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acetylenic protons have acidities on the same order of magnitude as those associated with
esters and amines.
2.8 SUMMARY
This chapter focused on the definition of acids as applied to organic molecules.
Furthermore, the impacts of electronegativities and functional groups on the acidities of
various types of protons were rationalized in the context of inductive effects. As discussions
advance throughout this topic and through organic chemistry coursework, a clear under-
standing of the various pK a values associated with different environments and how
they relate to one another will be beneficial. Consequently, a complete familiarization of
the pK a values presented in this chapter is essential. For convenience, all the pK a values
discussed in this chapter are listed in Appendix 1, and their general magnitudes
with respect to one another should be committed to memory. This is the only
recommended memorization task associated with this treatment of arrow pushing and
will greatly facilitate the development of skills enabling the prediction of the mechanistic
progression of organic reactions.
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