A graduate student was following a procedure to make 3-propylcyclohexa-1,4-diene. He overheated the product. He isolated the product, which gave the appropriate =C−H stretch in the IR, but the C=C stretch appeared around 1630 cm−1as opposed to the literature value of 1650 cm−1for the desired product. The mass spectrum showed the correct molecular weight, but the base peak was at M–29 rather than at M–43 as expected. Because of the anomalous IR spectrum, he took a UV spectrum that showed λmaxat 261 nm. c) Draw the structure of the desired product and propose a structure for the actual product d) Show why he expected the MS base peak to be at M–43, and show how your proposed structure would give an intense peak at M–2
A graduate student was following a procedure to make 3-propylcyclohexa-1,4-diene. He overheated the product. He isolated the product, which gave the appropriate =C−H stretch in the IR, but the C=C stretch appeared around 1630 cm−1as opposed to the literature value of 1650 cm−1for the desired product. The mass spectrum showed the correct molecular weight, but the base peak was at M–29 rather than at M–43 as expected. Because of the anomalous IR spectrum, he took a UV spectrum that showed λmaxat 261 nm.
c) Draw the structure of the desired product and propose a structure for the actual product
d) Show why he expected the MS base peak to be at M–43, and show how your proposed structure would give an intense peak at M–2
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 1 images
