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 presented below. This is also presented in several parts, where each diagram has more information added to it.
The idea behind this is to encourage students to see how to work towards the answer by building up the answer from the information in the question gradually.

Diagram 2 gives the basic information from the question in black and deductions directly from this information are indicated by red arrows and with blue text plus it identifies the functional groups and points that provide potential key information by green arrows and key initial structures.

Diagram 3 gives the completed solution with the structures in blue. In this problem the are several routes to connect the structures.  
Key  steps are recognising the methylcyclopentane framework (based on the name) and the carbocation rearrangements to the cyclohexane systems.