12. Alcohols, Ethers, Epoxides and Thiols

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.

Show how a protecting group might be used to make these reactions successful.

(b)

Show how a protecting group might be used to make these reactions successful.

(a)