Reference no: EM132319754

Problem set 1:

The NMR spectra of an organic compound of molecular formula C₁₁H₁₀O₃ was recorded on 400 MHz instrument. Elucidate the structure based on the NMR spectra provided. NMR spectra provided includes 1H, 13C, DEPT 135, DEPT 90, COSY and HSQC (attachment 1: Problem set 1). COSY and HSQC are provided ONLY as additional help for the assignment, inclusion in the discussion is NOT compulsory.

In your answer include:

i) 1H spectral details (Chemical shift values, Coupling pattern and constants with unit, Number of proton integration and assignment of peaks as aromatic/alkene/...etc any other remarks)

ii) 13C spectral details (Chemical shift values, type [C, CH₂, CH₃] and assignment of peaks as aromatic/alkene/...etc).

iii) Draw the proposed structure and assign 1H and 13C chemical shift values with brief justification.

Problem set 2:

In this problem you have to elucidate the structure of product B. A substrate A (structure shown in scheme 1) which was subjected to two consecutive reactions as shown in scheme 1 below to give the product B of molecular formula C₉H₁₄Br₂. Provide the structure for Product B based on the NMR data provided (attachment 2: Problem set 2). (The 1H NMR and 13C NMR of starting substrate A has been provided for reference purpose only).

The spectra for product B was recorded on 400 MHz instrument. Elucidate the structure based on the NMR spectra provided: 1H, 13C, DEPT 135, DEPT 90.
In your answer include:

i) 1H spectral details (Chemical shift values, Coupling pattern and constants with unit, Number of proton integration and assignment of peaks as aromatic/alkene/...etc and any other remarks)

ii) 13C spectral details (Chemical shift values, type [C, CH2, CH3] and assignment).

iii) Draw the proposed structure and assign 1H and 13C chemical shift values with brief justification.