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A hydroxide ion acting as a nucleophile in an S N 2 reaction, converting a haloalkane into an alcohol. In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they ...
In the case below, tosylate is the best leaving group when ethoxide is the nucleophile, but iodide and even bromide become better leaving groups in the case of the thiolate nucleophile. [ 7 ] Relative rates for leaving groups ( k X / k Br ) in each reaction
In the intermediate step, the nucleophile is 185 degrees from the leaving group and the stereochemistry is inverted as the nucleophile bonds to make the product. Also, because the intermediate is partially bonded to the nucleophile and leaving group, there is no time for the substrate to rearrange itself: the nucleophile will bond to the same ...
Nucleophile strength is also affected by charge and electronegativity: nucleophilicity increases with increasing negative charge and decreasing electronegativity. For example, OH − is a better nucleophile than water, and I − is a better nucleophile than Br − (in polar protic solvents). In a polar aprotic solvent, nucleophilicity increases ...
If the nucleophile is a neutral molecule (i.e. a solvent) a third step is required to complete the reaction. When the solvent is water, the intermediate is an oxonium ion. This reaction step is fast. Deprotonation: Removal of a proton on the protonated nucleophile by water acting as a base forming the alcohol and a hydronium ion. This reaction ...
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The nucleophile is polarised and oriented by the base, which is itself bound and stabilised by the acid. [24] Catalysis is performed in two stages. First, the activated nucleophile attacks the carbonyl carbon and forces the carbonyl oxygen to accept an electron pair, leading to a tetrahedral intermediate. The resulting build-up of negative ...
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