Advanced Organic Chemistry. Reactions and Synthesis by Carey F., Sundberg R.

By Carey F., Sundberg R.

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HA]). Similar definitions apply to general base and specific base catalysis involving base and hydroxide ion respectively. The Equations 31 donating an electron pair to carbon or other electrophilic centres. 22This relationship is called an extended Brmsted equation; it often breaks down when the gross structure of the nucleophile is changed, such as from carboxylate ions to amines, azide ion or halide ions. The reverse process, the expulsion of a leaving group from a carbon or other centre, generates a base.

The Brmsted Equation is preferred and in all the arguments in this chapter we shall use p terminology. ) are perfectly valid vehicles for determining effective charge. ' This expression also means that when the equilibrium is favourable to products the overall rate constant kob,= k , and when the equilibrium is unfavourable kobs= k,. These pitfalls only trap the unwary if kobsis measured as the rate constant for approuch to equilihriurn of the system. 60 Chapter 3 of the substituted phenol are required to compute k-, from the return rate of the neutral AcIm to phenyl acetate (Equation 12).

00163 3 Using the tables in Appendix 3 indicate the relative inductive electron withdrawing power of 0,N-, C1-, NC-, MeOCO-, MeCO-, MeO-, and Me- compared to H in solution reactions. 50Graph the Hammett relationships and comment on the relative values of the Hammett slopes. 02Co. The Hammett p parameter is close to that for benzoic acids. What can you deduce from this about which hydrogen is ionising? 6 Explain why the substituent effect in the dissociation of substituted 2-arylpropionic acids is less than that for the dissociation of substituted benzoic acids.

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