safety goggles 1 ball- and~stick molecular model ldt/4 students
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1 Text reference: Section 24.1 The physical, chemical, and biological properties of molecules are determined, to a large extent, by their three-dimensional shapes. Molecular substances made up of molecules that pack tightly together often form large, beautiful crystals. Other substances made up of molecules that do not pack together remain liquids even at low temperatures. Many medicinal drugs are effective because their shapes resemble those of molecules in the body. donsequently, an understanding of molecular shape is very important to an nnderstanding of chemistry or biology. Like many people, you may find it easier to work in three dimensions if you use molecular models. By working with models, you can learn to visualize aod understand molecular shapes. In this experiment, you will use ball-and-stick models to study the shapes of hydrocarbon molecules. Make models of hydrocarbon molecules. Compare the threeodimensional models with the structural formulas of chemical conlpounds. Make models of structural and geometric isomers. safety goggles 1 ball- and~stick molecular model ldt/4 students Note the Safety Symbol used here. Review safety information on pages Always wear safety goggles when working in the lab.
2 Refer to Table 49.1 for the color code of the atoms. As you construct each model, complete Table 49.2a and Table 49.2b, Table 49.! Color black yellow red blue green purple orange Color Code for Models Atom Represented carbon hydrogen oxygen nitrogen chlorine iodine bromine 1. Make a model of methane, CHv Are all the angles formed by any two C--H bonds the same? 2. Make a model of ethane, C2H 6. Can you hold one carbon and its hydrogens in a fixed positio n and rotate the other carbou and its hydrogens, without breaking the C--C bond? 3. Make a model of propane, Calls. Can this model be rearraoged to form a different molecule? 4. Make a model of butane, C4HI0. Can this model be rearrar~ged to form a new molecule that has the same but a different structural formula? If so, name the structures. Molecules that have the same, but different structural formulas, are called structural isomers. 5. Make a model of pentane, C5H~2. Construct as many structural isomers of pentane as you can. For each of these structt~ral isomers, give the name of the structural formula here and draw a sketch in Table 49.2a. 298 Experiment 49
3 6. Construct a model of hexane, CaHt4. Manipulate the structure to form a ring (you will have to remove two hydrogens to join the ring). This ring structure is cyclohexane. Manipulate your cyclohexane molecule so that two carbons directly across the ring from each other are above the plane of the other four carbons. This is called the boat conformation. Now manipulate the molecule so that one of these carbons is above, and the other below, the plane of the remaining four carbons. This is the chair conformatiot~. In Table 49.2a, draw these two conformations. Is there free rotation about the C--C bond in cyclohexane? 7. Make a model of ethene, C~H 4. Can you rotate the carbons about tbe double bond? 8. Remove one hydrogen from each carbon in ethene and replace it with a chlorine. The name of the resulting compound is 1,2-dicbloroethene, C~H~C12. There are t~vo structures possib!e for this cmupmmd. They are called geometric isomers, and are disfinguisbed by the prefix cis or the pre~l tratzs added to the name. Construct models of both geometric isomers. 9. Make a model of botene, C4Hs. This compound has two structnra[ isomers. Name these isomers and, in Table 49.2b, give their molecular and structural formulas. Are there also geometric ("cis" and "trans"). isomers for butene? 10. Make a model of ethyne, C2H2. In the space provided in Table 49.2b, describe the shape of the molecule. Can you rotate the molecule about the triple bond? 11. Make a model of benzene, C6H6, using alternating single and double bonds to approximate the aromatic bonds. Do all the atoms in this molecule lie in the same plane? Can benzene exist in the boat aud chair conformations? Hydrocarbons: A Structural Study 299
4 Name Class Date Table 49.2a In formation on Molecular Models Methane Stroctural Formula Ethmm Structural Fornmla molecular fornmla H--C--H angle? Rotation around C C bolnd? Propane Structura! Formula Other isomers? Pentaue Structural Formulas molecular forlllola Cyclohexane Structural Fommla molecular fornlola Conformations Boat Chair Rotation arom ~ C Cbond? Hydrocarbons: A Structural Study 301
5 Table 49.2b Information on Molecular Models ~}~ ~ ~(o 1,2-Dichloroetheoe Structural Formula Structural Formula Sketcii cis- Rotation around C:C bond? molecnlar formula _ Ethyne molecolar formula Structt~ra[ Formu[as Structural isomers Structural FormuIa Shape? Rotation around C~,C bond? Benzene Structural Formula: is the molecnle planar? Geometric Isomers Chair and boat conforlnations? 302 Experirnent 49
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