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Hydrocarbon isomers

Hydrocarbon isomers. by Nathan Hickey & André Gagnier. Less interesting, (but crucial) stuff first. Curricular expectations (SCH 4U): B. Organic Chemistry

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Hydrocarbon isomers

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  1. Hydrocarbon isomers by Nathan Hickey & André Gagnier

  2. Less interesting,(but crucial) stuff first... Curricular expectations (SCH 4U): B. Organic Chemistry B3 demonstrate an understanding of the structure, properties, and chemical behaviour of compounds within each class of organic compounds. B2.3 build molecular models for a variety of simple organic compounds. B3.5 explain the concept of isomerism in organic compounds, and how variations in the properties of isomers relate to their structural and molecular formulae. … now the more interestingstuff.

  3. Challenge! (the hook, targeting the students’ competitive natures) You have 2 minutes: In groups of two, Use a molecular kit and build C6H14 in as many different ways as you can. Then draw your results. GO!

  4. Follow-up question:Are these the same? What is their chemical formula?

  5. C3OH8          and       C3OH8 They both have the same chemical formula! So again, are they the same?

  6. How about these? They're all C5H12. So are they all the same?  All different? In groups of 2,use a molecular kit to discover.

  7. Day 1: Introduction to constitutional isomers • Begin with the Isomer Challenge on slide #3 followed by the questions on the next three slides. (Inquiry-based learning) • Between every new question will be in-class discussions where the students must propose hypotheses and take a stand. • Following this is an introduction to the term "isomer“ and the theory of constitutional isomers. • End the period with the on-line Isomer Construction Set, with a few questions assigned as homework.

  8. Day 2: Lab To demonstrate that isomers have different physical and chemical properties, the students will evaluate the boiling point and density of the following compounds: • Propanol • Isopropanol After the labs, the rest of the period will be spent discussing why it is that isomers react differently (different electron density, different polarity, etc.).

  9. Day 3: Alkene isomers (stereoisomers) Using molecular kits, explore the nature of stereoisomers. Practice exercises are posted on the class Wiki. Students are also asked to determine whether alkynes also have stereoisomers.

  10. Potential Student Difficulties

  11. Safety Concerns • the Bunsen burners used to determine the compounds' boiling points (obvious fire and burn hazards). Proper care must be taken and safety goggles must always be worn. • the organic compounds that we handle will have to be dealt with carefully.  Some of them are toxic and all of them are flammable!  Proper disposal must be ensured afterwards.

  12. Evaluations

  13. Practical Applications and Societal Implications • Cis- and trans- fatty acids in foods • trans-fatty acids are generally associated with health risks including coronary heart disease • The mechanisms through which these compounds contribute to these health risks are under investigation • Octane rating of gasoline • Simply, this rating can be used as a rough measure of the isomeric content in the fuel • Chiral drug industry • Exploiting isomers in pharmaceuticals to gain better efficacy. • Not to be discussed in depth as it includes classes of isomers outside the scope of the class

  14. References: • http://www.flatworldknowledge.com/pub/basics-general-organic-and-bio/421680#web-421674 • (This site has general information on organic chemistry and is very simple and straightforward) • http://chemed.chem.purdue.edu/genchem/topicreview/bp/1organic/organic.html • (A more advanced site with information on organic chemistry) • http://antoine.frostburg.edu/cgi-bin/senese/tutorials/isomer/index.cgi • (A web-based isomer tutorial. This site contains the virtual isomer construction set) • www.a-levelchemistry.co.uk/ • (The isomerism exercises were obtained from this site)

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