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Generally 20 mg levitra super active, negatively charged species are better nucleophiles than analogous neutral species buy levitra super active 40mg low price. Basicity and nucleophilicity Basicity is deﬁned by the equilibrium constant for abstracting a proton levitra super active 40mg with visa. On the other hand generic 40mg levitra super active mastercard, a nucleophile forms a new bond with an atom other than a proton. Species with a negative charge are stronger nucleophiles than analogous species without a negative charge. The more electronegative elements hold on more tightly to their nonbonding electrons. Fluoride is a nucleophile having hard or low polarizability, with its electrons held close to the nucleus, and it must approach the carbon nucleus closely before orbital overlap can occur. The outer shell of the soft iodide has loosely held electrons, and these can easily shift and overlap with the carbon atom at a relatively long distance. Solvent effects Different solvents have different effects on the nucleophi- licity of a species. Solvents with acidic protons are called protic solvents, usually OÀÀHorNÀÀH groups. F , can be solvated so well in polar protic solvents that their nucleophilicity is reduced by the solvation. Steric effects Base strength is relatively unaffected by steric effect, because a base removes a relatively unhindered proton. Thus, the strength of a base depends only on how well the base shares its electrons with a proton. A 3 bulky nucleophile has difﬁculty in getting near the backside of the sp carbon. Steric effects of the substrate Large groups on the electrophile hinder the approach of the nucleophile. Generally, one alkyl group slows the reaction, two alkyl groups make it difﬁcult and three alkyl groups make it close to impossible. The reaction is stereospeciﬁc since a certain stereoisomer reacts to give one speciﬁc stereoisomer as product. Conversion of alkyl halides Williamson ether synthesis: preparation of ether The sodium or potas- À sium alkoxides are strong bases and nucleophiles. Alkyl azides are easily prepared from sodium or potassium azides and alkyl halides. The reaction mechanism for the 2 N formation of 1 amine is similar to the formation of nitrile. The formation of ester follows 2 N a similar mechanism to the formation of alkyne. Preparation of alkanes The coupling reaction is a good synthetic way to join two alkyl groups 0 together. The reaction is limited to primary alkyl halide, but the alkyl groups in the Gilman reagents may be 1 ,2 or 3. The nucleophilic substitution reaction of alcohols only occurs in the presence of an acid. Protonation to convert the leaving group to H2O has limited utility, as not all substrates or nucleophiles can be utilized under acidic conditions without unwanted side reactions. An alternative is to convert the alcohol into alkyl halide or alkyl tosylate (see below), which has a much 5. Acid-catalysed condensation of alcohols: preparation of ethers Bimolecular dehydration is generally used for the synthesis of symmetrical ethers from unhindered 1 alcohols. In this reaction, ethanol 2 4 is protonated in the presence of an acid, which is then attacked by another molecule of ethanol to give diethyl ether. Without the use of ZnCl , the S 2 reaction is 2 N slow, because chloride is a weaker nucleophile than bromide. The ZnCl2 coordinates to the hydroxyl oxygen, and generates a better leaving group. Thionyl chloride converts the hydroxyl group in an alcohol to a chlorosulphite leaving group that can be displaced by the chloride.
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