04.03A · Chapitres 5-7 — cours

Chapters 5-7 — course

Core lectures · 61 pages

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Chapter 5 Review

1Imine Formation from Carbonyls 2Imine Reduction to Amines 3Transamination & Pyridoxal Phosphate

Nucleophilic Substitution & Leaving Groups

4Tetrahedral Intermediate & Selectivity 5Leaving Group Ranking by pKa

6Acid-Base Summary 7Chapter 5 Summary 8Cumulative Reaction Summary

Chapter 6: Acids, Esters, Amides & Proteins

9Course Table of Contents

Carboxylic Acid Derivatives Overview

10Carbonyl Routes to Esters & Amides

Carboxylic Acids

11Resonance, Electrophilicity & Acidity 12H-Bonds, Dimers & Carboxylate Salts 13Acid-Base pKa Summary 14Resonance Stabilization of Carboxylate

Protein Synthesis

15Amide Bond Formation Challenge 16Carbonyl Routes: Ester & Amide Pathways

Fischer Esterification

17Acid-Catalyzed Mechanism 18Why Base Catalysis Fails

Ester Hydrolysis

19Saponification Mechanism

Biological Esters & Lipids

20Amphiphiles, Micelles & Biomembranes 21Reagent Selectivity Exercise

Thioester & Lactone Chemistry

22HMG-CoA Thioester Reduction to Mevalonate 23Acid-Base pKa Summary 24Lactone Hydrolysis & Lovastatin

Protein Synthesis (Continued)

25Carbonyl Derivative Interconversion Map 26Activated Ester & Peptide Bond Formation 27mRNA Codons & Translation 28Carbonyl Derivative Summary Map

Amide Hydrolysis

29Chemical & Enzymatic (Protease) Hydrolysis 30Paxlovid & Protease Inhibition

31Drug Applications Overview 32Cumulative Reaction Summary

Enolate & Carbon-Carbon Bond Chemistry

33Keto-Enol Tautomerism & Enolate Ion 34Glossary: Tautomers vs Resonance 35Aldol Addition Mechanism 36Aldol Dehydration to Conjugated Enone 37Claisen Condensation — Biological Context 38Claisen Condensation Mechanism 39β-Ketoester Decarboxylation to Ketone

40Chapter 6 Summary 41Cumulative Reaction Summary (Updated)

Chapter 7: Nucleic Acids & Amines

42Course Table of Contents

sp³ Nitrogen & Alkylamines

43Pyramidal Geometry & N-H Hydrogen Bonds 44Alkylamine as Base (pKa ~10)45Acid-Base pKa Summary

46Amide & Arylamine — Weak Bases 47DNA Base Pairing (G-C, A-T)

4820 Amino Acids as Zwitterions

Amine Nucleophilic Reactions

49MeNH₂ Addition-Elimination at sp² C

SN2 Nucleophilic Substitution

50Polycyclic Aromatic Hydrocarbon & DNA Alkylation 51Transition State & Inversion of Configuration 52Leaving Group & Steric Effects 53Biological SN2: Norepinephrine → Adrenaline

Aromatic Heterocycles & Nucleic Acids

54Deoxyribonucleotide Structures (A, G, C, T)55Aromaticity Definition (4n+2 Rule)56Pyridine & Pyrimidine (6π Electrons)57Pyrrole, Imidazole, Indole & Purine

Amino Acids & Genetic Code Recap

58All 20 Amino Acids (Named)59Base Pairing & Double Helix 60Molnupiravir & Base-Pairing Mimicry

61Chapter 7 Summary

04.03APage 1Chapter 5 ReviewIminesImine Formation from Carbonyls

Chapitres 5-7 — cours page 1

04.03APage 2Chapter 5 ReviewIminesImine Reduction to Amines

Chapitres 5-7 — cours page 2

04.03APage 3Chapter 5 ReviewIminesTransamination & Pyridoxal Phosphate

Chapitres 5-7 — cours page 3

04.03APage 4Chapter 5 ReviewNucleophilic Substitution & Leaving GroupsTetrahedral Intermediate & Selectivity

Chapitres 5-7 — cours page 4

04.03APage 5Chapter 5 ReviewNucleophilic Substitution & Leaving GroupsLeaving Group Ranking by pKa

Chapitres 5-7 — cours page 5

04.03APage 6Chapter 5 ReviewAcid-Base Summary

Chapitres 5-7 — cours page 6

04.03APage 7Chapter 5 ReviewChapter 5 Summary

Chapitres 5-7 — cours page 7

04.03APage 8Chapter 5 ReviewCumulative Reaction Summary

Chapitres 5-7 — cours page 8

04.03APage 9Chapter 6: Acids, Esters, Amides & ProteinsCourse Table of Contents

Chapitres 5-7 — cours page 9

04.03APage 10Chapter 6: Acids, Esters, Amides & ProteinsCarboxylic Acid Derivatives OverviewCarbonyl Routes to Esters & Amides

