Conversion Reactions (II) Problem 4

Description:

Problem

What reactions will bring about the following conversions?

1. Propene to Propyne

2. Propene to 1 - nitropropane

Solution

1. Propene to Propyne

• By reacting propene with Br₂/CCl₄, vicinal dibromide is obtained which undergoes elimination reaction in the presence of EtOH and heating to give propyne.

2. Propene to 1 - nitropropane

• The product has nitro group attached to C1 carbon atom.

• Thus, we react the given alkene with HBr in the presence of peroxide to get Antimarkovnikov’s product where bromine is attached to carbon atom with more number of hydrogen atom (C1).

• The bromine is now replaced with NO₂ by reacting it with AgNO₂ in the presence of EtOH − H₂O.