Question

3. When 1,4-dimethylcylopent-1-ene is treated with chlorine in water, a racemic mixture of one of the depicted constitutional isomers is formed. Circle the correct product and write the steps in the mechanism that show how this reaction occurs. Be sure to show the following: (1) all necessary curved arrows (2) the structure of any intermediates that are formed during the mechanism, including stereochemistry (3), what, If anything. Is added or lost during each step of the mechanism, (4) any nonzero formal charges. REMEMBER: You may not use any materials except those that are given in the equation, 1,4-dimethylcyclopent-1-ene Cl2/11,0

Answer 1

When an alkene reacts with halogen (X₂ ) then the reaction proceeds via cyclic intermediate. It is due to the formation of cyclic intermediate the product should be anti in nature.

The detail reaction mechanism and the product formation is shown below.

product . :02: (1,4-dimethyl cyclopental-ene) e eyclic Cintermediate). Between uo and H2o the uncleophiliuty of 420 is higher than that of a thus in the cyclic intermediate. Ho attacks as mucheophile to from the final product the nucleophile , Ho, attocks from the less sulsstituted side to avoid the storie hindarence hindrance. I less hindrance side Most hindrance Side. Ho ( final product).