Practice Problem

Compound A (C7H16O, spectra 1 & 4) reacts with H2SO4 to form B. [note: for a review of Degree of Unsaturation go here.] Ozonolysis of B followed by dimethyl sulfide reduction produces C (spectrum 2) and D (spectrum 3). What are the structures of A-D? How do I solve this problem? Try to solve it without help but if you are in dire need, try here if you dare.

Spectrum 1


Spectrum 2

Spectrum 3


Spectrum 4