13. Alcohols and Carbonyl Compounds

Show two ways you could synthesize each of the following secondary alcohol by adding an appropriate Grignard reagent to an aldehyde.

(c)

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

c. 1-ethylcyclopentanol

Show how you would add Grignard reagent to acid chloride or ester to synthesize the following alcohols.

c. dicyclohexylphenylmethanol

Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide.

(c)

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

(d) 2-cyclohexylethanol from bromocyclohexane

Show how this 1° alcohol can be made from the following:

(e) an alkene

(f) ethylene oxide

Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.

(b)

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

d. 2-cyclopentylpentan-2-ol

Point out the flaws in the following incorrect Grignard syntheses.

(c)

(d)

A variety of organometallics, which as strong nucleophiles can react with epoxides, are introduced in Chapter 16. Predict the product of these reactions. [Hint: Assume the carbon–metal bond in each is ionic, with the carbon possessing the negative charge.]

(b)

Predict the product of the following epoxide addition reactions.

(b)

Addition to an epoxide occurs via an S_N2 reaction, but the stereochemistry of the epoxide is retained in the following reaction. Why?

Show how you would synthesize the following:

f. 2,5-dimethylhexane from a four-carbon alkyl halide

Predict the products of the following reactions.

(a) allyl bromide + cyclohexyl magnesium bromide

Show how the reaction of an allylic halide with a Grignard reagent might be used to synthesize the following hydrocarbons.

c. 1-cyclopentylpent-2-ene