Question

Given the following chlorides: 1-chlorobutane, 2-chlorobutane, t-chlorobutane, benzyl chloride, and chlorobenzene.

Arrange the chlorides tested in order of decreasing experimental reactivity toward silver ion. Consider just the aliphatic compounds and ignore the aromatic ones. What structural change correlates with reactivity? Assuming this to be a SN1 reaction, and the reaction is faster for more stable cation intermediates, indicate the order of stability of all the carbon cations formed from each alkyl halide. Examine the cations and explain what makes some cations more stable than others. (Hint: Draw their structures)

Answer 1