KJM1110 - V?r 2014

Pensum/l?ringskrav

Paula Y. Bruice: Organic Chemistry, 7th Edition, 2014. Pearson. ISBN: 9781783990146.

Andre l?rebok-utgaver av samme forfatter anbefales overhodet ikke. De studenter som ikke f?lger denne anbefalingen gj?r dette helt p? eget ansvar og vil p?f?re seg selv vesentlig ekstraarbeide med selv ? m?tte definere pensumlisten!

I tillegg til l?rebok-kapitlene som er angitt nedenfor (kap. 1 og 2 forutsettes i hovedsak kjent fra f?r), er laboratoriekurset pensum.

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

Kap. 1 og 2 forutsettes i hovedsak kjent fra f?r, men vil bli grundig gjennomg?tt i starten av semesteret.

Kap. 3 An Introduction to Organic Compounds

3.1. How alkyl substituents are named
3.2. The nomenclature of alkanes
3.3. The nomenclature of cycloalkanes – skeletal structures
3.4. The nomenclature of alkyl halides
3.5. The nomenclature of ethers
3.6. The nomenclature of alcohols
3.7. The nomenclature of amines
3.8. The structures of alkyl halides, alcohols, ethers, and amines
3.9. The physical properties of alkanes, alkyl halides, alcohols, ethers, and amines
3.10. Rotation occurs about carbon-carbon single bonds
3.11. Some cycloalkanes have angle strain
3.12. Conformers of cyclohexane
3.13. Conformers of monosubstituted cyclohexanes
3.14. Conformers of disubstituted cyclohexanes
3.15. Fused cyclohexane rings

Kap. 4 Isomers – The Arrangement of Atoms in Space

4.1. Cis-trans isomers result from restricted rotation
4.2. A chiral object has a nonsuperimposable mirror image
4.3. An asymmetric center is a cause of chirality in a molecule
4.4. Isomers with one asymmetric center
4.5. Asymmetric centers and stereocenters
4.6. How to draw enantiomers
4.7. Naming enantiomers by the R,S system
4.8. Chiral compounds are optically active
4.9. How specific rotation is measured
4.10. Enantiomeric excess
4.11. Compounds with more than one asymmetric center
4.12. Stereoisomers of cyclic compounds
4.13. Meso compounds have asymmetric centers but are optically inactive
4.14. How to name isomers with more than one asymmetric center
4.15. How enantiomers can be separated
4.16. Nitrogen and phosphorous atoms can be asymmetric centers

Kap. 5 Alkenes

5.1. Molecular formulas and the degree of unsaturation
5.2. The nomenclature of alkenes
5.3. The structures of alkenes
5.4. Naming alkenes using the E,Z system
5.5. How an organic compound reacts depends on its functional group
5.6. How alkenes react: Curved arrows show the flow of electrons
5.7. Thermodynamics and kinetics
5.8. The rate of a chemical reaction
5.9. The difference between the rate of a reaction and the rate constant of a reaction
5.10. A reaction coordinate diagram describes the energy changes that take place during a reaction
5.11. Catalysis
5.12. Catalysis by enzymes

Kap. 6 The Reactions of Alkenes – The Stereochemistry of Addition Reactions

6.1. The addition of a hydrogen halide to an alkene
6.2. Carbocation stability depends on the number of alkyl groups attached to the positively charged carbon
6.3. What does the structure of the transition state look like?
6.4. Electrophilic addition reactions are regioselective
6.5. The addition of water to an alkene
6.6. The addition of an alcohol to an alkene
6.7. A carbocation will rearrange if it can form a more stable carbocation
6.8. The addition of borane to an alkene: Hydroboration-oxidation
6.9. The addition of a halogen to an alkene
6.10. The addition of a peroxyacid to an alkene
6.11. The addition of ozone to an alkene: Ozonolysis
6.12. The addition of hydrogen to an alkene
6.13. The relative stabilities of alkenes
6.14. Regioselective, stereoselective, and stereospecific reactions
6.15. The stereochemistry of electrophilic addition reactions of alkenes
6.18. Reactions and synthesis

Kap. 7 The Reactions of Alkynes

7.1. The nomenclature of alkynes
7.2. How to name a compound that has more than one functional group
7.3. The physical properties of unsaturated hydrocarbons
7.4. The structure of alkynes
7.5. Alkynes are less reactive than alkenes
7.6. The addition of hydrogen halides and the addition of halogens to an alkyne
7.7. The addition of water to an alkyne
7.8. The addition of borane to an alkyne: Hydroboration-oxidation
7.9. The addition of hydrogen to an alkyne
7.10. A hydrogen bonded to an sp carbon is “acidic”
7.11. Synthesis using acetylide ions
7.12. Designing a synthesis: An introduction to multistep synthesis

Kap. 8 Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction

8.1. Delocalized electrons explain benzene’s structure
8.2. The bonding in benzene
8.3. Resonance contributors and the resonance hybrid
8.4. How to draw resonance contributors
8.5. The predicted stabilities of resonance contributors
8.6. Delocalization energy is the additional stability delocalized electrons give to a compound
8.7. Benzene is an aromatic compound
8.8. The two criteria for aromaticity
8.9. Applying the criteria for aromaticity
8.10. Aromatic heterocyclic compounds
8.11. Antiaromaticity
8.13. More examples that show how delocalized electrons increase stability
8.15. How delocalized electrons affect pKa values
8.16. Delocalized electrons can affect the product of a reaction

