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Chemical Education: Software Abstract of Special Issue Number 6 Demonstrations in Organic Chemistry Garv - - ,Trammel1 Sangamon State Un vers t y Spr ngfle0. L 62794-92493
" D e m o n s t r a t i o n s i n O r g a n i c C h e m i s t r y " is a video laserdisc d e s i ~ m e dto p r o n d c vlsual examples of t h e chemistry of carbon compounds. These demonstrations a r c intended to mcrease students'intercst and learning by huvi n g t h e m see chemical phenomena and t h e n analyze t h e m at t h e molecular level. T h e content of this videodisc is designed for use at both the h i e h school a n d college level i n ~ e n e r a al n d o ~ a n i c chemi&y courses. Many demonstrations include praEtical examples of t h e chemistry of fuels, food, arugs, dyes, a n d polymers. Techniques such as t h e u s e of t h e separatory funnel i n extraction of an acid a n d thin layer chromatography of a dye mixture a r e shown. I n addition to chemical demonstrations, some segments show t h e u s e a n d manipulation of models of organic molecules including conformations of alkanes a n d cycloalkanes, enantiomers, a n d assignment of R- a n d S- configuration of chiral centers. Equations for m a n y of t h e reactions c a n b e shown a t t h e discretion of t h e teacher. Notes for teachers t h a t provide a brief explanation of t h e reactions a n d appropriate equations a r e included. The videodisc is arranged b y functional groups into ninet e e n chapters each w i t h several segments. Chapter a n d segment titles are:
C h a p t e r 7. Acetylene-Preparation a n d Reactions: Preparation and Combustion of Acetylene; Spontaneous Combustion of Acetylene in Chlorine; Molecular Model of Acetylene. .Chapter 8. Aromatic Compounds: Molecular Model of Benzene; Brumination of Cyclohcunnc, Cyelohexene, and Hcn7cnc; Hcnetmn of Brnmme w t h Benzene. Phenol, and Toluene: Electron Density of.4romntir llinas-Effrrt of Electron ~ o n a t i n eand ~ l e c t r o nwithdrawhe-~rouns: . . Electron Dms~ryof Benzene Rmas: Effect oiMethyl Croups; Chlorlnatmn uf Methyl Hcnrcrws; Hrnrrnr hlodrl. Chapter 9. Chirality: Chiral and Achiral Objects; R&SConfigurations; Glyceraldehyde and the Fischer Projection; Polarized Light and Organic Molecules.
Side B .Chapter 10. Nucleophilic Substitution Reactions: Solvalysis of i-Propyl versus tSutyl Bromide-Relative Rate of a Y versus Y Halide; Solvolysis of t-Butyl Chloride and tButyl Bromide-Effed of the Leaving Group; Reaction of Sodium Iodide with Bramobutane Isomers; Solvolysis of Bromobutane Isomers; Reaction of Silver Nitrate with Bromobutane Isomers; Salvalysis of t-Butyl Bromide-Effect of Solvent Polarity. Chapter 11.Alcohols: Oxidation of Alcohols with Chromic Acid; Oxidation of Gyleerine with Solid Potassium Permanganate; Lucas Test far Primary, Secondary, and Tertiary Alcohols; Reaction of Sodium with a Homologous Series of Alcohols. C h a p t e r 12. Aldehydes a n d Ketones: Patriotic colon; Addition of Bisulfite to Cyclohexanone; 2,4-Dinitrophenylhydrazine Test for Carbanyl Compounds; Icdoform Test for .Methyl Ketones; Silver Mirror-Tollens Test far Aldehydes; Oxidation of Ascorbic Acid; Aldol Condensation Reactions.
C h a p t e r 1. Methane: Combustion of Methane Balloons; Combustion of Methane in a Bunsen Burner; Methane Molecular Models.
C h a p t e r 13. Phenols a n d Quinones: Decalorization of Crystal Violet; Nitration of Acetaminophen; Ferric Chloride Test for Phenols; Extraction of Dicholorindophenol; Oxidation of Phenols with Sodium Periodate; Crown Ether Catalyzed Oxidatian of 2,5-Di-t-butyl-p-cresol; Nucleophilic Addition to Quinones; Chameleon Emulsion.
' C h a p t e r 2. C o n f o r m a t i o n o f A l k a n e s . a n d Cycloalkanes: Ethane; Butane; Cyclapropane; Cyclobutane; Cyclopentane; Cyclohexane.
Chapter 14. Aniline a n d Its Derivatives: pH of Aqueous Ammonia, Cyclohexylamine, and Aniline; Iodination of Aniline.
