The final product of this sequence, D, is an orange, crystalline solid melting at 174(C and having molecular weight 186:

In its 1H and 13C NMR spectra, product D shows only one kind of hydrogen and only one kind of carbon, respectively.
Draw the structure of C and make a structural suggestion as to how the high degree of symmetry of D can be explained. (D belongs to a group of compounds named after something you might get at a deli for lunch.)

Transcribed Image Text:

Cyclopentadiene Na C+ H2