Organic Chemisty II Past Lecture Slides
Lecture 1
Main topics include:
• Syllabus & i>clicker registration
• nomenclature and props of alcohols
• preparation/rxn of alcohols review
• synthetic strategies using above runs
• oxidation of alcohols (Swern, chromium reagents, HIO4)
• reduction of alcohols with hydride donors
• comparison to hydroboration
Main topics include:
• Syllabus & i>clicker registration
• nomenclature and props of alcohols
• preparation/rxn of alcohols review
• synthetic strategies using above runs
• oxidation of alcohols (Swern, chromium reagents, HIO4)
• reduction of alcohols with hydride donors
• comparison to hydroboration
The following lecture slides were presented during previous organic II courses. You may use these to study prior to lecture. Visit the Lecture Slides page to view the current semesters slides, which are always posted immediately after lecture. The current slides may contain significant differences in order and content. Always use the current slides to prepare for homework, quizzes and exams.
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Lecture 3
Main topics include:
• electrophilic aromatic subset. (review)
• O vs. C-acylation (synthesis of aspirin)
• O-alkylation of phenols
• ethers: naming and properties
• crown ethers and ethers as solvents
• conformational analysis of heterocycles
• prep. of ethers review
• epoxidation by peroxyacids
Main topics include:
• electrophilic aromatic subset. (review)
• O vs. C-acylation (synthesis of aspirin)
• O-alkylation of phenols
• ethers: naming and properties
• crown ethers and ethers as solvents
• conformational analysis of heterocycles
• prep. of ethers review
• epoxidation by peroxyacids
Lecture 4
Main topics include:
• acidic cleavage of ethers and phenols
• benzyl ethers as protecting groups
• ring opening of epoxides
• biological [O] of arenes and toxicity
• phenols by epoxide NIH shift
• Claisen rearrangement
• alkylation of thiols and sulfides
• biosynthetic methylation by SAM
Main topics include:
• acidic cleavage of ethers and phenols
• benzyl ethers as protecting groups
• ring opening of epoxides
• biological [O] of arenes and toxicity
• phenols by epoxide NIH shift
• Claisen rearrangement
• alkylation of thiols and sulfides
• biosynthetic methylation by SAM
Lecture 5
Main topics include:
• name of ketones and aldehydes
• carbonyl bond strength (σ vs. π)
• C=O polarity influence on bp and sol
• prep/rxns of aldehydes/ketones review
• hydration: Keq (steric vs. ground state)
• hyperconjugation and inductive effect on ground state (C=O) stability
• cyanohydrin formation; Keq
• benzoin condensation; umpolung
Main topics include:
• name of ketones and aldehydes
• carbonyl bond strength (σ vs. π)
• C=O polarity influence on bp and sol
• prep/rxns of aldehydes/ketones review
• hydration: Keq (steric vs. ground state)
• hyperconjugation and inductive effect on ground state (C=O) stability
• cyanohydrin formation; Keq
• benzoin condensation; umpolung
Lecture 6
Main topics include:
• types of carbonyl addition:
• formation of imines and enamines
• pH dependence on rate of formation
• Keq imine vs. enamine (BDE of C=N)
• stabilized imines
• semicarbazones from semicarbazide
• Schiff bases from pyridoxal phosphate
• reductive amination
• Wolf-Kishner reduction
Main topics include:
• types of carbonyl addition:
• formation of imines and enamines
• pH dependence on rate of formation
• Keq imine vs. enamine (BDE of C=N)
• stabilized imines
• semicarbazones from semicarbazide
• Schiff bases from pyridoxal phosphate
• reductive amination
• Wolf-Kishner reduction
Lecture 7
Main topics include:
• acetal formation; examples conditions
• mechanism; hemiacetal intermediate
• Dean-Stark trap with azeotropic diet.
• acetals protecting groups for carbonyl and diols
• stable hemiacetals; glucose mutarotation
• Wittig reaction; phosphorus ylides
• Wittig in synthesis
Main topics include:
• acetal formation; examples conditions
• mechanism; hemiacetal intermediate
• Dean-Stark trap with azeotropic diet.
