[pooky]

Been working for hours on this but find myself moving in circles.

The following reaction sequence was performed: Substance A was reacted with sodium borohydride (in ethanol) and the resulting substance B was then treated with 48% HBr, yielding substance C. This was then reacted with concentrated NaOH in ethanol to give a product D. Analysis of D showed a molecular formula of C8H8. A spot test with deep purple acidic KMnO4 solution on A produced no reaction. A spot test with deep purple acidic KMnO4 solution on B produced a colourless solution with a brown precipitate.
Additionally, a spot test on A with a solution sodium bicarbonate produced no bubbles.

What is the name of compound A?

Any help would be appreciated!

[ooosh]

A  B  reduction
B  C  halogenation
C  D  elimination

[orgopete]

acetophenone?

[pooky]

Thankyou for your replies! I managed to work through and got the answer which was, as orgopete suggested, acetophenone. I have another one that I am equally puzzled with! If anyone is willing to have a crack, here it is:

An unknown compound A gave the following results with spot tests: No gas was produced when NaHCO3 solution was added and the unknown did not dissolve in NaOH solution. Further, no colour change was observed upon treatment with acidic potassium permanganate solution (i.e. it remained a deep purple colour).

Treatment of compound A with an H2SO4/HNO3 and heat gave compound B, which upon careful reaction with sodium borohydride(in ethanol) yielded compound C. When C was reacted with 48% HBr compound D was produced, which upon analysis, showed a molecular formula of C8H8BrNO2. The compound D was also shown to be optically active with one stereogenic carbon.

What is the name of compound A?

[ooosh]

still acetophenone,just an additional nitration make you confused again.

[sjb]

still acetophenone,just an additional nitration make you confused again.

Are you sure? Where's the chirality arrived from here?