Kap. 9 Substitution Reactions of Alkyl Halides

9.1. The mechanism for an SN2 reaction
9.2. Factors that affect SN2 reactions
9.3. The mechanism for an SN1 reaction
9.4. Factors that affect SN1 reactions
9.5. Benzyl halides, allylic halides, vinylic halides, and aryl halides
9.6. Competition between SN2 and SN1 reactions
9.7. The role of the solvent in SN2 and SN1 reactions
9.8. Intermolecular versus intramolecular reactions

Kap. 10 Elimination Reactions of Alkyl Halides – Competition Between Substitution and Elimination

10.1. The E2 reaction
10.2. An E2 reaction is regioselective
10.3. The E1 reaction
10.4. Benzylic and allylic halides
10.5. Competition between E2 and E1 reactions
10.6. E2 and E1 reactions are stereoselective
10.7. Elimination of substituted cyclohexanes
10.9 Co.mpetition between substitution and elimination
10.10. Substitution and elimination reactions in synthesis
10.11. Designing a synthesis II: Approaching the problem

Kap. 11 Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols

11.1. Nucleophilic substitution reactions of alcohols: Forming alkyl halides
11.2. Other methods used to convert alcohols into alkyl halides
11.3. Converting an alcohol into a sulfonate ester
11.4. Elimination reactions of alcohols: Dehydration
11.5. Oxidation of alcohols
11.6. Nucleophilic substitution reactions of ethers
11.7. Nucleophilic substitution reactions of epoxides

Kap. 12 Organometallic Compounds

12.1. Organolitium and organomagnesium compounds

Kap. 13 Radicals – Reactions of Alkanes

13.1. Alkanes are unreactive compounds
13.2. The chlorination and bromination of alkanes
13.3. Radical stability depends on the number of alkyl groups attached
13.9. Radical substitution of benzylic and allylic hydrogens

Kap. 14 Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet/Visible Spectroscopy

14.1. Mass spectrometry
14.2. The mass spectrum. Fragmentation
14.3. Using the m/z value of the molecular ion to calculate the molecular formula

Kap. 15 NMR spectroscopy

15.1. An introduction to NMR spectroscopy
15.2. Fourier Transform NMR
15.3. Shielding causes different hydrogens to show signals at different frequencies
15.4. The number of signals in an 1H NMR spectrum
15.5. The chemical shift tells how far the signal is from the reference signal
15.6. The relative positions of 1H NMR signals
15.7. The characteristic values of chemical shifts
15.8. Diamagnetic anisotropy
15.9. The integration of NMR signals reveals the relative number of protons causing each signal
15.10. The splitting of the signals is described by the N+1 rule
15.11. What causes splitting?
15.20. 13C NMR spectroscopy

Kap. 16 Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

16.1. Nomenclature of carboxylic acids and carboxylic acid derivatives
16.2. The structures of carboxylic acids and carboxylic acid derivatives
16.3. The physical properties of carbonyl compounds
16.5. How carboxylic acids and carboxylic acid derivatives react
16.6. The relative reactivities of carboxylic acids and carboxylic acid derivatives
16.7. The general mechanism for nucleophilic addition-elimination reactions
16.8. The reactions of acyl chlorides
16.9. The reactions of esters
16.10. Acid-catalyzed ester hydrolysis and transesterification
16.11. Hydroxide-ion-promoted ester hydrolysis
16.12. How the mechanism for nucleophilic addition-elimination was confirmed
16.14. Reactions of carboxylic acids
16.15. Reactions of amides
16.16. Acid-catalyzed amide hydrolysis and alcoholysis
16.17. Hydroxide-ion-promoted hydrolysis of amides
16.19. Nitriles
16.20. Acid anhydrides
16.21. Dicarboxylic acids
16.22. How chemists activate carboxylic acids

Kap. 17 Reactions of Aldehydes and Ketones. More Reactions of Carboxylic Acid Derivatives. Reactions of a,b-Unsaturated Carbonyl Compounds

17.1. The nomenclature of aldehydes and ketones
17.2. The relative reactivities of carbonyl compounds
17.3. How aldehydes and ketones react
17.4. The reactions of carbonyl compounds with Grignard reagents
17.5. The reactions of carbonyl compounds with acetylide ions
17.7. The reactions of carbonyl compounds with hydride ion
17.8. More about reduction reactions
17.9. Chemoselective reactions
17.11. The reactions of aldehydes and ketones with water
17.12. The reactions of aldehydes and ketones with alcohols
17.16. The Wittig reaction forms an alkene

Kap. 19 Reactions of Benzene and Substituted Benzenes

19.1. The nomenclature of monosubstituted benzenes
19.2. How benzene reacts
19.3. The general mechanism for electrophilic aromatic substitution reactions
19.4. The halogenation of benzene
19.5. The nitration of benzene
19.6. The sulfonation of benzene
19.7. The Friedel-Crafts acylation of benzene
19.8. The Friedel-Crafts alkylation of benzene
19.9. The alkylation of benzene by acylation-reduction
19.12 How some substituents on a benzene ring can be chemically changed
19.13 The nomenclature of disubstituted and polysubstituted benzenes
19.14 The effect of substituents on reactivity
19.15 The effect of substituents on orientation
19.16 The effect of substituents on pKa
19.17 The ortho-para ratio
19.18 Additional considerations regarding substituent effects
19.19 Designing a synthesis: Synthesis of monosubstituted and disubstituted benzenes
19.20 Synthesis of trisubstituted benzenes

Kap. 20 More About Amines – Reactions of Heterocyclic Compounds

20.1. More about amine nomenclature
20.2. More about the acid-base properties of amines
20.5. Aromatic five-membered-ring heterocycles (2 f?rste sider)
20.6. Aromatic six-membered-ring heterocycles (2 f?rste sider)

Totalt ca. 410 sider

Publisert 16. des. 2013 14:56 - Sist endret 24. feb. 2014 20:59