Solution Found!
Two alcohols, A and B, have the same molecular formula C9H10O and react with sulfuric
Chapter 16, Problem 16.49(choose chapter or problem)
Two alcohols, A and B, have the same molecular formula \(\mathrm{C}_{9} \mathrm{H}_{10} \mathrm{O}\) and react with sulfuric acid to give the same hydrocarbon C. Compound A is optically active, and compound B is not. Catalytic hydrogenation of C gives a hydrocarbon D, \(\mathrm{C}_{9} \mathrm{H}_{10}\), which gives two and only two products when nitrated once with \(\mathrm{HNO}_{3}\) in \(\mathrm{H}_{2} \mathrm{SO}_{4}\). Give the structures of A, B, C, and D.
Questions & Answers
QUESTION:
Two alcohols, A and B, have the same molecular formula \(\mathrm{C}_{9} \mathrm{H}_{10} \mathrm{O}\) and react with sulfuric acid to give the same hydrocarbon C. Compound A is optically active, and compound B is not. Catalytic hydrogenation of C gives a hydrocarbon D, \(\mathrm{C}_{9} \mathrm{H}_{10}\), which gives two and only two products when nitrated once with \(\mathrm{HNO}_{3}\) in \(\mathrm{H}_{2} \mathrm{SO}_{4}\). Give the structures of A, B, C, and D.
ANSWER:Step 1 of 3
Based on the given information the structures of the given compounds are as
follows.
\(\mathrm{C}_{9} \mathrm{H}_{10} \mathrm{O}\) out of which the optically active compound A. The two possible structures
as shown below
