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The olefins contained an EWG nitrile group and varying EDGs and the effect of varying EDGs on the rate of the addition reactions was observed. The process studied was: The process studied was: The rate of the addition reaction was accelerated by the following EDGs in increasing order: H < CH 3 < OCH 2 CH 3 .
The methyl group in toluene is small and will lead the ortho product being the major product. On the other hand, the t-butyl group is very bulky (there are 3 methyl groups attached to a single carbon) and will lead the para product as the major one. Even with toluene, the product is not 2:1 but having a slightly less ortho product.
An electron-withdrawing group (EWG) is a group or atom that has the ability to draw electron density toward itself and away from other adjacent atoms. [1] This electron density transfer is often achieved by resonance or inductive effects.
With nitrile electrophiles, nucleophilic addition take place by: [1] hydrolysis of a nitrile to form an amide or a carboxylic acid; organozinc nucleophiles in the Blaise reaction; alcohols in the Pinner reaction. the (same) nitrile α-carbon in the Thorpe reaction. The intramolecular version is called the Thorpe–Ziegler reaction.
The Blaise reaction is an organic reaction that forms a β-ketoester from the reaction of zinc metal with a α-bromoester and a nitrile. The reaction was first reported by Edmond Blaise (1872–1939) in 1901. The final intermediate is a metaloimine, which is then hydrolyzed to give the desired β-ketoester. The Blaise reaction
The cycle is completed by the reductive elimination of the nitrile. Lewis acids, such as triphenylboron (B(C 6 H 5) 3), induce reductive elimination of the nitrile product, increasing rates. [1] In the case of nickel-based systems, catalyst deactivation involves formation of dicyanonickel(II) species, which are unreactive toward alkenes.
The structure of a nitrile: the functional group is highlighted blue. In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group.The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH 3 CH 2 C≡N is called "propionitrile" (or propanenitrile). [1]
When the alkene carries a methylene group, elimination and addition can be concerted with transfer of an allyl proton to the carbonyl group which in effect is an ene reaction in scheme 6. Scheme 6. Carbonyl-ene reaction versus Prins reaction. in green: capture of the carbocation by additional carbonyl reactant.
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