Question

identify compounds A-E based on the information in order to receive full credit: given. Please note that you must show all of your reasoning Compound A had the molecular formula CtHa Its proton NMR is shown below. Reaction of A bromosuccinimide, and subsequent workup, produced with N- one product, compound B. but one was Compound C had the molecular formula CaH,o2: Its proton NMR consisted of only two signals extremely downfield (around 10ppm). Also, its IR included a very strong signal at-17vodcm reacted very readily with compound A at slightly elevated temperatures to produce a singe D. Compound D's formula was CoHioo2 . Compound C t compound product, co E. Compound D was able to react with two equivalents of methylmagnesium bromide to produce compound Compound E's IR spectrum most notably included a very strong, broad band at around readily untiact well with various oxidizing agents, it did not undergo substitution or elimination readily until it was treated with reagents such as PBr 0 9 87 6 5 4 3 2 0 bom

Answer 1