[miskie85]

I need to identify a number of lettered unknowns by following the chemical reactions.

And here is the problem.

An organic compound A. C₁₅H₁₆O₂ did not react with 2,4-dinitrophenylhydrazine.

Compound A. C₁₅H₁₆O₂ react with excess acetic anhydride to give compound B. C₁₉H₂₀O₄.

Compound A react with potassium dichromate in sulfuric acid gave compound C. C₁₅H₁₂O₄.

Strong heating of compound C gave compound D. C₁₄H₁₂O₂

Compound D was slowly soluble in sodium bicarbonate solution, and when heated with bromine and a trace of PCl₃ gave only

compound E. C₁₄H₁₁BrO₂, which was not susceptible to further bromination by this method.


I think compound A should be carboxylic acid or esters. However, can carboxylic acid or ester react with acetic anhydride ?

And, can carboxylic acid oxidized with potassium dichromate in sulfuric acid?

[Dan]

I think compound A should be carboxylic acid or esters.

Why?

[orgopete]

When A reacted with Ac2O, how many acyl groups were added?

Describe the functional groups that must have been present in A?