Looking for something specific in this course? The compiles links to most course resources in a single page.
| Modules | Organic Materials |
| Concepts | organic chemistry nomenclature, chains, alkanes, alkenes, alkynes, aromatics, functional groups, isomers |
| Keywords | hydrocarbon, radical, sp3 orbital, sp2 orbital, sp orbital, straight chain, branched chain, saturated hydrocarbon, unsaturated hydrocarbon, methylated, conformational isomer, constitutional isomer, stereoisomer, aromatic compound, resonant hybrid structure, combustion, conductivity, IUPAC |
| Chemical Substances | carbon (C), hydrogen (H), isomers of C4H10 (butane, isobutene, 2-methyl propane), methylene radical, ethyl radical, ethyl alcohol, ethylene (aka ethane); butane (C4H8), cis-2-butene, trans-2-butene, propene, propylene, allyl, acetylene, benzene; 1,3 butadiene; gasoline |
| Applications | gasoline automobile engine knocking, octane rating |
This session assumes you’ve completed the Bonding and Molecules module (Session 7 through Session 12), in particular understanding the concepts of
This session is the first of six sessions on organic compounds. The next two sessions cover polymers, followed by three sessions applying these concepts to biochemistry.
After completing this session, you should be able to:
| Book Chapters | Topics |
|---|---|
| [Saylor] 24.1, “Functional Groups and Classes of Organic Compounds.” | Overview of five organic compound families: hydrocarbons, halogen-containing, oxygen-containing, carboxylic acid derivatives, and nitrogen-containing; common nomenclature |
| [Saylor] 24.2, “Isomers of Organic Compounds.” | Conformational isomers, structural isomers, stereoisomers |
This lecture is a single-session introduction to organic chemistry: the chemistry of hydrocarbon compounds containing both carbon (C) and hydrogen (H), plus other elements. The class begins with a review of what makes carbon special: uniquely capable of forming multiple bonds, capable of self-linking, etc. Most of the session is a survey of three types of hydrocarbons: alkanes, alkenes, and alkynes. A hydrocarbon’s properties are determined by characteristics like the type of chain (straight chains vs. branched chains), bond types (pi, double, and triple bonds), and resonance.
Naming and nomenclature conventions receive much attention. Woven throughout the lecture are discussions about:
Among the applications used for illustration, the lecture describes why acetylene is so energetic as a fuel, why graphite is a good electrical conductor, and the chemical basis of gasoline octane ratings.
No homework is assigned for this session.
As a single-session overview of organic chemistry, this class has limited scope. For instance, it does not introduce every class of organic compounds, leaving aldehydes, ketones, and esters for further study.
| Content | Provider | Level | Notes |
|---|---|---|---|
| 5.12 Organic Chemistry I | MIT OpenCourseWare | Undergraduate (second-year) | The first of a two-semester sequence on organic chemistry, taken after 3.091 or equivalent |
| Modules | Organic Materials |
| Concepts | polymer architecture, polymer composition, backbone structure, polymer material properties, natural and synthetic polymers |
| Keywords | macromolecule, -mer, monomer, polymerization index, ordered solid, disordered solid, Dalton (atomic mass unit), cooling curve, partial crystallization, homopolymer, copolymer, tacticity, stereoisomerism, isotactic, syndiotactic, atactic, conformality, covalent bridge, crosslinking, elastomer, disulfide bond |
| Chemical Substances | polyethylene (PE), low density polyethelene (LDPE), high density polyethelene (LDPE), polyvinyl chloride (PVC), acrylonitrile butadiene styrene (ABS), natural rubber |
| Applications | Manufactured products of the past 80-100 years, vulcanized rubber |
Before starting this session, you should be familiar with:
This session is the first of two devoted to polymers. The polymers sessions are prerequisites for Sessions 30-32 on biochemistry.
After completing this session, you should be able to:
| Book Chapters | Topics |
|---|---|
| [Saylor] 12.8, “Polymeric Solids.” | Overview of biological and synthetic polymers |
Polymer chemistry is an example of applied organic chemistry. Polymers are long chain macromolecules built from repeated smaller chemical structures or ‘-mers.’ They are found widely in the natural world (e.g. proteins, rubber, cellulose) and, increasingly the past century, in synthetic form (e.g. “plastics”). Polymers have been central to many technological innovations that shape the modern world, such as film that enabled the cinema, or the progression of vinyl LPs to polycarbonate CDs and DVDs that enabled recorded music and video distribution.
This lecture begins by describing some basic characteristics of polymers. A polymer’s physical properties are influenced by the degree of ordering in the molecular chains. A comparison of low-density and high-density polyethylene (LDPE and HDPE) reveals that HDPE is molecularly more ordered, with more zones of partial crystallization, and thus more dense and rigid than LDPE. As a result, LDPE is quite flexible and transparent, suited for food wrap; whereas HDPE is optically translucent and more rigid, suited for a milk jug.
