09-218 Organic Chemistry II: Advanced Problem Set #2 Covers Lectures 6-9

1. Which of the following are aromatic compounds?

2. Reaction of the furan derivative shown below with bromine and FeBr3 yields a mixture of two monobromination products.

A. Write structures for the two products in the boxes above. B. Use resonance forms to predict the major and minor products.

3. Fill in the correct structure or circle the appropriate compound.

O N2H4 KOH

4. Complete the following synthesis starting from benzene and any other necessary reagents.

5. Based on the spectral data provided below, propose the structure C8H11NO IR = 1720 cm-1
1

H-NMR 7.3 (d, 2H) 6.5 (d, 2H) 4.4 (s, 2H) 2.5 (q, 2H) 1.0 (t, 3H)