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:

(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.

13CNMR (CH2)(CH2) C&Hio (CH) 200 180 160 140 120 100 80 60 40 20 0 (ppm)