a-student-tried-to-synthesize-some-cyclohexyl-chloride-in-the-laboratory-by-reac

Question

A student tried to synthesize some cyclohexyl chloride in the laboratory by reacting cyclohexanol with one equivalent of sodium chloride in a large excess of concentrated sulfuric acid. Unfortunately, the synthesis was not successful, and after the synthesis was completed, the student isolated a compound of formula C₆H₁₀. If the ¹³C-NMR spectrum of the compound is shown below:
13C-NMR spectrum showing peaks for a compound with formula C6H10.

(i) Give a plausible structure for the product.
(ii) Assign all peaks in the ¹³C-NMR spectrum of the product.
(iii) To obtain a higher yield of cyclohexyl chloride, suggest modifications in the reaction.

Accepted Answer

NMR spectrum with peaks at 128 ppm, 25 ppm, and 23 ppm, and modification using PCl3.

Answer

NMR spectrum with peaks at 128 ppm, 25 ppm, and 23 ppm, and modification using Cl2.

Answer

NMR spectrum with peaks at 128 ppm, 25 ppm, and 23 ppm, and modification using Cl2.

Answer

NMR spectrum with peaks at 128 ppm, 25 ppm, and 23 ppm, and modification using HCl.