Problem 8

Compound A, C₄H₈O, reacts with a solution of iodine in sodium hydroxide to give B, C₃H₅O₂Na, and CHI₃. A gives a precipitate with 2,4-dinitrophenylhydrazine but no reaction with ammoniacal silver nitrate.

A can be reduced with lithium aluminium hydride in dry ether to give C, C₄H₁₀O, which is chiral. With sodium chloride in 50% sulphuric acid C gives D, C₄H₉Cl. With magnesium in dry ether D gives G, C₄H₉MgCl; G will react with solid carbon dioxide to give an intermediate which when treated with dilute hydrochloric acid gives H, C₅H₁₀O₂.

If D is heated with potassium hydroxide dissolved in ethanol, three compounds are formed; E is the major product and has two stereoisomers, and F is the minor product. Both varieties of E, and F, are C₄H₈.

C reacts with H in the presence of sulphuric acid catalyst to give I, C₉H₁₈O₂.