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Chanter 3. Relationshin of S t r u c t u r e t o Boiling ..Point ofAlkanes: B o h g Pvmt of a Homologous S e n w .\ludcls of Stmght Chain Alkanes; Bmlmp Points of Hrxnnr I ~ m w r s ; Modrlu of Hexane lsvmcrs.
Chanter 15. Carboxvlic Acids andDerivatives: Conductlnty ufCarboxylir Arid Solt~tiona;pll ofAcerlc Acid Derivatives; Ilydmphobrr Effect: Acetlr r\crd Sodium Acctatc Buffer.
C h a p t e r 4. Bromination of Alkanes: Light Inititiated Bromination of Pentane; Bromination of Hexane Isomers; Bromination of Alkyl Benzenes.
Chapter 16. Carbohydrates: Dehydration of Sucrose with Sulfuric Acid; Benedict's Test for Reducing Sugars; Blue Bottle; Oxidation of Sucrose with Potassium Chlorate; Osazane Formation.
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'Chapter 5. Oxidation of Alkanes, Alkenes, a n d Akohols: Permanganate Oxidation of Cyclohexane, Cyclahexm e , and Cyclahexanol; Reaction of Permanganate with Cyclohexane and Cyclohexene; Chromic Acid Oidation of Cyclohexane, Cyclohexene, and Cyclohexanol; Models of Alkenes. Chanter 8. Addition Reactions of Alkenes: Diels-Alder ~eac&onut'Tctmcynnwthylene and Anthmcmc; Chrmilunt~ncjcener:Addition of Oxygen to Tctrakis S,N-dimethylamino,cthylcnr; Addition of hdme to u-pinenr.
Chapter 17. Proteins: Effect of pH on the Solubility of Casein. 'Chapter 18. Dyes: Thiu I.aycr Chrnmatngmphy of Dyes; Mul~itnbric1)ycs; Effret ofplI on Tartrarme Dyeing; Dyeing with Indigo. Chanter 19. Polvmers: Formaldehvde Cooolvmen: Water ~bs&bent~ o l ~ m &Synthesis ; of ~ y l o n(6,6f-~ylonRope; High and Low Density Polyethylme; Combustion of Polyeth-
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ylene and Polystyrene; Synthesis and Properties of Pulystyrene; Thermoplnrtic Pulymcrs; Deilvtein Teat fnr Polyvinylchloride;Preparation of Methyl Metharrylate. The videodisc medium obviates concerns that normally accomoanv demonstrations: safety, availahility and diiposal of reagent& aost and time of constructing apparatds, and visibility of the presentations.
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chiral molecules are shown clearly, as are laboratory techniques. Teachers of introductory courses will also find this disc very useful, because it shows many demonstrations commonly done a t that level that involve hazardous materials or uncommon apparatus or substances. Examples are combustion of methaneloxveen mixtures. conformations of alkanes, relationship between structure (intermolecular forces) ~ - ~,and boiline ooints. chromic acid oxidations. chemiluminescence, silver mirror-Tollens Test, reactions and pH of organic acids and bases, effect of pH on proteins, dyes and dyeing, and polymers. ~~
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About This lssue John W. Moore and Jon L. Holmes University of Wismnsin-Madison Madison, WI 53706
Organic demonstrations have been used less frequently than those involving inorganic chemistry because of safety hazards, expense and availability of reagents, and visibility of the reactions. The videodisc overcomes these problems and also allows slow reactions to be compressed to a few minutes of video. Users of this videodisc will find that by providing a single viewpoint that applies to everyone in the audience it makes clear a number of points that are difficult to get across in a tvoical lecture. For example, the relationship between molecular structure and a projection formula is nicely shown by using a light source to project a shadow of a molecular model onto paper and then drawing a projection formula on the uaper . - with the model still present. In addition. the disc contains a l a x e number of organic reactions presented in an interesting, visual manner. Photochemistry and the rotation of plane-polarized hght hy
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HaldwarelSoftware Required "Demonstrations in Organic Chemistry" is a 12-in., double-sided, 60-minute, CAV-type video laserdisc in NTSC format (it is incompatible with the PAL standard used in many European countries). It may be operated from any videodisc player using a hand-held remote-control keypad or a barcode reader. To make the video presentation visible to students in a classroom either a large-screen color monitor or a color video ~roiectionunit will be needed. The size of the monitor (or'& need for a projectionunit) depends on the size of the class to which the presentation will be made. To Order This lssue Journal of Chemical Education: Software (often called JCE: Software) is a publication of the Journal of Chemical Education. There is an Order Form card inserted in this issue. If this card is not available. contact: JCE: SoRware, Department of Chemistry, university of ~ i s c o n s i n l ~ a d i son, 1101 University Avenue, Madison, WI 53706-1396; 608/262-5153 (voice);6081262-0381 (FAX).
