Organic Chemistry II
The chemistry of aromatic compounds, alcohols, ethers, carbonyl compounds and amines: conjugated dienes, their Hückel molecular orbitals, kinetic and thermodynamic addition and the Diels–Alder reaction with its endo rule, and UV-visible absorption with the Woodward–Fieser rules; the structure and resonance energy of benzene, Hückel's rule, Frost circles, aromatic ions, heterocycles and fused rings; electrophilic aromatic substitution by halogenation, nitration, sulfonation and Friedel–Crafts alkylation and acylation, activating and deactivating groups, ortho, para and meta direction, partial rate factors, nucleophilic aromatic substitution and the Hammett equation; the acidity of alcohols and phenols, hydride reductions, Grignard additions and the oxidation of alcohols; the Williamson ether synthesis, ether cleavage and peroxides, crown ethers, the regiochemistry of epoxide opening and the chemistry of thiols and sulfides; nucleophilic addition to aldehydes and ketones giving hydrates, acetals as protecting groups, imines, enamines and cyanohydrins, with the Wittig reaction and reductions to CH₂; keto–enol tautomerism, α-hydrogen acidity, kinetic and thermodynamic enolates, α-halogenation and the haloform reaction, and enolate, malonic and acetoacetic ester alkylation; aldol reactions and condensations, the Michael reaction, the Robinson annulation and the Claisen and Dieckmann condensations; carboxylic acid acidity and nucleophilic acyl substitution of acid chlorides, anhydrides, esters, amides and nitriles, Fischer esterification, saponification and step-growth polymers; the basicity, preparation and reactions of amines and diazonium salts; and a capstone on retrosynthetic analysis and the planning of multistep syntheses of flavour, fragrance, pheromone and polymer targets.
CHEM-263 Year 2 3 credits 12 lessons · 5 h 1 min ▶ Video lessons coming soon
Offered by HSM University · Chemistry
This is the Canadian version of this course. See the American version.
What you'll learn
- Identify the functional groups of aromatic compounds, alcohols, ethers, carbonyl compounds and amines in everyday molecules, and explain the electrophilic carbonyl carbon, the acidic α-hydrogen, aromaticity and lone-pair basicity as the organizing ideas of the course.
- Explain conjugation with resonance and Hückel molecular orbitals, predict kinetic and thermodynamic products of addition to dienes, predict the products and stereochemistry of Diels–Alder reactions, and estimate UV-visible absorption with the Woodward–Fieser rules.
- Apply Hückel's rule and Frost circles to classify rings and ions as aromatic, antiaromatic or nonaromatic, use heats of hydrogenation to measure aromatic stabilization, and explain the basicity of aromatic heterocycles.
- Write the mechanism of electrophilic aromatic substitution, describe halogenation, nitration, sulfonation and Friedel–Crafts reactions, predict the effects of substituents on rate and orientation, and plan syntheses of substituted benzenes.
- Explain the properties and acidity of alcohols and phenols, prepare alcohols by hydride reduction and Grignard addition, and predict the products of alcohol oxidation using carbon oxidation numbers.
- Prepare ethers by the Williamson synthesis, predict the regiochemistry and stereochemistry of epoxide ring opening under acidic and basic conditions, and compare thiols and sulfides with their oxygen analogues.
- Describe nucleophilic addition to aldehydes and ketones, including hydrates, acetals as protecting groups, imines, enamines, cyanohydrins, the Wittig reaction and reductions to CH₂, and relate equilibrium constants to structure.
- Explain keto–enol tautomerism and the acidity of α-hydrogens, choose bases and conditions to form kinetic or thermodynamic enolates, and predict the products of α-halogenation, enolate alkylation and the malonic and acetoacetic ester syntheses.
- Write mechanisms for the aldol reaction and condensation, crossed and intramolecular aldols, the Michael reaction, the Robinson annulation and the Claisen and Dieckmann condensations, and explain what drives each.
- Explain the acidity of carboxylic acids, apply the mechanism and reactivity order of nucleophilic acyl substitution, calculate Fischer esterification equilibria, and describe esters, amides, nitriles and step-growth polymers.
- Rank the basicity of amines and nitrogen heterocycles from structure, separate amines by extraction, prepare amines without overalkylation, and use diazonium salts in Sandmeyer and azo coupling reactions.
- Plan multistep syntheses by retrosynthetic analysis, choosing disconnections, step order and protecting groups, and compare routes by overall yield, convergence and atom economy.
Course content
12 lessons · 5 h 1 min total · final exam
- 1 Why carbonyls and aromatics: the chemistry of everyday molecules 24 min · quiz
- 2 Conjugation, resonance and dienes: the Diels–Alder reaction and UV-visible absorption 26 min · quiz
- 3 Aromaticity: benzene, Hückel's rule and aromatic ions 26 min · quiz
- 4 Electrophilic aromatic substitution and substituent effects 25 min · quiz
- 5 Alcohols: properties, preparation and oxidation 26 min · quiz
- 6 Ethers, epoxides and sulfur analogues 28 min · quiz
- 7 Aldehydes and ketones: nucleophilic addition 24 min · quiz
- 8 Enols and enolates: alpha substitution 23 min · quiz
- 9 Carbonyl condensations: aldol and Claisen reactions 24 min · quiz
- 10 Carboxylic acids and their derivatives: nucleophilic acyl substitution 24 min · quiz
- 11 Amines: basicity, preparation and reactions 25 min · quiz
- 12 Capstone: multistep synthesis and retrosynthetic planning 26 min · quiz
- E Final exam 20 questions
Requirements
Recommended background. You can start any course at any time.
Description
The chemistry of aromatic compounds, alcohols, ethers, carbonyl compounds and amines: conjugated dienes, their Hückel molecular orbitals, kinetic and thermodynamic addition and the Diels–Alder reaction with its endo rule, and UV-visible absorption with the Woodward–Fieser rules; the structure and resonance energy of benzene, Hückel's rule, Frost circles, aromatic ions, heterocycles and fused rings; electrophilic aromatic substitution by halogenation, nitration, sulfonation and Friedel–Crafts alkylation and acylation, activating and deactivating groups, ortho, para and meta direction, partial rate factors, nucleophilic aromatic substitution and the Hammett equation; the acidity of alcohols and phenols, hydride reductions, Grignard additions and the oxidation of alcohols; the Williamson ether synthesis, ether cleavage and peroxides, crown ethers, the regiochemistry of epoxide opening and the chemistry of thiols and sulfides; nucleophilic addition to aldehydes and ketones giving hydrates, acetals as protecting groups, imines, enamines and cyanohydrins, with the Wittig reaction and reductions to CH₂; keto–enol tautomerism, α-hydrogen acidity, kinetic and thermodynamic enolates, α-halogenation and the haloform reaction, and enolate, malonic and acetoacetic ester alkylation; aldol reactions and condensations, the Michael reaction, the Robinson annulation and the Claisen and Dieckmann condensations; carboxylic acid acidity and nucleophilic acyl substitution of acid chlorides, anhydrides, esters, amides and nitriles, Fischer esterification, saponification and step-growth polymers; the basicity, preparation and reactions of amines and diazonium salts; and a capstone on retrosynthetic analysis and the planning of multistep syntheses of flavour, fragrance, pheromone and polymer targets.
Part of the Science stream, typically taken in year 2.