Mass Spec

There are 3 questions:

Question 1:

On the next two pages are the MS, IR, ¹H and ¹³C NMR, DEPT, COSY, and HETCOR spectra of an unknown compound. The molecular formula is C₈H₁₅BrO₂. Please do the following:

1. Propose a structure for this compound.

2. Assign the ¹H NMR and ¹³C NMR spectra for your proposed structure.

Question 2:

On the following four pages are the IR, ¹H and ¹³C NMR, DEPT, COSY, HMBC and HMQC spectra of an unknown compound. The molecular formula is C₁₁H₂₀O₃ (MW: 200). Please do the following:

1. Propose a structure for the compound.

2. Assign the ¹H NMR and ¹³C NMR spectra for your proposed structure.

Question 3:

On the next several pages are the ¹H, ¹³C, COSY, HMQC, HMBC and ROESY spectra of compound X. The structure of X is shown below.

- Completely assign the chemical shifts on the ¹H NMR and ¹³C NMR spectra of this compound using the numbering system shown below.