13. Alcohols and Carbonyl Compounds

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

b.

Using bromocyclohexane as a starting material, how could you synthesize the following compounds?

d.

How can the following compounds be prepared from the given starting materials?

c.

Show how each of the following compounds can be prepared, using the given starting material:

e.

Identify A through O:

a. Show the reagents required to form the primary alcohol in each of the following reactions.

a. Show the reagents required to form the primary alcohol in each of the following reactions.

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(c)

Predict the major products of the following reactions.

(d)

Two of the methods for converting alkyl halides to carboxylic acids are covered in Sections 20-8B and 20-8C. One is formation of a Grignard reagent followed by addition of carbon dioxide and then dilute acid. The other is substitution by cyanide ion, followed by hydrolysis of the resulting nitrile. For each of the following conversions, decide whether either or both of these methods would work, and explain why. Show the reactions you would use.

(a)

(b)

Predict the products of the following reactions.

(a) sec-butylmagnesium iodide + D₂O

(b) n-butyllithium + CH₃CH₂OH

(c) isobutylmagnesium bromide + but-1-yne

Point out the flaws in the following incorrect Grignard syntheses.

(a)

Show how you would accomplish the following synthetic conversions.

(c)

Show how you would accomplish the following synthetic conversions.

(d)

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.