13. Alcohols and Carbonyl Compounds

In a Grignard reaction, which key feature is formed as a result of the reaction between a Grignard reagent and a carbonyl compound?

Based on the stereochemical result alone, how can you tell that this reaction does not proceed by an Sₙ2 mechanism?

Starting with cyclohexane, how could the following compounds be prepared?

e.

Fill in the boxes:

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.

c. 1-ethylcyclopentanol

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

(c)

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)

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

Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.

b. 1-phenylpropene

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

(b)

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

(c) trans-oct-3-ene

Predict the product of the following reactions.

(a)

The Grignard reaction is based on the chemistry of what type of species?

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