Organic Chemistry Laboratory I - Chem 341

Quiz 7c

1. Calculate the oxidation state of the labeled carbon atom and determine whether this reaction is an oxidation, a reduction, or neither. (2 Pts)

2. Propose a stepwise arrow pushing mechanism for the following organic reaction. (3 Pts)

3. In the functional group region of the IR spectrum, estimate the absorption region associated with a carbon-oxygen double bond. (1 pt)

Carbonyls show up from 1800 – 1650, with most centered around 1700 cm^-1.

4. Circle the compound that is most consistent with the following FT-IR spectrum. (1 pt)

5. Define or give an example to explain the following NMR term: upfield shift. (2 pts)

The upfield region of the 1H NMR spectrum is towards zero. Protons that are surrounded by electron donating groups are upfield relative to protons near electron withdrawing groups, which are downfield.

6. Consider the compound below and answer the following questions regarding the ¹H NMR spectrum for that compound.

(b) What would the splitting pattern look like for the protons on the labeled carbon (e.g. singlet, doublet, triplet, etc.)? (1 pt)

The methyl group adjacent to the carbonyl has no adjacent protons. Therefore, n = 0 and n + 1 = 1. So it will show up as a singlet.