2444-112811 - Chapter 22 Enolate Anions Acyl Addition and...

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Chapter 22: Enolate Anions: Acyl Addition and Acyl Substitution 1 • There are other carbon acids, specifically involving the proton on an ! -carbon in aldehydes, ketones or esters. • With a suitable base, these carbonyl compounds generate a new type of carbon nucleophile called an enolate anion.
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To begin, you should know: 2 • Nomenclature for aldehydes, ketones and acid derivatives. (chapter 5, section 5.9 and chapter 16, sections 16.2, 16.4) • The acid-base reaction, and factors that contribute to the position of the acid-base equilibrium. (chapter 6, sections 6.1, 6.3) • What contributes to acid strength. (chapter 6, section 6.3) • What contributes to base strength. (chapter 6, section 6.4) • The fundamentals of kinetic and thermodynamic controlled reactions. (chapter 7, sections 7.6, 7.7, 7.10) • The fundamentals of equilibrium reactions and factors that influence the position of the equilibrium. chapter 7, section 7.10 • The concept of resonance and resonance stability. (chapter 5, section 5.9.C) • Be able to draw resonance contributors and understand their significance. (chapter 5, section 5.9.C and chapter 21, section 21.3) • Rate of reaction. (chapter 7, section 7.11) • Rotamers and conformations. (chapter 8, sections 8.1, 8.4) • Know the reactions that generate ketones and aldehydes. (chapter 17, section 17.2 and chapter 21, section 21.3.C) • Keto-enol tautomerism. (chapter 10, sections 10.6.C, 10.6.D and chapter 18, section 18.5) • The E2 reaction. (chapter 12, sections 12.1, 12.2) • The SN2 reaction with alkyl halides. (chapter 11, sections 11.1, 11.2, 11.3) • Understand differences in nucleophilic strength. (chapter 11, section 11.3) Formation of Grignard reagents and organolithium reagents. (chapter 15, section 15.1, 15.5) • Grignard reagents and organolithium reagents are strong bases. (chapter 15, sections 15.3, 15.5.B)
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To begin, you should know: 3 • Amines react as acids in the presence of a strong base. (chapter 15, section 15.5.B and chapter 6, section 6.4.A) • Acyl addition reactions of nucleophiles. (chapter 16, section 16.3 and chapter 18, section 18.1) • Acyl addition of organometallic reagents to aldehydes and ketones. (chapter 18, section 18.4) • The reaction of alcohols and amines with aldehydes and ketones. (chapter 18, sections 18.6, 18.7) • Know the reactions that generate carboxylic acids. (chapter 17, section 17.4 and chapter 20, section 20.2) • Know the reactions that generate acid derivatives. (chapter 20, sections 20.3-20.6) • Acyl substitution reactions. (chapter 16, section 16.8 and chapter 20, section 20.1) • Recognize electron releasing and withdrawing substituents. (chapter 3, section 3.7 and chapter 21, section 21.3) • How to identify a good leaving group. (chapter 11, section 11.2) • Know how to convert alkoxide anions to the corresponding alcohol via an acid-base workup. (chapter 5, section 5.7 and chapter 6, section 6.2 and chapter 18, section 18.1) • E- and Z nomenclature. (chapter 9, section 9.4) • Absolute configuration and stereogenic centers. (chapter 9, sections 9.1, 9.3) • Diastereomers. (chapter 9, section 9.5) • Decarboxylation. (chapter 12, section 12.6)
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When completed, you should know: 4 • The !
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