Uses of grignard reagent

The Grignard Reaction is the addition of an organomagnesium halide (Grignard reagent) to a ketone(H20) or aldehyde, to form a tertiary or secondary alcohol, respectively. The reaction ith formaldehyde leads to a primary alcohol. Grignard Reagents are also used in the follo ing important reactions! The addition of an e"cess of a Grignard reagent to an ester or lactone gives a tertiary alcohol in hich t o alkyl groups are the same, and the addition of a Grignard reagent to a nitrile produces an unsymmetrical ketone via a metalloimine intermediate are formed #y the reaction of magnesium metal ith alkyl or alkenyl halides. They$re e"tremely good nucleophiles, reacting ith electrophiles such as car#onyl compounds (aldehydes, ketones, esters, car#on dio"ide, etc) and epo"ides. They$re also very strong #ases and ill react ith acidic hydrogens (such as alcohols, ater, and car#o"ylic acids). Grignard reagents are made through the addition of magnesium metal to alkyl or alkenyl halides. The halide can #e %l, &r, or ' (not (). 't$s slightly easier to make Grignards from the iodides and #romides, ho ever. )ote hat$s happening here * the magnesium is +inserting, itself #et een the car#on and the halide. This halide the +-, referred to hen e refer to Grignard reagents as +Rmg-,.

.ne of the most common uses of Grignard reagents is in their reaction ith aldehydes and ketones to form alcohols. 'n the first step, the Grignard forms the car#on/car#on #ond. This results in an alko"ide (the con0ugate #ase of an alcohol). To form the alcohol, it$s necessary to add acid at the end of the reaction (in hat$s called the + orkup, step). This is sho n here as +H1.2, (the +-, is 0ust the counter/ion, a spectator here)

The reaction #ehaves similarly ith ketones. 3gain, there$s nothing special a#out the %l here * it all depends on ho you made the Grignard in the first place.

Grignard reagents ill also add to esters. 4hat makes these reactions a little more complicated is that they add t ice. The net result (after addition of acid) is a tertiary alcohol. This is also the case for acid halides (acyl halides) and anhydrides. .ne nota#le e"ception is car#o"ylic acids.

3nother important reaction of Grignard reagents is that they ill add to epo"ides to form car#on/car#on #onds. .ne thing to keep in mind here is that the tendency is for them to add to the less su#stituted end of the epo"ide * that is, the less sterically hindered end. 5ou can think of this reaction as #eing essentially similar to an 6)2 reaction. 3fter addition of acid, an alcohol is o#tained.

Grignard reagents also add to car#on dio"ide (%.2) to form car#o"ylates, in a reaction similar to their reactions ith ketones and aldehydes. The car#o"ylates are converted to car#o"ylic acids after addition of acid (such as our trusty H1.(2) ).

(inally, since Grignard reagents are essentially the con0ugate #ases of alkanes, they$re also e"tremely strong #ases. This means that sometimes acid/#ase reactions can compete ith their nucleophilic addition reactions. .ne common situation here this crops up is hen Grignard reagents are added to car#o"ylic acids. 'nstead of adding to the car#onyl, they react ith the proton instead and form the car#o"ylate salt.

This can also #e used to convert alkyl halides to alkanes. (irst you treat it ith magnesium, and then you treat the Grignard ith a strong acid. This gives you the alkane. 5ou can also use this to introduce deuterium (7) into molecules8 The first step is to make the Grignard reagent. The second is to treat that Grignard ith a deuterated acid such as 72.. This gives you the deuterated alkane.

'n the reaction of Grignards ith aldehydes, the car#on attacks the car#onyl car#on and performs a 9,2/addition to give an alko"ide. 'n the second step, acid is added to give you the alcohol. 7egradation of Grignard reagents and other uses! 3t one time, the formation and hydrolysis of Grignard reagents as used in the determination of the num#er of halogen atoms in an organic compound. 'n modern usage, Grignard degradation is used in the chemical analysis of certain triacylglycerols. 3lso, an e"ample of the Grignard reaction is a key step in the industrial production of Tamo"ifen (currently used for the treatment of osteopororsis and estrogen receptor positive #reast cancer in omen.)