• acetals protecting groups for carbonyl and diols
• stable hemiacetals; glucose mutarotation
• Wittig reaction; phosphorus ylides
• Wittig in synthesis
Lecture 8
Main topics include:
• carboxylic acids structure and naming
• boiling point and solubility
• acidity; substituent effect
• inferring nucleophilicity of benzene derivatives (rate of SE-Ar) from pKa
• percent ionization of acids
• salts of carboxylic acids
• micelles
Main topics include:
• carboxylic acids structure and naming
• boiling point and solubility
• acidity; substituent effect
• inferring nucleophilicity of benzene derivatives (rate of SE-Ar) from pKa
• percent ionization of acids
• salts of carboxylic acids
• micelles
Lecture 9
Main topics include:
• synthesis of carboxylic acids, review
• Grignard vs. nitrile synthesis of
• esterification through SN2
• Fisher esterification
• lactonization; macrolides
• mevalonolactone
• decarboxylation: diacids and b-ketoacids
• biological decarboxylations
Main topics include:
• synthesis of carboxylic acids, review
• Grignard vs. nitrile synthesis of
• esterification through SN2
• Fisher esterification
• lactonization; macrolides
• mevalonolactone
• decarboxylation: diacids and b-ketoacids
• biological decarboxylations
Lecture 10
Main topics include:
• carboxylic acid derivatives; naming
• addition/elimination mechanism
• reactivity of acid derivatives
• reactivity rationale; inductive/resonance
• conversion of acids to derivatives
• thionyl chloride in synthesis
• amides by DCC
• mixed anhydride method
Main topics include:
• carboxylic acid derivatives; naming
• addition/elimination mechanism
• reactivity of acid derivatives
• reactivity rationale; inductive/resonance
• conversion of acids to derivatives
• thionyl chloride in synthesis
• amides by DCC
• mixed anhydride method
Lecture 11
Main topics include:
• reactions of carboxylic acid derivatives
• alcohol amine chemoselectivity for acylation with acid chlorides and anhyd.
• saponification and transesterification
• making soap and bodiesel
• Grignard addition to esters and nitriles
• biological reactions of thioesters
• acetyl CoA in glucosamine synthesis
• synthesis of benzocaine
Main topics include:
• reactions of carboxylic acid derivatives
• alcohol amine chemoselectivity for acylation with acid chlorides and anhyd.
• saponification and transesterification
• making soap and bodiesel
• Grignard addition to esters and nitriles
• biological reactions of thioesters
• acetyl CoA in glucosamine synthesis
• synthesis of benzocaine
Lecture 12
Main topics include:
• enols and enolates
• pKas of carbonyl compounds
• kinetic vs thermodynamic enolates
• Aldol condensation; mixed; biological
• Claisen condensation
• cholesterol and fatty acid biosynthesis
• acylation of ketones
Main topics include:
• enols and enolates
• pKas of carbonyl compounds
• kinetic vs thermodynamic enolates
• Aldol condensation; mixed; biological
• Claisen condensation
• cholesterol and fatty acid biosynthesis
• acylation of ketones
Lecture 13
Main topics include:
• direct alkylation of enolate
• malonic acid synthesis
• decarboxylation mechanism
• acetoacetic ester synthesis
• 1,4- vs. 1,2-addition
• Gilman cuprate conjugate addition
• Michael addition
• Robinson annulation
• a-halogenation; Hell-Volhard-Zelinski
Main topics include:
• direct alkylation of enolate
• malonic acid synthesis
• decarboxylation mechanism
• acetoacetic ester synthesis
• 1,4- vs. 1,2-addition
• Gilman cuprate conjugate addition
• Michael addition
• Robinson annulation
• a-halogenation; Hell-Volhard-Zelinski
Lecture 14
Main topics include:
• classification; examples of alkaloids
• nomenclature
• basicity of alkyl and aryl amines
• substituting effects in aryl amines
• decreased basicity of aromatic amines
• amidine bases: imidazole and DBU
• amines at physiological pH
• amino acids; zwitterions at phys. pH
• solubility and extraction of amines
Main topics include:
• classification; examples of alkaloids
• nomenclature
• basicity of alkyl and aryl amines
• substituting effects in aryl amines
• decreased basicity of aromatic amines
• amidine bases: imidazole and DBU
• amines at physiological pH
• amino acids; zwitterions at phys. pH
• solubility and extraction of amines
Lecture 15
Main topics include:
• basicity of amines review
• basicity of histamine N-atoms
• development of cimetidine (Tagement)
• LAH reduction to amines
