14. Synthetic Techniques

Fill in each box with the appropriate reagent:

c.

a. Starting with 3-methyl-1-butyne, how can you prepare the following alcohols?

2. 3-methyl-1-butanol

b. In each case, a second alcohol would also be obtained. What alcohol would it be?

Write the appropriate reagent over each arrow.

Using hex-1-ene 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.)

d. hex-2-yne

e. hexan-2-one

f. hexanal

Using hex-1-ene 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.)

g. pentanoic acid

h. pentanal

i. undec-6-yn-5-ol

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

d. trans-hex-2-ene → hex-2-yne

Complete each synthesis by providing the structure of the major product at each step, including any important stereochemistry.

a.

Complete each synthesis by providing the structure of the major product at each step, including any important stereochemistry.

b.

c.

d.

Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than six carbon atoms. You may use any additional reagents you need.

(c)

Propose a synthesis of the carbonyl(s) using the (ii) dihydroxylation/periodic acid cleavage pathways.

(a)

Propose a synthesis of the carbonyl(s) using the (ii) dihydroxylation/periodic acid cleavage pathways.

(b)

Give the structures of the products represented by letters in this synthesis.

Part 2:

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

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.

(c)

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

a.

b.