Organic Chemistry Laboratory I - Chem 341

Quiz 7a

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 an aromatic C-H bond. (1 pt)

Aromatic C-H stretches show up just above 3000 cm^-1, usually around 3050 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: chemical shift. (2 pts)

Variations in the NMR frequencies of the same kind of nucleus (H¹) are due to variations in the electron density around that nucleus; these are called the chemical shifts. Chemical shifts depend on the electronegativity of the nearby atoms and the hybridization of adjacent atoms.

In a H¹ NMR the chemical shifts of protons usually vary from 0 to 12 ppm.

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

(a) How many different types of protons (i.e. how many unique signals) will appear in the spectrum? (1 pt)

Five