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 from the course as a whole. 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 indicated by red arrows. Points that provide potential key information are shown in green which leads to the structures.... In this problem, A can be determined based as a bromide based on the MS data and it's structure from the spectral data. A leads to B, C then D. The functional group tests help identify F and from there the alkyne in E. The named structure reveals the two phenyl groups, and the stereochemistry (meso) of H is used to complete the structures and then there is a series of reactions that can be linked with some spectral data to help along the way. There are, of course, other possible thought pathways.

Common errors:

Ignoring or incorrect stereochemistry of E, could not draw ethylene oxide, did not recognise that A contained Br, counting C atoms, incorrect structure of the ylid D, showing E as an alkene.