14. Synthetic Techniques

Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with the molecule at the left.

(c)

Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.

d. 3-phenylprop-2-en-1-ol

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(e) benzyl alcohol (Ph–CH₂–OH) from bromobenzene (Ph–Br)

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

c.

How could the following compounds be prepared, using cyclohexene as a starting material?

a.

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

b.

Which of the reactions cannot be used for the synthesis of isobutyl alcohol?

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

(c)

What reagents should be used to carry out the following syntheses?

What reagents should be used to carry out the following syntheses?

Starting with cyclohexene, how can the following compounds be prepared?

a. methoxycyclohexane

Using 1,2-dimethylcyclohexene 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.) If a chiral product is shown, assume that it is part of a racemic mixture.

(f)