[ 663ORCHOCHV18 ] VL Organic Chemistry 1 for Biological Chemistry

Workload Education level Study areas Responsible person Hours per week Coordinating university
4,5 ECTS B1 - Bachelor's programme 1. year Chemistry Wolfgang Schöfberger 3 hpw Johannes Kepler University Linz
Detailed information
Original study plan Bachelor's programme Biological Chemistry 2018W
Objectives Fundamentals of Organic Chemistry including spectroscopy
Subject Fundamentals of organic chemistry, functional groups, elementary reaction types, Basic spectroscopy (in particular NMR), nucleophilic aliphatic substitution reactions, reactions of carbonyl compounds; addition, elimination, reduction and oxidation reactions; reactions of aromatic compounds; rearrangement and pericyclic reactions; peptide chemistry

Chemistry of Alcohols, Glycols, Thiols, Ethers, Epoxides, and Sulfides

  • Oxidation and reduction
  • Oxidation to aldehydes, ketones, and carboxylic acids
  • Group equivalence
  • Thiol oxidation
  • Williamson synthesis
  • Ethers from alkene addition

Chemistry of Ethers, Epoxides, and Sulfides

  • Synthesis of epoxides
  • Cleavage of ethers
  • Nucleophilic substitution of epoxides
  • Glycol cleavage
  • Sulfonium salts
  • Neighbouring–group participation

Dienes, Allylic, and Benzylic Reactivity

  • Allenes (structure and stereochemistry)
  • Conjugated dienes (1,3-dienes)
  • Resonance & MO representation of conjugated π orbitals
  • Addition of hydrogen halides to conjugated dienes
  • Spectroscopy of benzene derivatives
  • Allylic and benzylic reactivity

Aromaticity and Electrophilic Aromatic Substitution

  • Benzene, aromaticity, and other aromatic systems
  • Nomenclature of benzene derivatives
  • Other aromatic systems
  • Electron donating and withdrawing groups
  • Inductive vs. resonance effects; effects of substituents
  • General mechanism of electrophilic aromatic substitution
  • Halogenation, Nitration, Sulfonation, Friedel-Crafts Alkylation and Acylation

Electrophilic and Nucleophilic Aromatic Substitution

  • Directing and activating effects in electrophilic aromatic substitution
  • Use of electrophilic aromatic substitution in synthesis
  • Unreactivity of aryl and vinylic halides
  • Nucleophilic substitution of aryl halides (benzyne and addition-elimination mechanisms)

Aldehydes and Ketones - Carbonyl Addition

  • Structure and reactivity of the C=O group
  • Irreversible additions to aldehydes and ketones: Grignard reagents, NaBH4, and LiAlH4

Aldehydes and Ketones - Carbonyl Addition

  • Reversible addition reactions of aldehydes and ketones: hydration, hemiacetals, acetals
  • Use of acetals as protecting groups
  • Formation and hydrolysis of imines and enamines
  • The Wittig Alkene Synthesis
  • Reduction of aldehydes and ketones to alkanes

Chemistry of Carboxylic Acids and their Derivatives

  • Acidity of carboxylic acids
  • Preparations of carboxylic acids
  • General mechanism for interconversion of carboxylic acid derivatives
  • Introduction to the Grid of Carbonyl Love
  • Converting between carboxylic acids, acid chlorides, esters, and amides
  • Hydrolysis of nitriles

Chemistry of Carboxylic Acids and their Derivatives

  • Reduction of esters, carboxylic acids, amides, and nitriles with LiAlH4
  • Alternative methods for the synthesis and hydrolysis of esters
  • Relative reactivity of carboxylic acid derivatives
  • Reaction of carboxylic acids and derivatives with hydride reagents, Grignard reagents, and organolithium reagents
  • Preparation of ketones from carboxylic acids and derivatives
  • Reduction of esters to aldehydes (DIBAL)
  • Oxidizing ketones: The Baeyer-Villiger Oxidation
  • The complete Grid of Carbonyl Love

