22. Carboxylic Acid Derivatives: NAS

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(a) trans-1-bromobut-2-ene → trans-pent-3-enoic acid (two ways)

Determine the major product for the following reaction.

Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two carbons, indicate how the following syntheses could be carried out:

b.

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

c.

Show how each of the following compounds can be prepared, using the given starting material:

f.

What are the products of the following reactions?

i.

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(b)

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

(a) hept-6-en-1-ol → ε-caprolactone

(b) methoxybenzene → p-methoxybenzamide

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(c)

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(d)

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(a) PhCH₂CH₂OH → PhCH₂CH₂COOH

When a chemist attempted the following reaction sequence, the desired product was not formed.

(a) Why?

(b) Suggest a solution to the problem. [Think about chemistry from the end of Chapter 13.]

Using bromocyclohexane as a starting material, how could you synthesize the following compounds?

c.