Orgoreview

Propose structures for the lettered compounds based upon the data given below.

 

An alkane A (C₆H₁₄) reacts with chlorine to yield only three compounds (B, C, and D) with the formula C₆H₁₃Cl.  Of these only C and D undergo dehydrohalogenation with sodium ethoxide in ethanol to produce an alkene.  Moreover, C and D yield the same alkene E (C₆H₁₂).  Treating E with HCl produces a compound F that is isomeric with B, C, and D.