13. Alcohols and Carbonyl Compounds

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.

a. CH₃CH(OD)CD₃

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(f)

(g)

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

(a)

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

c. dicyclohexylphenylmethanol

In Chapters 8 and 17 we learn two reactions for the synthesis of the alcohol shown. (a) Show a mechanism for each of the reactions. (b) If you were designing a synthetic route, which would be considered more sustainable? Consider all factors. [Assume the starting organic molecules are equally green.]

Predict the product of the following epoxide opening reactions.

(b)

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 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)

Predict the products formed when cyclohexanone reacts with the following reagents.

(f) PhMgBr and then mild H₃O⁺

Propose a mechanism for the reaction of acetyl chloride with phenylmagnesium bromide to give 1,1-diphenylethanol.

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.

d. Ph(CD₃)₂COD

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

d. 2-cyclopentylpentan-2-ol

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.

b. CH₃C(OH)(CD₃)₂

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

(a)

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

(e) an alkene

(f) ethylene oxide