
Na BH4 Reduces only 3 degree alkyl halides
vishal_vtsir