The lecture describes polymer molecular architecture in terms of:
The class ends with a quick recounting of the discovery and impact of rubber vulcanization, in which difficult-to-manage raw rubber gum becomes a more useful material by heating and adding sulfide to create crosslinking.
| [saylor] Sections | Conceptual | Numerical |
|---|---|---|
| [Saylor] 24.2, “Isomers of Organic Compounds.” | 1, 3, 4, 5 | none |
| [Saylor] 24.5, “Common Classes of Organic Compounds.” | 1, 4 | none |
The Beatles. “Polythene Pam.” Abbey Road. Apple Records, 1969.
| Content | Provider | Level |
|---|---|---|
| Polymer Basics | DoITPoMS | Undergraduate |
| Modules | Organic Materials |
| Concepts | polymer synthesis by addition and condensation, polymer structure-property relationships, social and culture implications of polymers |
| Keywords | plastics, addition polymerization, radical, condensation polymerization, amide bond, carbonyl group, electrical insulator, thermoplastic, thermoset, crystallization zone, Wallace Carothers, glass transition temperature, recycling, design for environment (DFE) |
| Chemical Substances | polyester, poly(ethylene terephthalate) (PET), silicone, nylon, polyurethane, norbornene, isoprene, Bakelite |
| Applications | polypropylene in lithium ion batteries, soda bottles and fabrics, electrical insulators, recycling and packaging |
Before starting this session, you should be familiar with:
The next segment on biochemistry (Sessions 30 through 32) builds upon these introductory polymers sessions.
After completing this session, you should be able to:
| Book Chapters | Topics |
|---|---|
| [PB-OC] 28, “Synthetic Polymers.” | Addition and condensation synthesis; addition (chain growth) and condensation (step growth) polymers; stereochemistry; dienes and rubber; copolymers; structure-property relationships |
| [JS] 13.1, “Polymerization.” | Polymer form as it relates to synthesis; example of collagen |
| [JS] 13.2, “Structural Features of Polymers.” | Polymer structure as it relates to synthesis; example of rubber vulcanization |
Lecture 29: Polymers: Synthesis, Properties & Applications
This session focuses on polymer synthesis, the relationships between polymer structure and properties, and the culture implications of polymers.
The two forms of polymer synthesis (addition and condensation) are described in terms of processes, resulting chemical structures and properties, and example materials. Factors affecting recyclability are described, along with defining thermoplastic and thermoset characteristics. Crystallization zones are presented as a means for controlling a polymer’s mechanical performance.
Prof. Sadoway summarizes the properties of polymers as follows:
Polymers have had significant impact on society. The economic and performance improvements introduced by polymer-based substitute materials have transformed many aspects of modern daily life, and led to entirely new products. The class discussion ranges from early 20th century inventions (e.g. nylon, Bakelite), to the late 1960s fascination with plastics, to present-day concerns about recycling and human health impacts.
[JS] Chapter 13, Sample Problems 13.1 and 13.4
Perree, R. Bakelite: The Material of a Thousand Uses. Amsterdam, NL: Cadre, 1996. ISBN: 9789053492338.
Meikle, J. American Plastic: A Culture History. New Brunswick, NJ: Rutgers University Press, 1995. ISBN: 9780813522357.
Brown, D. E. Inventing Modern America: From the Microwave to the Mouse. Cambridge, MA: MIT Press, 2001. ISBN: 9780262523493.
Carothers, W.H. Collected Papers of Wallace Hume Carothers on High Polymeric Substances. New York, NY: Interscience Publishers, 1940. ISBN: 9781406759259. [Download or view complete work from Internet Archive]
Furukawa, Y. Inventing Polymer Science: Staudinger, Carothers, and the Emergence of Macromolecular Science. Philadelphia, PA: University of Pennsylvania Press, 1998. ISBN: 9780812233360.
“Mr. Cellophane.” Chicago. DVD. Miramax, 2003.
The Graduate. Directed by M. Nichols. DVD. MGM, 1967.
| Content | Provider | Level |
|---|---|---|
| Polymer Basics, The Glass Transition in Polymers, Crystallinity in Polymers | DoITPoMS | Undergraduate |
| 3.063 Polymer Physics | MIT OpenCourseWare | Undergraduate (elective) |
| 3.064 Polymer Engineering | MIT OpenCourseWare | Undergraduate (elective) |
| 10.467 Polymer Science Laboratory | MIT OpenCourseWare | Undergraduate (elective) / Graduate |
| 10.569 Synthesis of Polymers | MIT OpenCourseWare | Graduate |
| Introduction to Polymers | OpenUniversity UK | Masters |
| Modules | Organic Materials |
| Concepts | amino acids, peptides, proteins |
| Keywords | molecular biology, biomolecule, amino acid, polymer, protein, pH, Brønsted base, amine group, carboxylic acid, alpha carbon, substituent, hydrophilic, chirality, enantiomer, optical activity, polarized light, dextrorotatory, levorotatory, sugars, invert sugar, racemic, teratogenic, zwitterions, Henderson-Hasselbalch equation, protonation, Le Châtelier principle |
| Chemical Substances | thalidomide, Ritalin, trinitrotoluene (TNT) |
| Applications | biology, pharmaceuticals, explosives |
Before starting this session, you should be familiar with:
This is the first of three sessions on biochemistry.
