13. Alcohols and Carbonyl Compounds

Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

(b)

What is the product of each of the following reactions?

b.

Predict the product of the reaction

Show how you would add a Grignard reagent to an ester or a nitrile to synthesize

(a) 4-phenylheptan-4-ol.

Give the structures of intermediates A through H in the following synthesis of trans-1-cyclohexyl-2-methoxycyclohexane.

What alkyl halide reacts with lithium divinylcuprate [(CH₂=CH)₂CuLi] for the synthesis of each of the following compounds?

c.

d.

Phenol oxidation can be coupled with other reactions to form new C―C bonds using reactions studied previously. Predict the product of the following series of reactions.

(b)

Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr₃, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4-dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.

Predict the product of the reaction

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.

(c)

What starting material is required in order to synthesize each of the following compounds by ring-closing metathesis?

a.

What products are obtained from metathesis of each of the following alkenes?

a. CH₃CH₂CH=CH₂

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

(b)

Predict the product of the diorganocuprate cross-coupling reactions shown.

(c)

What is the major product of each of the following reactions?

c.

d.