Question

Explain what is the difference between the experiments synthesis of tert-butyl chloride and the synthesis of butyl chloride in terms of: 1) Process, 2). Reaction mechanism

Answer 1

Solution:

Difference between the synthesis of tert-butyl chloride and butyl chloride is given in the below table.

tert-butyl chloride	Butyl chloride
1) Process:
- Reactants are tert-butanol, concentrated aqueous HCl.	- Reactants are n-butanol, concentrated aqueous HCl, ZnCl2. ZnCl2 acts a dehydrating agent
- Ambient temperature reaction.	- Reflux temperature reaction.
- Reaction shall be carried out in separatory funnel. (Inside the fume hood)	- Reaction should be carried out in a reaction set up with reflux condenser. (Inside the fume hood)
- Faster conversion.	- Slower conversion
- Purification of the product is by slower fractional distillation.	- Purification of the product is by slower fractional distillation (Multiple times).
- Typical yield is 40 - 60% on tert-butanol.	- Typical yield is 60 - 70% on n-butanol.
2) Mechanism:
- Reaction proceeds through SN1 pathway. (Mechanism is given below in the below image)	- Reaction proceeds through SN2 pathway. (Mechanism is given below in the below image)