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1. In this experiment we used ABCN (1,1’-azobis(cyclohexanenitrile)) as the init

ID: 919368 • Letter: 1

Question

1. In this experiment we used ABCN (1,1’-azobis(cyclohexanenitrile)) as the initiator. There are other initiators that could be used instead such as benzoyl peroxide (shown below). Give a curved arrow mechanism for how the reaction might be initiated with benzoyl peroxide using sulfuryl chloride. Give the three steps of initiation. The reaction is the radical chlorination of 1-chlorobutane with sulfuryl chloride.

2. In lecture you have learned about the free radical halogenation using either chlorine or bromine. You have also learned that bromine is more selective in its reaction than chlorine. Consider the compounds shown below and give the major product ofreaction for each of these compounds with bromine (with hv).

A-

B-   C- 3,5,5-trimethylhexane

3- Rank the compounds in question 2 in order of increasing reactivity toward free radical bromination.

4. Consider compound C from question 3. Give all possible products of freeradical chlorination that are constitutional isomers. Circle the products that would exist asa pair of enantiomers.

Explanation / Answer

1. In this experiment we used ABCN (1,1’-azobis(cyclohexanenitrile)) as the init