14. Synthetic Techniques

Fill in each box with the appropriate reagent:

c.

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(a) trans-cyclopentane-1,2-diol

Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)

(h)

Starting with cyclohexene, how can the following compounds be prepared?

a. methoxycyclohexane

Propose mechanisms to explain the opposite regiochemistry observed in the following two reactions.

What reagents should be used to carry out the following syntheses?

Identify A–E.

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

b.

Which of the reactions cannot be used for the synthesis of isobutyl alcohol?

Write the appropriate reagent over each arrow.

Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal number of steps is indicated over the reaction arrow, although there may be alternate routes worth considering.

(a)

How could the following compounds be prepared, using cyclohexene as a starting material?

a.

Show how you would accomplish the following synthetic transformations. Show all intermediates.

d. trans-hex-2-ene → hex-2-yne

Starting with cyclohexene, how can the following compounds be prepared?

c. dicyclohexyl ether

Give the structures of the intermediates represented by letters J, L, M, and N in this synthesis.