Pensum/læringskrav

I tillegg til lærebok-kapitlene som er angitt nedenfor (kap. 1 og 2 forutsettes kjent fra før), er laboratoriekurset pensum.

Kompendiet for laboratoriekurset legges ut i Classfronter-rommet. Ytterligere informasjon vil bli gitt som meldinger på emnets semestersider.

For studenter som tar KJM1110 (sist gitt V2017) om igjen: De avsnitt i KJM1111-pensum som er markert med rødt, er ikke KJM1110-pensum.

Kap. 1 (Structure and Bonding) og 2 (Polar Covalent Bonds; Acids and Bases) forutsettes kjent fra før, og bør repeteres av studentene selv ved semesterstart. Oppgaveløsing (bruk e-læringsressursene!) anbefales på det varmeste.

Kap. 3 Organic Compounds: Alkanes and Their Stereochemistry

• 3.1. Functional groups
• 3.2. Alkanes and alkane isomers
• 3.3. Alkyl groups
• 3.4. Naming alkanes
• 3.5. Properties of alkanes
• 3.6. Conformations of ethane
• 3.7. Conformations of other alkanes

Kap. 4 Organic Compounds: Cycloalkanes and Their Stereochemistry

• 4.1. Naming cycloalkanes
• 4.2. Cis-trans isomerism in cycloalkanes
• 4.3. Stability of cycloalkanes: Ring strain
• 4.4. Conformations of cycloalkanes
• 4.5. Conformations of cyclohexane
• 4.6. Axial and equatorial bonds in cyclohexane
• 4.7. Conformations of monosubstituted cyclohexanes
• 4.8. Conformations of disubstituted cyclohexanes
• 4.9. Conformations of polycyclic molecules

Kap. 5 Stereochemistry at Tetrahedral Centers

• 5.1. Enantiomers and the tetrahedral carbon
• 5.2. The reason for handedness in molecules: Chirality
• 5.3. Optical activity
• 5.4. Pasteur's discovery of enantiomers
• 5.5. Sequence rules for specifying configuration
• 5.6. Diastereomers
• 5.7. Meso compounds
• 5.8. Racemic mixtures and the resolution of enantiomers
• 5.9. A review of isomerism
• 5.10. Chirality at nitrogen, phosphorus and sulfur
• 5.11. Prochirality

Kap. 6 An Overview of Organic Reactions

• 6.1. Kinds of organic reactions
• 6.2. How organic reactions occur: Mechanisms
• 6.3. Radical reactions
• 6.4. Polar reactions
• 6.5. An example of a polar reaction: Addition of HBr to ethylene
• 6.6. Using curved arrows in polar reaction mechanisms
• 6.7. Describing a reaction: Equilibria, rates, and energy changes
• 6.8. Describing a reaction: Bond dissociation energies
• 6.9. Describing a reaction: Energy diagrams and transition states
• 6.10. Describing a reaction: Intermediates

Kap. 7 Alkenes: Structure and Reactivity

• 7.1. Industrial preparation and use of alkenes
• 7.2. Calculating degree of unsaturation
• 7.3. Naming alkenes
• 7.4. Cis-trans isomerism in alkenes
• 7.5. Alkene stereochemistry and the E,Z designation
• 7.6. Stability of alkenes
• 7.7. Electrophilic addition reactions of alkenes
• 7.8. Orientation of electrophilic addition: Markovnikov’s Rule
• 7.9. Carbocation structure and stability
• 7.10. The Hammond Postulate
• 7.11. Evidence for the mechanism of electrophilic additions: Carbocation rearrangements

Kap. 8 Alkenes: Reactions and Synthesis

• 8.1. Preparation of alkenes: A preview of elimination reactions
• 8.2. Halogenation of alkenes: Addition of X₂
• 8.3. Halohydrins from alkenes: Addition of HOX
• 8.5. Hydration of alkenes: Addition of H₂O by hydroboration
• 8.6. Reduction of alkenes: Hydrogenation
• 8.7. Oxidation of alkenes: Epoxidation and hydroxylation
• 8.8. Oxidation of alkenes: Cleavage to carbonyl compounds
• 8.12. Reaction stereochemistry: Addition of H₂O to an achiral alkene
• 8.13. Reaction stereochemistry: Addition of H₂O to a chiral alkene

Kap. 9 Alkynes: An Introduction to Organic Synthesis

• 9.1. Naming alkynes
• 9.2. Preparation of alkynes: Elimination reactions of dihalides
• 9.3. Reactions of alkynes: Addition of HX and X₂
• 9.4. Hydration of alkynes
• 9.5. Reduction of alkynes
• 9.6. Oxidative cleavage of alkynes
• 9.7. Alkyne acidity: Formation of acetylide anions
• 9.8. Alkylation of acetylide anions
• 9.9. An introduction to organic synthesis

Kap. 10 Organohalides

• 10.1. Names and structures of alkyl halides
• 10.2. Preparing alkyl halides from alkanes: Radical halogenation
• 10.3. Preparing alkyl halides from alkenes: Allylic bromination
• 10.4. Stability of the allyl radical: Resonance revisited
• 10.5. Preparing alkyl halides from alcohols
• 10.6. Reactions of alkyl halides: Grignard reagents
• 10.8. Oxidation and reduction in organic chemistry

