Question

Compound A [C6H12] when treated with ozone followed by zinc and water produced methanal and 2,2-dimethylpropanal. Treatment of A with mercuric acetate and water followed by sodium borohydride produced compound B [C6H13OH], which when heated with concentrated sulphuric acid formed compound C [C6H12]. Onzonolysis of compound C gave propanone (aka acetone) as the only product.

Determine the structures of compounds A,B and C and give the steps of the mechanism by which B is converted to C.

Answer 1

OZONE only affect double bonds creating carboxilics.

Answer 2

SIDE NOTE: it is also good in synthesis for breaking benzene into carboxlilcs acids :)

Answer 3

sodium borohydride follows anti markovnikov, so you get a primary alcohol

Answer 4

USING a concentrated acid is often used to remove primary alcohols and create double bonds (dehydration reaction)