Title: The Grignard Reaction

Objective: To prepare 2- Methyl-2-hexanol using Grignards reaction.

Materials required:

Clamps, graduated cylinder, thermometer, hotplate, magnetic stir bar, crystallizing dish with
sand, 25- mL round bottom flask, condenser, clips, iodine crystals, magnesium strips, ice water
bath, separatory funnel, boiling chip, erlenmeyer flasks, and beakers.

Chemicals required:
3 mL anhydrous diethyl ether, 1-bromobutane, acetone, 6 mL 3N hydrochloric acid, and
anyhydrous potassium carbonate.

Procedure:
1. To set up the apparatus for this experiment, get a hotplate and place a beaker with water on
top.
2. On a ring stand attach two clamps. Grab a condenser, round bottom flask and drying tube and
secure ends with clips, and attach to clamp. To the condenser attach a hose that connects to the
sink and attach a hose that leads from the condenser to the sink.
3. On the other clamp attach a thermometer, and place into beaker. Into the round bottom flask,
place a magnetic stirring bar and magnesium turnings.
4. Into the round bottom flask, pour 3 mL of anhydrous diethyl ether, and add 1.6 mL of
bromobutane to the diethyl ether, and attach reflux condenser promptly, and stir the solution, and
reaction should occur.
5. If solution does not boil, add a small crystal of iodine to clean the surface of the magnesium,
or it may be necessary to warm the solution. To do that, place a beaker with half full of warm tap
water on top of hotplate, and immerse the round bottom flask into the water, heat and continue to
stir. If solution is heated too much, in the beaker add cool tap water, and immerse the round
bottom flask into beaker. When exothermic reaction subsides, use beaker with warm tap water to
continue refluxing reaction mixture for fifteen minutes. When fifteen minutes are over, the
reaction mixture should be gray- black in color and should contain tiny particles from unreacted
magnesium.
6. You should have prepared n-butylmagnesium bromide, then remove the warm tap water from
beaker and add ice water instead. To the top of the reflux condenser, add approximately 3 mL of
acetone.
7. For isolation and purification of the product, To the n-butylmagnesium bromide solution
add 6 mL of 3 N hydrochloric acid in small portions over a ten minute period. With this addition,
continue to stir and cool reaction flask.
8. After the addition of hydrochloric acid, stop stirring mixture and transfer solution to separatory
funnel, two separate layers should be visible. Separate the organic layer from the aqueous layer.
9. Place the organic layer in a Erlenmeyer flask, and add several spatula tips of anhydrous
potassium carbonate, and swirl between the additions.
10. After the addition of anhydrous potassium carbonate, wait five minutes, then pour the dried
solution of the product into a clean 25 mL Erlenmeyer flask. Rinse the flask with 3 mL of diethyl
ether, and add rinse to the product.
11. To the flask add a boiling chip, and carefully heat in sand bath to remove bulk of diethyl ether
and unreacted acetone, continue heating until boiling ceases and only liquid product remains.
12. Transfer residual liquid to another Erlenmeyer flask and add magnetic spin bar.
13. To that solution add a few crystals of anhydrous potassium carbonate, and clamp Erlenmeyer
flask and place sand dish underneath. Into the flask attach a thermometer. Stir the liquid, and heat
to begin distillation. Collect the product of distillation at a lower literature boiling point; stop the
distillation before contents of vial boil to dryness. To test the purity of the solution, add a sodium
metal, a little fire should be seen.

Data and Results:

Compound Appearance
N- Butyl magnesium Grey color
bromide
Addition of acetone White precipitate formed
and anhydrous ether
Addition of HCl Layers formed: clear at top,
cloudy at bottom
2-methyl-2-hexanol Cloudy white precipitate,
with addition of Na little fire was seen after the
metal addition of sodium metal.

Discussion:

Grignard reagents are prepared by reaction of organo halides and magnesium metal. The reaction
takes place on the surface of the magnesium and involves single electron transfer, and the overall
result is an insertion of Mg into C-X bond. The magnesium is electron deficient, and electron
donating ethers is required to stabilize the reagents during reactions. The polar carbon metal
covalent bond causes grignards reagents to behave as carbanions, and are strong bases and
nucleophiles, therefore these compounds need to be handles well, and need to be prepared in
environments free of water and other protonated sources of chemicals. In this experiment, we
synthesized a tertiary alcohol from an alkyl halide and a ketone using a Grignard reaction.

Organic halides react with magnesium metal in diethyl ether to yield an organomagnesium
halide, and the carbon/magnesium bond is a highly polar covalent bond. The carbon atom is both
nucleophilic and basic, which makes it very reactive. The reaction mechanism of this reaction in
the first step includes the lewis acid magnesium ion forming an acid base complex with the basic
oxygen atom of the ketone, which makes the carbonyl group a better acceptor. The second step,
involves nucleophilic addition of butyl group to acetone, which produces a tetrahedral
intermediate. The third step of this reaction involves the tetrahedral intermediate reacting with
water when aqueous HCl is added, which undergoes hydrolysis to form the product alcohol.

When the Grignard reagent meets with water, the carbon atom is nucleophilic and basic, it reacts
with proton donors such as water to yield hydrocarbons.

Conclusion:
In conclusion our synthesis product of 2- methyl-2 hexanol was prepared by heating alkyl halide,
magnesium turnings, and ketone in diethyl ether under reflux to synthesize intermediate. The
intermediate was then hydrolyzed with HCl to produce a neutral product, and the product was
purified by extraction. The purity of the product was then determined with sodium metal. The
purity of our product was pure since it reacted with sodium metal, by producing a little fire.
Alcohols typically react with sodium metals to form salts and hydrogen.