A laboratory student was converting cyclohexanol to cyclohexyl bromide by using one
Chapter 13, Problem PROBLEM 13-31(choose chapter or problem)
A laboratory student was converting cyclohexanol to cyclohexyl bromide by using one equivalent of sodium bromide in a large excess of concentrated sulfuric acid. The major product she recovered was not cyclohexyl bromide, but a compound of formula C6H10 that gave the following 13C NMR spectrum: 13C NMR 180 160 140 120 (ppm) (CH2) (CH) (CH2) 200 100 80 60 40 20 0 C6H10 (a) Propose a structure for this product. (b) Assign the peaks in the 13C NMR spectrum to the carbon atoms in the structure. (c) Suggest modifications in the reaction to obtain a better yield of cyclohexyl bromide.
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