Part 9 : STRUCTURE DETERMINATION

Note that these types of questions are often the most difficult on the examination. This is because they are holistic in that they require a good understanding of the reactions and the concepts and the ability to apply those concepts. They can't be memorised, they require understanding and ability to apply. Hence they help discriminate those who truly understand from those who have memorised and will soon forget.

A full schematic of the full solution is not available at this time.

Key information is for A .... C9H12 IHD = 4, CNMR data suggests aromatic with 2 types of sp3 C this gives isopropylbenzene as the starting point. Radical bromination at the benzlic position gives B followed by elimination to a sinlge possible product C. Allylic radical substitution gives D. Nucleophilic substitution (SN2) of D provides E which is reduced to F. SN2 of F gives G.