Question

Sodium tert-butoxide (NaOC(CH3)3) is classified as bulky and acts as Bronsted Lowry base in the reaction. It is reacted with 2-chlorobutane. Based on this information, the major organic product(s) of this reaction are expected to be _____.

Answer 1

Answer:but-1-ene

Explanation:This is an E2 elimination reaction .

Kindly refer the attachment for complete reaction and products.

Sodium tert-butoxide is a bulky base and hence cannot approach the substrate 2-chlorobutane from the more substituted end and hence major product formed here would not be following zaitsev rule of elimination reaction.

Sodium tert-butoxide would approach from the less hindered side that is through the primary centre and hence would lead to the formation of 1-butene .The major product formed in this reaction would be 1-butene .

As the mechanism of the reaction is E-2 so it will be a concerted mechanism and as sodium tert-butoxide will start abstracting the primary hydrogen through the less hindered side simultaneously chlorine will start leaving. As the steric repulsion in this case is less hence the transition state is relatively stabilised and leads to the formation of a kinetic product 1-butene.

Kinetic product are formed when reactions are dependent upon rate and not on thermodynamical stability.

2-butene is more thermodynamically6 stable as compared to 1-butene  

The major product formed does not follow the zaitsev rule of forming a more substituted alkene as sodium tert-butoxide cannot approach to abstract the secondary proton due to steric hindrance.