16. Conjugated Systems

The ψ₂ molecular orbital for octa-1,3,5,7-tetraene is shown. Draw ψ₃.

<IMAGE>

Hexa-1,3,5-triene uses six p orbitals, each containing a single electron, to make its three π bonds. How many total molecular orbitals are made by the six p orbitals?

Identify the isoprene units in the terpenes shown. In cross-linked or ring-containing terpenes, linkages can be formed between more than just C₁ and C₄ of isoprene.

(b)

Identify the isoprene units in the terpenes shown. In cross-linked or ring-containing terpenes, linkages can be formed between more than just C₁ and C₄ of isoprene.

(c)

Identify the isoprene units in the terpenes shown. In cross-linked or ring-containing terpenes, linkages can be formed between more than just C₁ and C₄ of isoprene.

(e)

Vitamin E, especially the B ring and the side chain, is a terpenoid derivative. Identify the isoprene units nature used to make it.

For the following terpenes, identify the isoprene units. In cross-linked or ring-containing terpenes, linkages can be formed between more than just C₁ and C₄ of isoprene.

(a)

For the following terpenes, identify the isoprene units. In cross-linked or ring-containing terpenes, linkages can be formed between more than just C₁ and C₄ of isoprene.

(d)

North American termite soldiers, when encountering enemy insects, contract their mandibular muscles, expelling a mixture of chemicals that essentially trap their enemies in a glue-like substance. This weapon, built into the face of the termite, is called the fontanellar gun. It releases a mixture of pinene (62%), myrcene (27%), and limonene (11%).

(b) Suggest an acid-catalyzed mechanism by which pinene could be produced from limonene.

Identify the following dienes as being in the s-cis or s-trans conformation. If they are in the s-trans conformation, draw them in the s-cis conformation. [It may not always be possible.]

(c)

Identify the following dienes as being in the s-cis or s-trans conformation. If they are in the s-trans conformation, draw them in the s-cis conformation. [It may not always be possible.]

(e)

At pH = 7, one of the ions shown here is purple and the other is blue. Which is which?

Determine whether each structure is likely to be colored or not. For those that you predict to be colored, indicate the extended conjugation by marking the series of continuous sp² hybridized atoms.

(a)

(b)

(c)

Determine whether each structure is likely to be colored or not. For those that you predict to be colored, indicate the extended conjugation by marking the series of continuous sp² hybridized atoms.

(d)

(e)

(f)

How can you use UV spectroscopy to distinguish between the compounds in each of the following pairs?

c.