After completing this session, you should be able to:
| Book Chapters | Topics |
|---|---|
| [Saylor] 12.8, “Polymeric Solids.” | Introduction to biological polymers (peptides and proteins) |
| [Saylor] 24.6, “The Molecules of Life.” | Survey of proteins, carbohydrates, lipids, and nucleic acids |
| [PB-EOC] 17-1 through 17-4 in Chapter 17, “Amino Acids, Peptides, and Proteins.” | Overview and configurations of the 20 common amino acids; acid-base properties; isoelectric point pI |
| [RH] 3, “Amino Acids and the Primary Structures of Proteins.” | General structure of amino acids; details on each of the 20 common amino acids; other amino acids and derivatives; ionization of amino acids; creating proteins with peptide bond links |
Biochemistry is an integrative topic that connects many prior topics, and governed by the same laws that apply to inanimate matter. Biology – especially at the molecular level - is solid state chemistry. “Mother Nature is a polymer engineer gone wild!”
This lecture starts with amino acids as the building blocks of proteins, and in particular looks at their structure.
Prof. Sadoway surveys some amino acid properties, focusing on behavior in water. In an aqueous solution, the amino acid transfers a proton, becoming a zwitterion. Applying the Le Châtelier principle to scenarios of increased and decreased pH, Prof. Sadoway walks through the amino acid chemical responses, concluding: “This is what animates the stuff of life!”
Chirality can have profound implications for the biological response to particular chemicals. The drug thalidomide contained an enantiomer that had unforseen interactions with a human enzyme, leading to a wave of birth defects.
The lecture ends with discussion of the kinetics of organic compounds, specifically the extreme case of explosives. Prof. Sadoway describes the tremendous damage caused by the 1917 Halifax explosion, in which a ship loaded with TNT and other explosive chemicals caught fire in the harbor, causing the largest explosion of the pre-nuclear age.
| [saylor] Sections | Conceptual | Numerical |
|---|---|---|
| [Saylor] 12.8, “Polymeric Solids.” | 1 | none |
Michael Jackson. “Man in the Mirror.” Bad. Epic Records, 1987.
| Content | Provider | Level | Notes |
|---|---|---|---|
| 7.01SC Fundamentals of Biology | MIT OpenCourseWare | Undergraduate (first-year) | See Unit 1: Biochemistry |
| Modules | Organic Materials |
| Concepts | primary, secondary, and tertiary protein structures; protein synthesis |
| Keywords | zwitterion, protonation, deprotonation, titratable, electrophoresis, isoelectric point (pI), isoelectric focusing (IEF), protein synthesis, macromolecule, condensation reaction, peptide bond, disulfide bond, kilopeptide, primary structure, protein sequence, secondary structure, tertiary structure, alpha helix, beta pleated sheet, residue, substituent, conformation, hydrophobic, hydrophilic |
| Chemical Substances | nylon, polyamides, insulin |
| Applications | DNA analysis with electrophoresis gel, laundry detergent |
Before starting this session, you should be familiar with:
This session is the second of three sessions on biochemistry, and completes the foundation for the next session’s culminating exploration of the structure of DNA.
After completing this session, you should be able to:
| Book Chapters | Topics |
|---|---|
| [PB-EOC] 17-6 through 17-12 in Chapter 17, “Amino Acids, Peptides, and Proteins.” | Peptide and disulfide bonds; overview of protein structure; primary, secondary, tertiary, and quaternary structures; protein denaturation |
The lecture begins with further discussion about zwitterion behavior (introduced in Session 30), with the titration curve used to depict the relationship between degree of protonation and pH. An interesting application of zwitterion behavior is gel electrophoresis, in which an electrified gel column of varying pH allows a mix of different amino acids to be separated and analyzed.
