How would you prepare 2-methyl-2-propanol via a grignard with dimethyl carbonate as your carbonyl source? show all reagents?

The Grignard reagent serves as a very important tool in the synthesis of many other compounds.

The Grignard reagent serves as a very important tool in the synthesis of many other compounds. Grignard reagent are used in the synthesis of alcohols, ethers etc.

All the reagents and compounds required for the synthesis of 2-methyl-2-propanol via a Grignard reagent  with dimethyl carbonate  are shown in the image attached to this answer.

Learn more about Grignard reagent: link

React it with CH₃MgBr and work up the product with saturated ammonium chloride solution

Explanation:

Grignard reagents convert esters into tertiary alcohols.

The general equation is

The Grignard reagent in this synthesis is methylmagnesium bromide. You prepare it by reacting a solution methyl bromide in anhydrous ether with magnesium and a few crystals of iodine.

The reaction consumes 3 mol of CH₃MgBr per mole of dimethyl carbonate, and everything happens in the same pot.

Acid workup of the product usually involves the addition of a saturated aqueous solution of ammonium chloride and extraction with a low-boiling organic solvent.

The mechanism involves:

Step 1. Nucleophilic attack and loss of leaving group

(a) The Grignard reagent attacks the carbonyl of dimethyl carbonate, followed by (b) the loss of a methoxide leaving group.

Step 2. Nucleophilic attack and loss of leaving group

(a) A second mole of the Grignard reagent attacks the carbonyl of methyl acetate, followed by (b) the loss of a methoxide leaving group.

Step 3. Nucleophilic attack and protonation of the adduct.  

(a) A third mole of the Grignard reagent attacks the carbonyl of acetone, followed by (b) protonation of the alkoxide to form 2-methylpropan-2-ol.

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