15. Analytical Techniques:IR, NMR, Mass Spect
Carbon NMR
15. Analytical Techniques:IR, NMR, Mass Spect Carbon NMR
36PRACTICE PROBLEM
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:
(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.
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:
(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.