) A graduate student was following a procedure to make 3-propyl-1,4-cyclohexadie
ID: 890474 • Letter: #
Question
) A graduate student was following a procedure to make 3-propyl-1,4-cyclohexadiene. During the workup procedure, his research advisor called him into her office. By the time he returned to his bench, the product had warmed to a higher temperature than recommended. He isolated the product, which gave the appropriate C(sp2)-H stretch in the IR, but the C=C stretch appeared around 1630 cm1 as opposed to the literature value of 1650 cm1 for the desired product. The mass spectrum showed the correct molecular weight, but the base peak was M – 29 rather than at M – 43 as expected.
Draw the structure of the actual compound isolated by the student.
Explanation / Answer
The isolated compound would be the ethyl group with the base peak of 29 and the base peak of the propyl group is 43.
The C-H strectch would be in the aromatic compound and C=C stretching frequency is around 1630.
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