• amine alkylation; quaternary salts
• Gabriel amine synthesis
• Curtius rearrangement
• Hoffmann elimination/rule
• Hoffmann transition states
Main topics include:
• basicity of amines review
• basicity of histamine N-atoms
• development of cimetidine (Tagement)
• LAH reduction to amines
• amine alkylation; quaternary salts
• Gabriel amine synthesis
• Curtius rearrangement
• Hoffmann elimination/rule
• Hoffmann transition states
Lecture 16
Main topics include:
• SE-Ar with anilines; EDGs
• formation of diazonium ions
• substitution of diazonium ions (Sandmeyer reaction); in synthesis
• carbohydrate classification
• Fischer projections: review
• D and L aldohexoses
• anomers of pyranoses and furanoses
Main topics include:
• SE-Ar with anilines; EDGs
• formation of diazonium ions
• substitution of diazonium ions (Sandmeyer reaction); in synthesis
• carbohydrate classification
• Fischer projections: review
• D and L aldohexoses
• anomers of pyranoses and furanoses
Lecture 17
Main topics include:
• pyranose and furanose anomers
• mutarotation: calculation of ratio
• increased preference for alpha anomer: solvation and anomeric effects
• redox reactions of carbohydrates
• chain extension carbos: cyanohydrins
• chain shortening: Wohl degradation
• Koenigs-Knorr synthesis of glycoside
• osazone formation
Main topics include:
• pyranose and furanose anomers
• mutarotation: calculation of ratio
• increased preference for alpha anomer: solvation and anomeric effects
• redox reactions of carbohydrates
• chain extension carbos: cyanohydrins
• chain shortening: Wohl degradation
• Koenigs-Knorr synthesis of glycoside
• osazone formation
Lecture 18
Main topics include:
• disaccharides; 1,4 and 1,6 linages
• amino acids; structure
• using Henderson-Hasselbach to determine major form at specific pH
• classification of side-chains
• side chain Van der Waals interactions
• synthesis of amino acids: HVZ, reductive amination, Strecker, acetamidomalonate
Main topics include:
• disaccharides; 1,4 and 1,6 linages
• amino acids; structure
• using Henderson-Hasselbach to determine major form at specific pH
• classification of side-chains
• side chain Van der Waals interactions
• synthesis of amino acids: HVZ, reductive amination, Strecker, acetamidomalonate
Lecture 19
Main topics include:
• Arene oxidation; NIH shift
• Schiff bases of pyridoxal phosphate: decarboxylation, racemization, transamination
• peptides & amino acid analysis
• Sanger's reagent
• ninhydrin staining
• Edman degradation with PITC
• enzyme hydrolysis
Main topics include:
• Arene oxidation; NIH shift
• Schiff bases of pyridoxal phosphate: decarboxylation, racemization, transamination
• peptides & amino acid analysis
• Sanger's reagent
• ninhydrin staining
• Edman degradation with PITC
• enzyme hydrolysis
Lecture 20
Main topics include:
• amino acid protecting groups
• protein synthesis; Merrifield resin
• lipids: definition and types
• waxes, phospholipids, fats & oils,
• fatty acid biosynthesis
• soaps; saponification
• detergents
• biodiesel
Main topics include:
• amino acid protecting groups
• protein synthesis; Merrifield resin
• lipids: definition and types
• waxes, phospholipids, fats & oils,
• fatty acid biosynthesis
• soaps; saponification
• detergents
• biodiesel
Lecture 21
Main topics include:
•protaglandins and classification
• PGH2 biosynthesis
• cyclooxygenase inhibitors
• terpenes and terpenoids: classification
• mevalonate pathway; isopentenyl diphophate (IPP); limonene biosynth
• steroids; fused ring structure
• biosynthesis of lanosterol
Main topics include:
•protaglandins and classification
• PGH2 biosynthesis
• cyclooxygenase inhibitors
• terpenes and terpenoids: classification
• mevalonate pathway; isopentenyl diphophate (IPP); limonene biosynth
• steroids; fused ring structure
• biosynthesis of lanosterol
Lecture 22
Main topics include:
•ATP and phosphorylation
• structural basis for phosphorylation potential
• coupled reactions and Keq
• Glycolysis steps (aldolase and and dehydrogenase mechanisms)
• Link reaction: pyruvate to acetyl CoA
• thiamine pyrophosphate mechanism
• other fates of pyruvate
Main topics include:
•ATP and phosphorylation
• structural basis for phosphorylation potential
• coupled reactions and Keq
• Glycolysis steps (aldolase and and dehydrogenase mechanisms)
• Link reaction: pyruvate to acetyl CoA
• thiamine pyrophosphate mechanism
• other fates of pyruvate