KJM1110 - Høst 2012

Pensum/læringskrav

John E. McMurry: Organic Chemistry, 8th Edition, 2011. Thomson, Brooks/Cole. ISBN: 0-8400-5453-X.

Andre lærebok-utgaver av samme forfatter anbefales overhodet ikke. De studenter som ikke følger denne anbefalingen gjør dette helt på eget ansvar og vil påføre seg selv vesentlig ekstraarbeide!

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

Kompendiet for laboratoriekurset vil være til salgs hos Akademika, tidspunktet vil annonseres senere. Ytterligere informasjon vil bli gitt som meldinger på emnets semestersider og i Classfronter-rommet.

Kap. 1 og 2 forutsettes i hovedsak kjent fra før

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
8.4. Hydration of alkenes: Addition of H2O by oxymercuration
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 properties 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 SN2 reaction
11.3. Characteristics of the SN2 reaction
11.4. The SN1 reaction
11.5. Characteristics of the SN1 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: SN1, SN2, E1, E1cB, and E2

Kap. 12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy

12.1. Mass spectrometry of small molecules: Magnetic-sector instruments
12.2. Interpreting mass spectra

Kap. 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy

13.1. Nuclear magnetic resonance spectroscopy
13.2. The nature of NMR absorptions
13.3. Chemical shifts
13.5. Characteristics of 13C NMR spectroscopy
13.9. Chemical shifts in 1H NMR spectroscopy
13.10. Integration of 1H NMR absorptions: Proton counting
13.11. Spin-spin splitting in 1H NMR spectra
13.13. Uses of 1H NMR spectroscopy

Kap. 15 Benzene and Aromaticity

15.1. Sources and names of aromatic compounds
15.2. Structure and stability of benzene: Molecular orbital theory
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. An explanation of substituent effects
16.6. Trisubstituted benzenes: Additivity of effects
16.9. Oxidation of aromatic compounds
16.10. Reduction of aromatic compounds
16.11. Synthesis of trisubstituted 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.712-717

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 Grignard and hydride reagents: Alcohol formation
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. Nucleophilic acyl substitution 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. 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

Totalt 426 sider

Publisert 21. mars 2012 08:49 - Sist endret 14. aug. 2012 12:54