CHEM1280 Introduction to Organic Chemistry and Biomolecules
2020-2021 2nd Term
Course Description:
This course provides an overview of organic functional groups that constitute biomolecules.
Under themes of common interests and practical importance, this course will provide students with
basic principles of organic chemistry to understand the formation, structures and chemical
properties of biomolecules.
Selected fundamental concepts in chemical bonding and
stereochemistry relevant to biomolecules will be highlighted.
Teaching mode: Online via Zoom starting from 11 Jan. 2021 unless the University makes
announcement to change teaching mode when conditions of COVID-19 pandemic in Hong Kong
improve.
Zoom Meeting：CHEM1280
https://cuhk.zoom.us/j/96273602219?pwd=cE5xZlQrY3FxbW96MmxONGtheHhTUT09
Meeting ID: 962 7360 2219
Passcode: 745933
Lectures: 2:30 – 4:15 pm every Monday and 11:30 am – 12:15 pm every Thursday
Tutorial: 12:30 – 13:15 pm every Thursday
Office hour: 4:15 – 5:00 pm every Monday (at the same Zoom meeting room)
Instructor:
Teaching assistants:
Prof. MIAO Qian (繆 謙)
Ms. CHEUNG Ka Man, Ms. WANG Yujing, Ms. XIONG Yongming
Assessments:
Homework (10%); Midterm exam (30%); Final exam (60%)
Methods for exam:
Plan A if COVID-19 pandemic is under control: face-to-face and close-book
Plan B if face-to-face assessment is not possible due to the pandemic: online and open-book
Textbook:
Bruice, P.Y.: Essential Organic Chemistry, Global Edition, Pearson Education 2015
(E-book available through the CUHK library website: https://ebookcentral.proquest.com/lib/cuhkebooks/detail.action?pq-origsite=primo&docID=5174783)
References:
1) Paula Y. Bruice, Organic Chemistry, 8th Ed. (Global Ed.), Pearson Education, 2017
(E-book: https://ebookcentral.proquest.com/lib/cuhk-ebooks/reader.action?docID=5185922&ppg=1)
2) John E. McMurry, Organic Chemistry, 9th Ed. Boston, MA: Cengage Learning, 2015
(E-book: https://ebookcentral.proquest.com/lib/cuhk-ebooks/detail.action?docID=4787779)
Course Contents:
1. Basic Building Blocks for Life: Covalent Bonding and Functional Groups
This section introduces how the atoms that compose the majority of living organism (C, H,
O, N) join together to form the simple molecules that are the basic building blocks of life.
(11 weeks)
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Covalent bonding of carbon
• A brief history of modern atomic theory
• Why carbon instead of silicon for life?
Organic acids and bases: more than sour and bitter molecules
Introduction of organic compounds
• Overview of functional groups and naming compounds
• Distillation of crude oil: alkane family and physical properties
Alkenes and alkynes
• Ethanol from ethylene: electrophilic addition reaction
• Plastics from alkenes: polymers and chain-growth polymerization
• Trans fat: cis-trans isomers and hydrogenation reaction of alkenes
Resonance, delocalized electrons and aromaticity
• Where does the extra stability of 1,3-butadiene come from?
• Why carrots are orange?
• The puzzle of benzene structure and aromaticity
• Two Nobel prizes for carbon: fullerenes and graphene
3D structures of organic molecules (conformation and chirality)
• 3D structure of cholesterol: conformations and strains
• Is nature handed? - chirality and chiral molecules
Alkyl halides: Two sides of the same coin
• From chemical weapons to cancer drugs: Nucleophilic substitution reactions of
alkyl halides
• Radical reactions, chlorofluorocarbons (CFCs) and the ozone layer
• "Silent Spring" - DDT and biological magnification
Alcohols, ethers and amines
• Breath alcohol test and reactions of alcohols
• Benzo[a]pyrene and cancer: Reactions of arene oxides
• Legal or illegal drugs: physiologically active derivatives of
2-phenylethanamine
Carbonyl compounds
• Testing glucose in urine and oxidative chemical tests for aldehydes
• Structure of sedative chloral hydrate and nucleophilic addition of carbonyl groups
• Nobel Prize in Chemistry 1912 and Grignard reagents
• The synthesis of aspirin: chemistry of enol and enolate
• From fats to soap: Nucleophilic acyl substitution reactions
2. Compounds of Life
This section introduces three classes of molecules essential to the living cell. (2 weeks)
1) Sugars and carbohydrates
• Molecular structures of sugars
• Lactose intolerance and glycosides
• Starch and cellulose
2) From amino acids to proteins
• The 20 amino acids that form proteins
• Acidic and basic properties of amino acids and MSG
• Straight or curly hair in relation to disulfide bonds
• Synthesizing peptides with a machine
3) From nucleosides to DNA and RNA
• Molecular basis of heredity
• Why does DNA not have a 2’-OH Group?
• Why does DNA have T instead of U?