12. Alcohols, Ethers, Epoxides and Thiols

Which of the follosing is the best synthesis of the given molecule?

(•) For each of the following reactions, identify the bonds that are broken and formed. Be sure to indicate whether the bond that is broken is a σ bond or a π bond. (c)

(••••) Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.] (a)

(••••) Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.] (b)

(••••) Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.] (c)

Show how you would use a protecting group to convert 4-bromobutan-1-ol to hept-5-yn-1-ol.

Show how each of the following compounds can be prepared from the given starting material. In each case, you will need to use a protecting group. a.

b.

Show how each of the following compounds could be prepared from the given starting material. Each requires a protecting group. a.