EXPERIMENT 24 Se PROPERTIES OF SATURATED HYDROCARBONS GOALS 1, To understand the structure of alkanes 2. To investigate shapes of saturated hydrocarbons 3. To explore the reactions of saturated hydrocarbons INTRODUCTION ‘The simplest organic compounds to understand are alkanes. They are hydrocarbons and contain only carbon-carbon and carbon-hydrogen single bonds. They are relatively inert, undergoing few reactions ‘under normal conditions, but are of particular importance because understarding them isthe basis for understanding more complex molecules that are of prime importance in biological systems. ‘Alkanes are also the simplest organic substances to name. The naming ofall organic molecules is governed by strict rules, and the root words for many names are derived from the names of the first 10 to 20 alkanes in the cries. In order to progress in your study of organic and biological chemistry, {you will ned to be familia with the conventions for naming compounds. You should refer to your textbook for an overview of the rules. ‘Alkanes can only undergo a few chemical reactions without using some kind of forcing conditions. The most important of these is combustion, the combination with oxygen to generate carbon dioxide, water, and energy in the form of heat and light, We use this reaction to cook om a gas stove, heat homes with oil or gas heat, and run internal combustion engines to drive ears. Under some conditions, alkanes can be converted into haloalkanes, which have somewhat diferent properties, ‘among them a lick of flammability. They are often studied together in courses like this, because both classes contain only single carbon-carbon bonds This exercise will examine physical properties of alkanes and haoalkanes using hexane and dichloromethane, CH,Ch, a representative examples. Consider what you see, and! interpret your “observations inthe ight of what you know about polarity and density. For the second part of the experiment, you will be using molecular models. Depending on the tools availabe in your lab, these may be physical ball-and-stick models or computer-generated 3- dimensional pictures. Molecular modeling exercises should give you a feel for the way in which the shape ofa molecule is govemed by the types of bonds present and by the sire of the molecule. A Static picture on « piece of paper cannot show the twisting and tumbling of long chains of earbon ‘toms inthe same way a physical or compuler-zenerated model ean.234 Expenment 24 REFERENCES Stoker, H. S. General, Orsunic, and Biological Chemistry; Cengage Learning; Chapter 12. Review topics ‘© Structural formulas © Isomers © Conformations © Covalent bondi WEB RESOURCES ‘These fesources are best viewed using the Accelrys Chime 2,6 Chime plugin from hap Waccetrys.com(products/informatics/cheminformatics/chime/no fee php Life's Molecules. hutp://biology.wse.ma.edu/biology/courses/molecules/ Cyclic Alkanes and Alkenes. hitp://rwvw.elmburst.edu/~chm/vchembooX/S06cyelic. html SAFETY NOTES Organic chemicals often have strong odors and are usually volatile and flammable. Treat them with respect, and avoid inhaling the vapors, using them in the hood whenever possible. Use small amounts of materials, and discard them into appropriately labeled waste jugs when finished, not down the sink. ‘Some chemicals in this experiment may be strongly acidic—treat all the chemicals used with respect. You may wish to wear gloves during this experiment, and you must wear chemical splash goggles.Propeties of Saturated Hycrocarons, 235 EXPERIMENTAL PROCEDURE PART A. PROPERTIES OF SATURATED HYDROCARBONS Step I. fn each of two test tubes place 1 mi of water. Add to the firsttube drops of hexane and tothe second § crops of dichloromethane, mix each well, and record what you sec. ‘Step 2. In two other test tubes place I mil. (about 20 drops) of toluene (another hydrocarbon). Into ‘one samipe mix 5 drops of dichloromethane, and into the oder supe mix 3 drops of hexane, Mix ‘ach well, and record what you see. ‘Step 2. Place 10 drops of hexane in a well ofa spot plate, and 10 drops of dichloromethane in & ‘second well Test each with the conductivity tester to determine if hey will conduct electricity ‘Step 4, Place | mL. of hexane in an evaporating dish inthe hovd, and touch a lighted match toi Recond what you see. Repeat his exercise wih I mL of dichloromethane, Step Place 10 drops of hexane in teat tube dd | deop of iodine solution and observe ‘Step 6, Repeat Step 5, bu this time use dichioromethate as the reactant. PART B. STRUCTURES OF ALKANES ‘Using molecalar models or computer-based molecular modeling program, make models ofthe following compounds. Draw exch model, and answer the questions relatieg ti hexane civ 2dimethyleylopentane 23-dimetyfbuane tran 2-dimsthyleyelopentane — 5 rmethyeyelopencane “emetyipentane methylene PART C. EXERCISES [Ansvte the questions en the report form concerning the properties of alkanes an halodkanes.EXPERIMENT 24 REPORT: PROPERTIES OF SATURATED HYDROCARBONS Name Partner Date. PART A. PROPERTIES OF SATURATED HYDROCARBONS Observations on the Physical Propertis of Hexane and Dichloromethane Hexane Dichloromethane Mixed with water Mixed with toluene ‘Tested for conductivity |. Why do alkanes and haloalkanes dissolve in toluene but fail to dissolve in water? 2, Do alkanes and haloalkanes conduct electricity? Why oF why not? 3. How do the densities of alkanes and haloalkanes compare? Reactions of Hexane and Dichloromethane Hest | __Detloronetinne With oxygen (combustion) | __| With potassium dichromate | FF Withiodine 7 4. Considering hexane and dichloromethane as models, state 4 conclusion about the reactivity of alkanes and haloal¥anes.PART B. STRUCTURES OF ALKANES Drawings hexane ‘eis-1-2dimethyleyelopeniane 2Finethy butane ‘rans-I2edimethyleyeiopentane F-chiorohexane ‘rans S-eyelopeniane Tmetiyeyclopentane eyelohexane Smethy pentane Taetiylpentane 1. Whieh of the above compounds ate isomers of each other? 2. Explain why cis-1,2-dimethyleyclopentane is considered a different substance from trans-1 2 dimethyleyclopentane,Properties of Saturated Hydrocarbons. 241 PART C. EXERCISES |. Write structures forthe Following named alkanes and haloaikancs. For esch compound, use both the condensed siructural formula and the line-angle structure. methyleyeloprepane cis-1,4-dimethyleyclohexane srans-1,3-dietbyleyelopentane 2. Give correct names for each of the following compounds. rae ee 3. Draw structures for the major products for each of these reactions. Ifno reaction oceurs, write N.R, Cr +o COY* xcxosts0, $=EXPERIMENT 24 PRELAB EXERCISES PROPERTIES OF SATURATED HYDROCARBONS Name Partner ___ 1. What isa saturated hydrocarbon? Give two examples, showing both the names and the srucures. 2. What physical properties do you expect 1 se in saturated hydrocarbons? 3. What are the products of combustion in saturated hydrocarbons? 4. Draw structural fonnulas for wo isomers of hexane, Cally, 5. Using reference sources, find the relative densities of eMorofonm and methane, Density of eloroform, Density of pentane How could you makes layered mixture of pentins sre miscible? ehloreform, and water if chloroform and pentane