Chapitres 5-7 — cours page 10

04.03APage 11Chapter 6: Acids, Esters, Amides & ProteinsCarboxylic AcidsResonance, Electrophilicity & Acidity

Chapitres 5-7 — cours page 11

04.03APage 12Chapter 6: Acids, Esters, Amides & ProteinsCarboxylic AcidsH-Bonds, Dimers & Carboxylate Salts

Chapitres 5-7 — cours page 12

04.03APage 13Chapter 6: Acids, Esters, Amides & ProteinsCarboxylic AcidsAcid-Base pKa Summary

Chapitres 5-7 — cours page 13

04.03APage 14Chapter 6: Acids, Esters, Amides & ProteinsCarboxylic AcidsResonance Stabilization of Carboxylate

Chapitres 5-7 — cours page 14

04.03APage 15Chapter 6: Acids, Esters, Amides & ProteinsProtein SynthesisAmide Bond Formation Challenge

Chapitres 5-7 — cours page 15

04.03APage 16Chapter 6: Acids, Esters, Amides & ProteinsProtein SynthesisCarbonyl Routes: Ester & Amide Pathways

Chapitres 5-7 — cours page 16

04.03APage 17Chapter 6: Acids, Esters, Amides & ProteinsFischer EsterificationAcid-Catalyzed Mechanism

Chapitres 5-7 — cours page 17

04.03APage 18Chapter 6: Acids, Esters, Amides & ProteinsFischer EsterificationWhy Base Catalysis Fails

Chapitres 5-7 — cours page 18

04.03APage 19Chapter 6: Acids, Esters, Amides & ProteinsEster HydrolysisSaponification Mechanism

Chapitres 5-7 — cours page 19

04.03APage 20Chapter 6: Acids, Esters, Amides & ProteinsBiological Esters & LipidsAmphiphiles, Micelles & Biomembranes

Chapitres 5-7 — cours page 20

04.03APage 21Chapter 6: Acids, Esters, Amides & ProteinsBiological Esters & LipidsReagent Selectivity Exercise

Chapitres 5-7 — cours page 21

04.03APage 22Chapter 6: Acids, Esters, Amides & ProteinsThioester & Lactone ChemistryHMG-CoA Thioester Reduction to Mevalonate

Chapitres 5-7 — cours page 22

04.03APage 23Chapter 6: Acids, Esters, Amides & ProteinsThioester & Lactone ChemistryAcid-Base pKa Summary

Chapitres 5-7 — cours page 23

04.03APage 24Chapter 6: Acids, Esters, Amides & ProteinsThioester & Lactone ChemistryLactone Hydrolysis & Lovastatin

Chapitres 5-7 — cours page 24

04.03APage 25Chapter 6: Acids, Esters, Amides & ProteinsProtein Synthesis (Continued)Carbonyl Derivative Interconversion Map

Chapitres 5-7 — cours page 25

04.03APage 26Chapter 6: Acids, Esters, Amides & ProteinsProtein Synthesis (Continued)Activated Ester & Peptide Bond Formation

Chapitres 5-7 — cours page 26

04.03APage 27Chapter 6: Acids, Esters, Amides & ProteinsProtein Synthesis (Continued)mRNA Codons & Translation

Chapitres 5-7 — cours page 27

04.03APage 28Chapter 6: Acids, Esters, Amides & ProteinsProtein Synthesis (Continued)Carbonyl Derivative Summary Map

Chapitres 5-7 — cours page 28

04.03APage 29Chapter 6: Acids, Esters, Amides & ProteinsAmide HydrolysisChemical & Enzymatic (Protease) Hydrolysis

Chapitres 5-7 — cours page 29

04.03APage 30Chapter 6: Acids, Esters, Amides & ProteinsAmide HydrolysisPaxlovid & Protease Inhibition

Chapitres 5-7 — cours page 30

04.03APage 31Chapter 6: Acids, Esters, Amides & ProteinsDrug Applications Overview

Chapitres 5-7 — cours page 31

04.03APage 32Chapter 6: Acids, Esters, Amides & ProteinsCumulative Reaction Summary

Chapitres 5-7 — cours page 32

04.03APage 33Chapter 6: Acids, Esters, Amides & ProteinsEnolate & Carbon-Carbon Bond ChemistryKeto-Enol Tautomerism & Enolate Ion

Chapitres 5-7 — cours page 33

04.03APage 34Chapter 6: Acids, Esters, Amides & ProteinsEnolate & Carbon-Carbon Bond ChemistryGlossary: Tautomers vs Resonance

Chapitres 5-7 — cours page 34

04.03APage 35Chapter 6: Acids, Esters, Amides & ProteinsEnolate & Carbon-Carbon Bond ChemistryAldol Addition Mechanism

Chapitres 5-7 — cours page 35

04.03APage 36Chapter 6: Acids, Esters, Amides & ProteinsEnolate & Carbon-Carbon Bond ChemistryAldol Dehydration to Conjugated Enone

