Question

(a) give all reactions that you can think of which would result in termination of the chain reaction of a free radical halogenation. (b) Assuming that the hydrocarbon being chlorinated is neopentane and that the propagation steps in the mechanism each take place 100 times for each termination step, what is the expected weight ratio of neopentyl chloride to neopentanesulfonyl chloride in the final crude reaction product? show work. (c) write the structures of the two monochlorinated products that could result form the chlorination of 2,3-dimethylbutane. how many dichloroalkanes can result? draw all of them (d) if the reaction mixture containing hte chloro products of 3-methylpentane is shaken with aqueous silber nitrate solution and the s=resulting organic layer is then injected into the gas chromatograph, one of the monochlorinated product peaks is now much smaller than is was in the original product mixture. explain.

Answer 1

Free radical halogenation

(a) termination steps are shown below

(b) For neopentyl system, the expected weigth ratio for neopentyl chloride to neopentylsulfonyl chloride would be 100/1 times.

(c) Drawn below are the monochlorinated products

We would form 3 dichlorinated products. Structures are shown below

(d) The tertiary chlorinated product formed from 3-methylpentane reacts with added AgNO3 and thus the concentration of this decreases which is clearly seen from the GC chart. the other two products primary and secondary chlorinated products are more stable and less likely to loose its chloro group.