Part 7: 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 schematic of the solution is shown below. The information from the question is given in black. Deductions directly from this information are given in red. Points that provide potential key information are shown in green which leads to the structures. The logical thougth pathway is to identify H first, then deduce A / D then C / E to then confirm the stereochem of A and D. A and D then give B. F and G are a separate sub group that are closely related to each, the key steps being that F is an isomer of A, a cycloalkane with only one H type.
There are, of course, other possible thought pathways.

Common mistakes:

• Incorrect stereochemistry of A and D.
• F would have given several monochlorination products.

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