Introduction to carbohydrates, peptides, and proteins

  • Structure, nomenclature, and stereochemistry of carbohydrates
  • Formation of acetals, disaccharides, and polysaccharides
  • Structure of alkyl glucosides: the anomeric effect
  • Structure and synthesis of amino acids
  • The peptide bond and synthesis of peptides
  • Solid-phase peptide synthesis

Enols, Enolates, and α,β-Unsaturated Compounds

  • Acidity of C=O compounds (enolate formation)
  • Tautomerization of C=O compounds (enol formation)
  • Deuteration and racemization of α-carbons
  • Halogenation under acidic and basic conditions; the haloform reaction
  • Indtroduction to the aldol reaction: addition and condensation
  • Intramolecular and crossed aldol condensations

Enols, Enolates, and α,β-Unsaturated Compounds

  • Claisen and Dieckmann condensations
  • Hydrolysis and decarboxylation of β-keto esters
  • Alkylation of moderately basic enolate ions
  • Synthesis using aldol and Claisen reactions
  • Controlling the enolization of C=O compounds: Using lithium enolates
  • Alkylation of lithium enolates

Enols, Enolates, and α,β-Unsaturated Compounds

  • Crossed aldol and Claisen reactions
  • Formation of enolates from α-bromo esters
  • Introduction to α,β-unsaturated compounds: Nucleophilic addition
  • Addition of dialkyl cuprates
  • Kinetic (1,2) vs. thermodynamic (1,4) addition
  • The Michael reaction

Enols, Enolates, and α,β-Unsaturated Compounds

  • Robinson annulation
  • A systematic approach to organic synthesis: Retrosynthetic analysis
  • Organic synthesis using aldol, Claisen, Michael, and related reactions

Chemistry of Amines

  • Nomenclature, structure, and acid/base reactions of amines
  • Preparation of primary amines: reduction of azides and nitriles
  • Preparation of secondary and tertiary amines: reductive amination
  • Amines from conjugate addition; amines from nitrile enolates

Chemistry of Amines

  • Mannich reaction in the synthesis of natural amines
  • 1,2-rearrangements to nitrogen: Beckmann, Hofmann, and Curtius rearrangements
  • Synthesis and reactivity of aromatic amines
  • Preparation and reactivity of aryl diazonium salts
  • Using aryl diazonium salts in synthesis

Diels-Alder and Pericyclic Reactions

  • Introduction to pericyclic reactions
  • Molecular orbitals of conjugated π-electron systems
  • Diels–Alder reaction
  • Synthesis using the Diels-Alder reaction

Pericyclic Reactions

  • Other cycloaddition reactions (incl. photochemical 2+2 cycloadditions)
  • Electrocyclic reactions of conjugated dienes and trienes (thermal and photochemical)
  • Sigmatropic reactions ([1.3], [1,5], [3,3] rearrangements)
  • Summary of pericyclic selection rules

The Organic Chemistry of Life

  • Key cofactors: Thiamine, NADH, and lipoamide
  • Cholesterol biosynthesis and the role of statins
  • Fatty-acid biosynthesis
  • Polyketide biosynthesis
Criteria for evaluation Written test
Methods Classical Lecture
Language English
Study material Introduction to Strategies for Organic Synthesis, Laurie S. Starkey. JohnWiley & Sons, Hoboken,2012. 360 S., Broschur,43.90E.—ISBN 978-0470484098

Organic Chemistry, Clayden, Greeves, Warren, ISBN 978-3-642-34715-3

Organic chemistry: structure and function. Vollhardt, K. Peter C. — 5th ed. / K. Peter C. Vollhardt, Neil E. Schore. ISBN 0-7167-9949-9

Changing subject? No
Corresponding lecture in collaboration with 290OPCHIOCV18: VL Introduction to Organic Chemistry (3 ECTS) equivalent to
BCBPOVOORCH: VO Organic Chemistry 1 (5,2 ECTS)
On-site course
Maximum number of participants -
Assignment procedure Direct assignment