Summary of Enolate Chemistry

Show how you could employ enamines in syntheses of the following compounds  

Halogenation of Aldehydes and Ketones (Sections 18.3B and 18.3C) General Reaction 

Direct Alkylation via Lithium Enolates (Section 18.4) General Reaction 

The key terms and concepts that are highlighted in bold, blue text within the chapter are defined in the glossary (at the back of the book) and have hyperlinked definitions in the PLUS accompanying WileyPLUS course (www.wileyplus.com) 

15 Rank the following in order of increasing acidity for the indicated hydrogen atoms (bold) (1 = least acidic 4 = most acidic). 

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Summary of Enolate Chemistry 847 [ WHY DO THESE TOPICS MATTER ] 849... 

For several tautomeric systems ketones/enols, imines/enamin and others) a distinct reversal of the stability order is observed when going from the neutral compounds to the radical cations, the first use of which in a new preparative a-Umpolung reaction has been documented for keto/enol systems. The present review provides a critical evaluation of the chemistry of enol radical cations in solution with a special emphasis on the Umpolung reaction and the intermediates thereof. Other enol type of radical cations are discussed with respect to their potential to provide a-carbonyl radical and a-carbonyl cation intermediates. Hence, this article does not constitute a comprehensive summary on all enol type of radical cation reactions. All potentials in this review are referenced versus SCE, unless noted otherwise. Potentials measured against the ferrocene/ferrocenium couple were converted to SCE by adding 0.334 V. 

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