1. Experiment 2 DISTILLATION AND GAS CHROMATOGRAPHY OF ALKANES

2. Objectives  To explore the relationship between molecular structure, intermolecular forces and boiling points of various types of compounds.  To learn techniques of simple distillation and gas chromatography (GC).  To use these techniques to separate and identify compounds in an unknown mixture.

3. Before coming to lab…  It is *highly recommended* that you watch the following video prior to coming to lab. http://www.youtube.com/watch?v=3JlI PnyrZMw http://www.youtube.com/watch?v=3JlI PnyrZMw

4. Structure, IMF, and Boiling Point  Alkanes are compounds which consist of ONLY carbon and hydrogen.  Straight chain alkanes will have a boiling point higher than that of a branched isomer due to greater surface area in contact, thus greater LDF between adjacent molecules.

5. Table 2.1 Unknown Molecular Formula bp ( o C) Structure Pentane (GC SOLVENT) Use www.chemexper.comwww.chemexper.com These can be drawn in Kekulé form OR skeletal! n-hexane 3-methylpentane n-heptane isooctane (2,2,4- trimethylpentane)

6. Distillation  Distillation is a laboratory technique used for separating and purifying liquids.  To separate two or more liquids by distillation, you first heat them in a flask.  The more volatile liquid (the liquid with the lower boiling point) will typically evaporate first and the vapor will pass into a condensing column, where it can revert into a liquid (condense) on the cool glass where it trickles into a collection flask.  Heating further will cause the less volatile liquids to evaporate and distill at higher temperatures.

7. Distillation  Involves vaporization, condensation, and collection of the condensate (distillate).  The temperature of the distillate is measured by a thermometer placed in the path of the vapor. Collect four 5 mL fractions in small test tubes!

8. Simple Distillation  Simple distillation is most effective when the mixture contains only one volatile component.  More than one….most effective if the boiling points of the components differ by at least 70 ºC.

9. Chromatography  Chromatography is the collective term for a family of laboratory techniques for the separation of mixtures.laboratory techniques separation of mixtures  It involves passing a mixture dissolved in a "mobile phase" through a stationary phase, which separates the analyte to be measured from other molecules in the mixture and allows it to be isolated.analyte

10. Gas Chromatography  In Gas chromatography, the MOBILE PHASE is helium gas.  For this reason, gas chromatography will be used only to separated volatile compounds in lab.

11. Gas Chromatography Lower boiling component Higher boiling component  Typically, a nonpolar packing material is used as the STATIONARY PHASE.  For this reason, when analyzing compounds of similar polarity, the compounds will elute in order of volatility.

12. The individual fractions collected are analyzed by GC during the course of the distillation. Based on peak size, it is evident that as the distillation proceeds, the later fractions contain mainly the higher boiling component of the mixture. Original Sample Fraction 2 Fraction 5 pentane hexane Unknown X Original Sample Mixture Fraction 1 Fraction 5 Pentane ( GC Sample Solvent) Alkane #1 Alkane #2 The individual fractions collected are analyzed by GC during the course of the distillation. Based on peak size, it is evident that as the distillation proceeds, the later fractions contains only the higher boiling component of the mixture.

13. Product Analysis (Quantification of Components…Adjusted Area Percent)  Most often you will dissolve your compound or mixture in a low boiling solvent for GC analysis.  The relative areas of the components of interest must therefore be adjusted, to exclude the large % area of the solvent peak.  Refer to page 21 for further explanation. Adjusted area % = area % of peak of interest X 100 sum of area % of ALL peaks of interest* *omit area % of solvent peak

14. Experimental Procedure (Simple Distillation)  Add the unknown mixture and 3 boiling chips to a round bottom flask.  Set up a simple distillation apparatus.  Begin water flow through condenser and apply heat to the flask.  Collect liquid distillate in small test tubes as it leaves the condenser.  Keep track of the temperature range for each fraction as it is collected.  Collect (4) 5mL fractions, leaving the final 5mL in the boiling flask.  Prepare GC sample for analysis.

15. Product Analysis (GC Analysis) Analyze your FIRST and FOURTH fractions by GC. SAMPLE PREP: Transfer 5 drops of your sample into an auto sampler vial using a plastic pipet. Add 1 mL of GC solvent (pentane) from the solvent dispenser in balance room. Be sure to record your GC vial slot # in your laboratory notebook. You will receive an email to your UNCW account when GC results are ready for pick-up!

16. Table 2.3 You cannot complete this table until you obtain your GC results from the board outside of Dobo 203. The standard chromatogram will be provided on the front of the envelope containing the chromatograms. Use only the standard run for your lab section! Peak # Compound Identity Standard R t (min) Fraction #1Fraction #4 Sample R t (min) Area % Adjusted Area % Sample R t (min) Area % Adjusted Area % 1 2 3

17. SAFETY CONCERNS  All compounds used in today’s experiment are extremely flammable. Wear safety goggles at all times and use extreme caution!

18. WASTE MANAGEMENT  Pour all liquid waste into the bottle labeled “LIQUID ORGANIC WASTE”.  Do NOT pour any waste down the drain!

19. CLEANING  Disassemble distillation apparatus in your lab hood.  In your lab hood, rinse all glassware with wash acetone ONLY directly into a beaker from your drawer (DO NOT REMOVE DISTILLATION APPARATUS FROM YOUR HOOD AT ANY TIME.) Return distillation glassware to case in your hood. Return all other glassware to your lab drawer.

20. LABORATORY NOTEBOOK (Pre-lab) o OBJECTIVE (Must clearly state…) o What is the goal of the experiment? o What technique will you used to accomplish it? o How will you determine if it worked? o TABLE OF PHYSICAL DATA (Complete the following table using MSDS sheets from http://hazard.com/msds/ ONLY. Wikipedia is unacceptable)http://hazard.com/msds/ o REFERENCE TO PROCEDURE (Must include…) o full title o Edition o authors o page numbers where actual procedure can be found CompoundMW (g/mol)bp (C o )d (g/mL)HAZARDS Pentane n-hexane 3-methylpentane n-heptane isooctane

21. LABORATORY NOTEBOOK (In-lab) DATA/CALCULATIONS Record which unknown was used Record distillation range of each fraction collected Record GC vial slot number for fraction #1 Record GC vial slot number for fraction #4 Record GC sample solvent used Show one EXAMPLE of an adjusted area percent calculation EXPERIMENTAL PROCEDURE In paragraph form, briefly describe the procedure that you actually followed during the lab. Paragraph must be written in PAST TENSE, PASSIVE VOICE. Include any volumes of chemicals used during the experiment Include any mistakes, accidents, or observations if necessary.

22. For Next Lab…  Experiment 4 Pre-lab Notebook Entry due!  It is *highly recommended* that you watch the following link prior to coming to lab! (must cut/paste address) http://www.youtube.com/watch?v=yoYECMP_1iI&feature=related  This video is not exactly like the procedure we will use, however will provide a good example of the experiment!