CHEMISTRY 213 

Organic Chemistry I

An introduction to the subject of organic chemistry through a study of the characteristic reactions of the common functional groups. Study of the chemistry of the alkanes, alkenes, alkynes is continued from first year. Alkyl halides, alcohols, aldehydes and ketones, carbohydrates and ethers are also discussed. Particular emphasis is placed on the study of reaction mechanisms, and the importance of stereochemistry is stressed throughout the course.The laboratory component of the course complements the lecture material and gives students experience in using some of the basic techniques that are employed in modern chemistry laboratories. This course is required for students pursuing careers in chemistry, biology, biochemistry, home economics, forestry, pre-medicine and pharmaceutical science.

CHEM 113 and 114

Course content varies by instructor. An example of course content might be:

Alkanes and Cycloalkanes:

• Reactions of alkanes: free radical chlorination and bromination: reactivity and selectivity, free radical stability. with mechanism using single barb arrows (fishhooks).
• Natural sources of alkanes and the importance of the petroleum industry.
• Cycloalkanes (nomenclature, stability of cycloalkanes, C3-C6: Baeyer ring strain theory, H data, orbital aspects, factors affecting stability. Conformations, particularly of cyclohexane and substituted cyclohexane, axial/equatorial positions, stereoisomerism, diaxial interactions, conformational analysis).

• Structure and Synthesis: some done in 114. Review Synthesis by elimination reactions:(i) dehydrohalogenation with related stereochemistry; (ii) dehydratio.
• Synthesis by partial hydrogenation of an alkyne. Reactions: Electrophilic addition and oxidation reactions (H2, X2, HX, H2O, ROH, B2H6, KMnO4, O3 epoxidation) (cont. on next page).
• Addition of radicals to alkenes: polymers - or introduction to terpenes.
• Reaction mechanisms for hydrogenation, halogenation--Markovnikov and free radical, hydration, halohydrin, hydroboration, oxidation, epoxidation with stereochemical implications.
• Applications of reactions to multi - step syntheses.

Alkynes:

• Preparation by elimination.
• Reactions: electrophilic addition, oxidation as for alkenes; and substitution using terminal alkynes, SN2 vs. E2 aspects.
• Acidity of terminal alkynes.
• Use of alkynes with alkenes in multi-step syntheses.

• Structural and stereoisomerism - a review. Chirality, enantiomerism, optical activity (including allenes), racemic modification, configuration (R, S nomenclature). Compounds with two chiral centres, meso, threo, erythro pairs. Three dimensional and Fischer structures.
• Stereochemistry of syn and anti addition to alkenes. Conformations of disubstituted cycloalkanes.
• Resolution of an amine.

• Nucleophilic substitution reactions (SN1, SN2), mechanisms, influence of changing R , Nu, L, solvent and temperature; stereochemical aspects.
• Elimination reactions E2, E1 mechanisms, Zaitsev and Hofmann products, effect of R, Nu, L, solvent and temperature; stereochemical aspects.
• Substitution vs. Elimination summary. Reactions of chiral molecules, retention, inversion, racemization of configuration.

• Preparation: SN2 attack, hydration, hydroboration, oxymercuration-demercuration, reduction of carbonyls, Grignard synthesis, diol formation,
• Reactions: oxidation, contrast of C-O and O-H bond strengths, dehydration, PX3, tosylate, oxidation. Synthesis problems (Grignards),
• Use of alcohols in multi-step syntheses.

• Nucleophilic addition reactions (McM pp 705-715); ch. 19 (omit 19.15, 19.17; 19.16 done previously).
• (Review of) nomenclature.
• Preparations (oxidation, reduction of acid chlorides, acylation). Reactions: oxidation; reduction; nucleophilic addition - Grignard, acetals, cyanohydrins; Cannizzaro reaction.

Carbohydrates:

• Classification, particularly of the aldose series.
• Structures of monosaccharides (Fischer, Haworth, and chair forms, as applicable).
• Mutarotation. Di- and polysaccharides (sucrose, maltose, lactose, starch, cellulose), particularly their structures, linkages, and major properties. Reactions of aldoses and ketoses (particularly glucose and fructose) -oxidation, reduction, osazone formation, Kiliani-Fischer and Ruff reaction series. [If incomplete in 213, continue Carbohydrates in 214].

Ethers:

• Nomenclature and structures.
• Preparation: substitution by alkoxy ions, Williamson synthesis, alkoxymercuration.
• Reactions - cleavage by acid, use as solvents, epoxides - (recall trans diol formation in alkenes section) formation of epoxides and ring opening.

1. Distillation and the Purity of Liquids (Refractive Index);
2. The Purity of Solids: Melting Point and Mixed Melting Point;
3. Purification of Solids by Crystallization;
4. Extraction;
5. Reactions of Carbonyls: a) Qualitative Characterization of Aldehydes and Ketones; b) Identification by 2,4-dinitrophenyl hydrazone and Semicarbazone Derivatives;
6. Nucleophilic Substitution: Effect of Leaving Group on Adamantyl Halide
7. Solvolysis;
8. Synthesis of an Alkene (cyclohexene, by Dehydration of Cyclohexanol);
9. Synthesis of an Alkyl Halide (1-Bromobutane from n-Butanol);
10. Gas Chromatography: Analysis of a Mixture of Alkenes;
11. Synthesis of an Alcohol (Triphenyl Methanol, via Grignard Reagent);