Question

Draw the structure with the molecular formula C6H14O that most likely produced the below IR and 1H NMR. The 13C NMR data is 78.3 ppm, 43.9 ppm, 27.3 ppm, 13.3 ppm.

Answer 1

Answer:

                   The answer is 2,3-dimethylbutan-2-ol and the structure is attached below.

Explanation:

                     Although we are not provided with ¹H-NMR spectrum and IR spectrum but still we can elucidate the ¹³C-NMR data and finalize a plausible structure.

                      First of all we look at the molecular formula, we can conclude from the formula that the structure given is saturated in nature because the hydrogen deficiency index of this formula is zero. Hence, we can say that there is no double bond either between Carbon atoms or between carbon and oxygen atom. This can also be proved by the absence of peaks in downfield as unsaturated compounds and carbonyl compounds give value above 100 and 200 ppm respectively.

                      Secondly, we can also conclude that among the six carbon atom two pairs of them are having same electronic environment because we are having only 4 signals hence we can conclude that two pairs have same chemical shift values.

                       Also, after making every possinble isomer of given molecular formula the structure of 2,3-dimethylbutan-2-ol was found to be the most accurate structure.