13. Alcohols and Carbonyl Compounds

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

(g) cyclopentylphenylmethanol from benzaldehyde (Ph–CHO)

Show how to make these deuterium-labeled compounds, using CD₃MgBr and D₂O as your sources of deuterium, and any non-deuterated starting materials you wish.

c. CD₃CH₂CH₂OH

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

(c) an ester

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

(c)

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)