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 syntheses efficiently (you may use any necessary reagents).

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

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.

(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.

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(d) butan-2-ol → 2-methylbutanoic acid