| Topic |
Sub-topic |
| Lesson 1. Reactivity of organic compounds |
Organic reaction types: addition, elimination, substitution, condensation, transposition. Reaction mechanisms: concerted and stepwise reactions. Energy profile for a reaction. Kinetic and thermodynamic control. Homolytic and heterolytic cleavage: radical and ionic reactions. Reaction intermediates: free radicals, carbocations and carbanions. Structure and stability. Reagent types: acids/bases, oxidizing/reducing agents, electrophiles/nucleophiles. |
| Lesson 2. Structure and reactivity of functional groups |
Configurational stereoisomerism. Alkanes and cycloalkanes. Organic compounds with single bond carbon-heteroatom (nitrogen, oxygen, halogens, metals, sulfur) functional groups. Acidity and basicity of amines and alcohols. |
| Lesson 3. Addition reactions to multiple carbon-carbon bonds |
Structure and reactivity of functional groups with multiple carbon-carbon bonds: alkenes, alkynes and conjugated dienes. Acidity of terminal alkynes. Catalytic hydrogenation of alkenes (heat of hydrogenation and relative stability of alkenes and dienes). Electrophilic addition to alkenes: addition of hydrogen halides: regioselectivity; electrophilic hydration: regioselectivity and stereochemistry; addition of halogens; dihydroxylation. Addition reactions of alkynes. Electrophilic addition to conjugated dienes.
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| Lesson 4. Aromatic substitution reactions |
Structure and reactivity of aromatic compounds. General mechanism for electrophilic aromatic substitution reactions. Electrophilic aromatic substitution reactions: halogenation, nitration, sulfonation, and Friedel-Crafts alkylation and acylation. Electrophilic aromatic substitution in substituted benzenes: orientation and reactivity. Electrophilic aromatic substitution in phenols and aromatic amines. Arenediazonium salts. Nucleophilic aromatic substitution reactions.
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| Lesson 5. Nucleophilic addition to carbonyl compounds |
Structure and general reactivity of the carbonyl group (aldehydes and ketones). Keto-enol tautomerism. General mechanism for the nucleophilic addition reaction. Irreversible nucleophilic additions: addition of organometallic compounds (alkynyl anions, alkyllithium and alkylmagnesium reagents), addition of phosphorus ylides (the Wittig reaction); addition of hydrides (reduction of carbonyl compounds to alcohols). Reversible nucleophilic additions: addition of water, alcohols and thiols; nucleophilic addition of ammonia and its derivatives; addition of hydrogen cyanide. |
| Lesson 6. Nucleophilic acyl substitution reactions in carbonyl groups |
Stucture and general reactivity of carboxylic acids and carboxylic acid derivatives. Acidity of carboxylic acids. Acidity and basicity of amides. Addition-elimination general mechanism. Relative reactivities of carboxylic acid derivatives. Hydrolysis. Esterification and transesterification reactions. Formation of amides. Reactions with organometallics. Structure and reactivity of nitriles. Hydrolisis and reactions with organometallics.
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| Experiment 1 |
Separation of a three component mixture (acetylsalicylic acid, paracetamol and caffeine) by two different methods: (a) acid-base extraction and (b) column chromatography (two sessions). |
| Experiment 2 |
Electrophilic addition to a double bond: bromation (one session). |
| Experiment 3 |
Electrophilic addition to a double bond: hydration (one session). |
| Experiment 4 |
Electrophilic aromatic substitution: nitration (one session) |
| Experiment 5 |
Ketone reduction (one session). |
| Experiment 6 |
Nucleophilic addition to a carbonyl group: Wittig synthesis (one session). |
| Experiment 7 |
Extraction of a natural ester (trimyristin) and its basic hydrolysis (two sessions). |
| Experiment 8 |
Multistep synthesis. Preparation of benzocaine from para-toluidine (four sessions). |
