[ 290OPCHOC1V18 ] VL (*)Organic Chemistry 1

Es ist eine neuere Version 2023W dieser LV im Curriculum Bachelorstudium Naturwissenschaftliche Grundlagen der Technik (NaWi-Tec) 2023W vorhanden.
(*) Leider ist diese Information in Deutsch nicht verfügbar.
Workload Ausbildungslevel Studienfachbereich VerantwortlicheR Semesterstunden Anbietende Uni
4,5 ECTS B1 - Bachelor 1. Jahr Chemie Norbert Müller 3 SSt Johannes Kepler Universität Linz
Quellcurriculum Bachelorstudium Chemistry 2018W
Ziele (*)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
Lehrinhalte (*)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
  • Introduction 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
Beurteilungskriterien (*)Positive Evaluation of the final written exam.
Lehrmethoden (*)A combination of powerpoint (as well as handouts for the students) and specific examples and details written on the blackboard.
Abhaltungssprache Englisch
Literatur (*)
  • 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

Lehrinhalte wechselnd? Nein
Äquivalenzen (*)in collaboration with 290OPCHIOCV18: VL Introduction to Organic Chemistry (3 ECTS) equivalent to
TCBPCVOORC1: VO Organische Chemie I (5,2 ECTS)
Teilungsziffer -
Zuteilungsverfahren Direktzuteilung