Orgoreview

Two alkenes, A and B, have the same molecular formula C₅H₁₀, give the same alkane when treated with H₂/Pd and the same alcohol when treated with H^⊕/H₂O. However, they give different alcohols when treated with BH₃: THF followed by H₂O₂/^ΘOH. Treatment of alkene A with O₃ followed by Zn/H₂O gave two carbonyl compounds C (C₃H₆O) and D (C₂H₄O) that showed the following NMR data. 

C δ 2.07 singlet

D δ 9.79 quartet (1H) and δ 2.21 doublet

Give structures for A, B, C and D