Kap. 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

• 11.1. The discovery of nucleophilic substitution reactions
• 11.2. The S_N2 reaction
• 11.3. Characteristics of the S_N2 reaction
• 11.4. The S_N1 reaction
• 11.5. Characteristics of the S_N1 reaction
• 11.7. Elimination reactions: Zaitzev's rule
• 11.8. The E2 reaction and the deuterium isotope effect
• 11.9. The E2 reaction and cyclohexane conformation
• 11.10. The E1 and E1cB reactions
• 11.12. A summary of reactivity: S_N1, S_N2, E1, E1cB, and E2

Kap. 12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy

• 12.5. Spectroscopy and the electromagnetic spectrum
• 12.6. Infrared spectroscopy
• 12.7. Interpreting infrared spectra

Kap. 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy

• 13.1. Nuclear magnetic resonance spectroscopy
• 13.2. The nature of NMR absorptions
• 13.3. The chemical shift
• 13.4. Chemical shifts in ¹H NMR spectroscopy
• 13.5. Integration of ¹H NMR absorptions: Proton counting
• 13.6. Spin-spin splitting in ¹H NMR spectra
• 13.9. Uses of ¹H NMR spectroscopy

Kap. 15 Benzene and Aromaticity

• 15.1. Naming aromatic compounds
• 15.2. Structure and stability of benzene
• 15.3. Aromaticity and the Hückel 4n+2 rule
• 15.4. Aromatic ions
• 15.5. Aromatic heterocycles: Pyridine and pyrrole
• 15.6. Polycyclic aromatic compounds

Kap. 16 Chemistry of Benzene: Electrophilic Aromatic Substitution

• 16.1. Electrophilic aromatic substitution reactions: Bromination
• 16.2. Other aromatic substitutions
• 16.3. Alkylation and acylation of aromatic rings: The Friedel-Crafts reaction
• 16.4. Substituent effects in electrophilic substitutions
• 16.5. Trisubstituted benzenes: Additivity of effects
• 16.8. Oxidation of aromatic compounds
• 16.9. Reduction of aromatic compounds
• 16.10. Synthesis of polysubstituted benzenes

Kap. 17 Alcohols and Phenols

• 17.1. Naming alcohols and phenols
• 17.2. Properties of alcohols and phenols
• 17.3. Preparation of alcohols: A review
• 17.4. Alcohols from carbonyl compounds: Reduction
• 17.5. Alcohols from carbonyl compounds: Grignard reaction
• 17.6. Reactions of alcohols
• 17.7. Oxidation of alcohols

A Preview of Carbonyl Compounds, s.595-603

Kap. 19 Aldehydes and Ketones: Nucleophilic Addition Reactions

• 19.1. Naming aldehydes and ketones
• 19.2. Preparation of aldehydes and ketones
• 19.3. Oxidation of aldehydes and ketones
• 19.4. Nucleophilic addition reactions of aldehydes and ketones
• 19.5. Nucleophilic addition of H₂O: Hydration
• 19.7. Nucleophilic addition of hydride and Grignard: Alcohol formation
• 19.8. Nucleophilic addition of amines: Imine and enamine formation (avsnittet er pensum for KJM1111, men ikke for KJM1110)
• 19.10. Nucleophilic addition of alcohols: Acetal formation
• 19.11. Nucleophilic addition of phosphorus ylides: The Wittig reaction

Kap. 20 Carbocylic Acids and Nitriles

• 20.1. Naming carboxylic acids and nitriles
• 20.2. Structure and properties of carboxylic acids
• 20.3. Biological acids and the Henderson-Hasselbalch equation
• 20.4. Substituent effects on acidity
• 20.5. Preparing carboxylic acids
• 20.6. Reactions of carboxylic acids: An overview
• 20.7. Chemistry of nitriles

Kap. 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

• 21.1. Naming carboxylic acid derivatives
• 21.2. Nucleophilic acyl substitution reactions
• 21.3. Reactions of carboxylic acids
• 21.4. Chemistry of acid halides
• 21.5. Chemistry of acid anhydrides
• 21.6. Chemistry of esters
• 21.7. Chemistry of amides
• 21.9. Polyamides and polyesters: Step-growth polymers

Kap. 22 Carbonyl Alpha-Substitution Reactions (avsnittene fra dette kapitlet er pensum for KJM1111, men ikke for KJM1110)

• 22.1. Keto-enol tautomerism
• 22.2. Reactivity of enols: Alpha-substitution reactions
• 23.3. Alpha halogenation of aldehydes and ketones
• 24.5. Acidity of alpha hydrogen atoms: Enolate ion formation
• 22.6. Reactivity of enolate ions
• 22.7. Alkylation of enolate ions

Kap. 23 Carbonyl Condensation Reactions (avsnittene fra dette kapitlet er pensum for KJM1111, men ikke for KJM1110)

• 23.1. Carbonyl condensation: The aldol reaction
• 23.2. Carbonyl condensation versus alpha substitutions
• 23.3. Dehydration of aldol products: Synthesis of enones
• 23.4. Using aldol reactions in synthesis
• 23.5. Mixed aldol reactions
• 23.6. Intramolecular aldol reactions

Kap. 24 Amines and Heterocycles

• 24.1. Naming amines
• 24.2. Structure and properties of amines
• 24.3. Basicity of amines
• 24.4. Basicity of substituted arylamines
• 24.5. Biological amines and the Henderson-Hasselbalch equation
• 24.6. Synthesis of amines (til og med s. 800) (avsnittet er pensum for KJM1111, men ikke for KJM1110)