Q8(e). Identify A (C₁₀H₁₆O) and B from tests and ozonolysis
An unknown compound A, C₁₀H₁₆O, adds 2 moles of bromine to give a tetrabromo derivative. It also forms a hydrazone, reduces Fehling's solution and absorbs in the UV. A undergoes a retro-aldol reaction with boiling aqueous K₂CO₃ to give acetaldehyde and compound B. B gives a positive haloform test and yields acetone and 4-oxopentanoic acid on oxidative ozonolysis. Identify A and B and rationalize your answer.
Model answer
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Coverscitralretro-aldolhaloform testozonolysis
All parts of Question 8
- 8(a) Increasing stability of carbocations5 marks
- 8(b) Identify the antiaromatic compound5 marks
- 8(c) Reagents for an alkyne-to-alkene transformation5 marks
- 8(d) pKa order of four carbonyl compounds5 marks
- 8(e) Identify A (C₁₀H₁₆O) and B from tests and ozonolysis10 marks