Most of the lecture is devoted to protein structure. The peptide bond is the means of creating long macromolecule chains out of individual amino acids. These chains become a basis of life, as they encode information in different sequences of amino acids. (As an aside, amino acids can be remembered by their 3-letter “airport code” analogs.)
| Content | Provider | Level | Notes |
|---|---|---|---|
| 7.01SC Fundamentals of Biology | MIT OpenCourseWare | Undergraduate (first-year) | See Unit 1: Biochemistry |
| 7.343 Protein Folding, Misfolding and Human Disease | MIT OpenCourseWare | Undergraduate (elective) | Seminar on some biological implications of protein tertiary structure |
| Modules | Organic Materials |
| Concepts | denaturing proteins, lipids and their self assembly into bilayers, nucleic acids, DNA, and encoding information for protein synthesis, history of the discovery of DNA double helix structure |
| Keywords | denaturing, disulfide bond, triglyceride, zwitterion, aliphatic compound, cell wall, nucleotide, amphipathic, amine, base pairs, codon, Laue pattern, alpha helix, Oswald Avery, Erwin Chargaff, Rosalind Franklin, Francis Crick, James Watson, Maurice Wilkins, x-ray crystallography, biological replication |
| Chemical Substances | fats, oils, cholesterols, hormones, phospholipid, phosphatide, phosphatidylethanolamine, ribose, 2-deoxyribose, DNA, RNA, guanine, cytosine, adenine, thymine |
| Applications | cooking food, pickling food, hair styling, laundry detergent |
Before starting this session, you should be familiar with:
After completing this session, you should be able to:
| Book Chapters | Topics |
|---|---|
| [Saylor] 24.6, “The Molecules of Life.” | Overview of lipids and nucleic acids |
| [PB-EOC] 20-1 through 20-5 in Chapter 20, “Lipids.” | Fatty acids; waxes; fats and oils; soaps, detergents, and micelles; phospholipids |
| [PB-EOC] 21-2, 21-5, and 21-8 in Chapter 21, “Nucleosides, Nucleotides, and Nucleic Acids.” | Overview of nucleic acids; DNA and heredity; biosynthesis of proteins via translation |
After a quick review of the previous session, Prof. Sadoway begins with a discussion of denaturing proteins – disrupting protein secondary and tertiary structures. Examples of the denaturing process include:
Next, the lecture introduces lipids.
After lipids, the lecture proceeds with the structure of nucleic acids.
This lecture ends with a history of the discovery of DNA’s double helix structure: early insights by Oswald, Chargaff’s rule, Franklin’s x-ray crystallography experiment and its subsequent controversial use by Watson and Crick.
Watson, J. D., and F. H. C. Crick. “Molecular Structure of Nucleic Acids.” Nature 171 (1953): 737-738. (PDF)
Franklin, R., and R. G. Gosling. “Molecular Configuration in Sodium Thymonucleate.” Nature 171 (1953): 740-741. (PDF)
Judson, Horace Freeland. The Eighth Day of Creation: Makers of the Revolution in Biology. 25th anniversary edition. Woodbury, NY: Cold Spring Harbor Laboratory Press, 1996. ISBN: 9780879694784.
Maddox, Brenda. Rosalind Franklin: The Dark Lady of DNA. New York, NY: HarperCollins, 2002. ISBN: 9780060184070.
Watson, James D. The Double Helix: A Personal Account of the Discovery of the Structure of DNA. New York, NY: Touchstone/Simon & Schuster, 2001 (original publication 1968). ISBN: 9780743216302.
Francis Crick, James Watson, Maurice Wilkins — 1962 Nobel Prize in Physiology or Medicine
“It’s a Chemical Reaction, That’s All.” Music and lyrics by Cole Porter. From Silk Stockings. Fred Astaire, Cyd Charisse; directed by Rouben Mamoulian and Roy Mack. Original film release MGM, 1957. DVD, Warner Home Video, 2003.
Hank Ballard and the Midnighters. “The Twist.” (B-side with “Teardrops on Your Letter.”) Original release: King Records, 1959. Available on many reissue compilations, such as Their Very Best: Hank Ballard & The Midnighters. K-Tel, 2007.
| Content | Provider | Level | Notes |
|---|---|---|---|
| 7.01SC Fundamentals of Biology | MIT OpenCourseWare | Undergraduate (first-year) | See Unit 1: Biochemistry |
This self-assessment page completes the Organic Materials module, and covers material from the following sessions.
On this page are two weekly quizzes and solutions; relevant exam problems and solutions from the 2009 class; help session videos that review selected solutions to the exam problems; and supplemental exam problems and solutions for further study.
These short quizzes are given approximately once for every three lecture sessions. You should work through the quiz problems in preparation for the exam problems.
These exam problems are intended for you to demonstrate your personal mastery of the material, and should be done alone, closed-book, with just a calculator, the two permitted reference tables (periodic table, physical constants), and one 8 1/2" x 11" aid sheet of your own creation.
After you’ve taken the exam, watch the help session videos below for insights into how to approach some of the exam problems.
In these videos, 3.091 teaching assistants review some of the exam problems, demonstrating their approach to solutions, and noting some common mistakes made by students.
Clip 2: Final Exam, Problem 13
These additional exam problems from prior years’ classes are offered for further study.
