91Ó°ÊÓ

The relative energy levels of the five molecular orbitals of the cyclopentadienyl system are similar to those in benzene. That is, there is a single lowest energy MO, above which the orbitals come in degenerate pairs. Draw a diagram like that in Figure 15-5, and tell which of the five orbitals are occupied in the cation, radical, and anion.

Draw structures corresponding to the following names:

(a) 3-Methyl-1,2-benzenediamine

(b) 1,3,5-Benzenetriol

(c) 3-Methyl-2-phenylhexane

(d) o-Aminobenzoic acid

(e) m-Bromophenol

(f) 2,4,6-Trinitrophenol (picric acid)

Draw structures corresponding to the following names:

(a) 3-Methyl-1,2-benzenediamine

(b) 1,3,5-Benzenetriol

(c) 3-Methyl-2-phenylhexane

(d) o-Aminobenzoic acid

(e) m-Bromophenol

(f) 2,4,6-Trinitrophenol (picric acid)

Draw structures corresponding to the following names:

(a) 3-Methyl-1,2-benzenediamine

(b) 1,3,5-Benzenetriol

(c) 3-Methyl-2-phenylhexane

(d) o-Aminobenzoic acid

(e) m-Bromophenol

(f) 2,4,6-Trinitrophenol (picric acid)

Draw structures corresponding to the following names:

(a) 3-Methyl-1,2-benzenediamine

(b) 1,3,5-Benzenetriol

(c) 3-Methyl-2-phenylhexane

(d) o-Aminobenzoic acid

(e) m-Bromophenol

(f) 2,4,6-Trinitrophenol (picric acid)

The following molecular model is that of a carbocation. Draw two resonance structures for the carbocation, indicating the positions of the double bonds.

Azulene, an isomer of naphthalene, has a remarkably large dipole moment for a hydrocarbon ($\mathbf{μ}\mathbf{=}$5 1.0 D). Explain, using resonance structures.

Draw structures corresponding to the following names:

(a) 3-Methyl-1,2-benzenediamine

(b) 1,3,5-Benzenetriol

(c) 3-Methyl-2-phenylhexane

(d) o-Aminobenzoic acid

(e) m-Bromophenol

(f) 2,4,6-Trinitrophenol (picric acid)

Draw structures corresponding to the following names:

(a) 3-Methyl-1,2-benzenediamine

(b) 1,3,5-Benzenetriol

(c) 3-Methyl-2-phenylhexane

(d) o-Aminobenzoic acid

(e) m-Bromophenol

(f) 2,4,6-Trinitrophenol (picric acid)

Draw and name all possible isomers of the following:

1. Dinitrobenzene
2. Bromo dimethyl benzene
3. Trinitrophenol