Chapitres 5-7 — cours page 36

04.03APage 37Chapter 6: Acids, Esters, Amides & ProteinsEnolate & Carbon-Carbon Bond ChemistryClaisen Condensation — Biological Context

Chapitres 5-7 — cours page 37

04.03APage 38Chapter 6: Acids, Esters, Amides & ProteinsEnolate & Carbon-Carbon Bond ChemistryClaisen Condensation Mechanism

Chapitres 5-7 — cours page 38

04.03APage 39Chapter 6: Acids, Esters, Amides & ProteinsEnolate & Carbon-Carbon Bond Chemistryβ-Ketoester Decarboxylation to Ketone

Chapitres 5-7 — cours page 39

04.03APage 40Chapter 6: Acids, Esters, Amides & ProteinsChapter 6 Summary

Chapitres 5-7 — cours page 40

04.03APage 41Chapter 6: Acids, Esters, Amides & ProteinsCumulative Reaction Summary (Updated)

Chapitres 5-7 — cours page 41

04.03APage 42Chapter 7: Nucleic Acids & AminesCourse Table of Contents

Chapitres 5-7 — cours page 42

04.03APage 43Chapter 7: Nucleic Acids & Aminessp³ Nitrogen & AlkylaminesPyramidal Geometry & N-H Hydrogen Bonds

Chapitres 5-7 — cours page 43

04.03APage 44Chapter 7: Nucleic Acids & Aminessp³ Nitrogen & AlkylaminesAlkylamine as Base (pKa ~10)

Chapitres 5-7 — cours page 44

04.03APage 45Chapter 7: Nucleic Acids & Aminessp³ Nitrogen & AlkylaminesAcid-Base pKa Summary

Chapitres 5-7 — cours page 45

04.03APage 46Chapter 7: Nucleic Acids & Aminessp² NitrogenAmide & Arylamine — Weak Bases

Chapitres 5-7 — cours page 46

04.03APage 47Chapter 7: Nucleic Acids & Aminessp² NitrogenDNA Base Pairing (G-C, A-T)

Chapitres 5-7 — cours page 47

04.03APage 48Chapter 7: Nucleic Acids & AminesAmino Acids20 Amino Acids as Zwitterions

Chapitres 5-7 — cours page 48

04.03APage 49Chapter 7: Nucleic Acids & AminesAmine Nucleophilic ReactionsMeNH₂ Addition-Elimination at sp² C

Chapitres 5-7 — cours page 49

04.03APage 50Chapter 7: Nucleic Acids & AminesSN2 Nucleophilic SubstitutionPolycyclic Aromatic Hydrocarbon & DNA Alkylation

Chapitres 5-7 — cours page 50

04.03APage 51Chapter 7: Nucleic Acids & AminesSN2 Nucleophilic SubstitutionTransition State & Inversion of Configuration

Chapitres 5-7 — cours page 51

04.03APage 52Chapter 7: Nucleic Acids & AminesSN2 Nucleophilic SubstitutionLeaving Group & Steric Effects

Chapitres 5-7 — cours page 52

04.03APage 53Chapter 7: Nucleic Acids & AminesSN2 Nucleophilic SubstitutionBiological SN2: Norepinephrine → Adrenaline

Chapitres 5-7 — cours page 53

04.03APage 54Chapter 7: Nucleic Acids & AminesAromatic Heterocycles & Nucleic AcidsDeoxyribonucleotide Structures (A, G, C, T)

Chapitres 5-7 — cours page 54

04.03APage 55Chapter 7: Nucleic Acids & AminesAromatic Heterocycles & Nucleic AcidsAromaticity Definition (4n+2 Rule)

Chapitres 5-7 — cours page 55

04.03APage 56Chapter 7: Nucleic Acids & AminesAromatic Heterocycles & Nucleic AcidsPyridine & Pyrimidine (6π Electrons)

Chapitres 5-7 — cours page 56

04.03APage 57Chapter 7: Nucleic Acids & AminesAromatic Heterocycles & Nucleic AcidsPyrrole, Imidazole, Indole & Purine

Chapitres 5-7 — cours page 57

04.03APage 58Chapter 7: Nucleic Acids & AminesAmino Acids & Genetic Code RecapAll 20 Amino Acids (Named)

Chapitres 5-7 — cours page 58

04.03APage 59Chapter 7: Nucleic Acids & AminesAmino Acids & Genetic Code RecapBase Pairing & Double Helix

Chapitres 5-7 — cours page 59

04.03APage 60Chapter 7: Nucleic Acids & AminesAmino Acids & Genetic Code RecapMolnupiravir & Base-Pairing Mimicry

Chapitres 5-7 — cours page 60

04.03APage 61Chapter 7: Nucleic Acids & AminesChapter 7 Summary

Chapitres 5-7 — cours page 61