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9

You need to know the terms "staggered" and "eclipsed", because that's what we call these two conformations. Now to the point: the real ethane molecule rotates and changes shape all the time, so both geometries are possible, albeit the top one is more likely, because it is the energy minimum. To make the molecule stop in the staggered ...

2

Compare the quartet at $\pu{4.2ppm}$ and the singlet at $\pu{3.5ppm}$. These quite obviously would, in your friend’s structure, correspond to the protons on either side of the ether-oxygen. However, we should expect the methylene singlet to be more deshielded than the ethyl group’s methylene: It is squashed between an electron-withdrawing $\ce{OR}$ and an ...

4

In IR, wavenumbers below 1500/cm are called the "fingerprint" region. It's very tricky to assign anything there, because the transitions don't relate to specific bonds, but come from larger structures. If you look deeper into the literature, you will surely find an explanation for that big hump at 800something inverse centimeters. Generally, two ...

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