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1 RGANIC CHEM SMELL LAB (80/1200) name: bjective: to familiarize ourselves with organic functional groups and to learn how to recognize them in organic chemical diagrams. 1. You need to Draw a short, but not endless list of molecules, 8 per page, neatly. Put in the H atoms only in functional groups (such as aldehydes) and in all meth sized molecules. 2. Draw neatly, big, but only put 8 molecules per page or else I will go bonkers grading them. 3. Then you will examine many pleasant smelling molecules and circle their functional groups, naming these functional groups, and answering a few odd questions about some of these larger molecules. Some molecules contain 1, or 2, or even 3 functional groups. Do not circle any atoms NT IN FUNCTINAL GRUP column in table R. 4. Next, you will draw a MDIFIED VERSIN of TABLE Q. Draw the molecules on the lab, not the ones in table Q. Your table should help you discern the differences between the 3 series of chained hydrocarbons, just like Table Q does for you now. 5. Finally, the last pages show several organic reactions, please label which each of the reactions is. If you have met the 1200 minute lab minute requirement, surprise for you. You have to do all of this, but no conclusion and no cover. If you do not have enough lab minutes, you can add a cover and an extended conclusion describing hydrocarbons, and then all the functional groups. You will also describe each type of organic chemical reaction, with examples. This grade will run in the CLASSWRK part of the grade book but will be a lab report if you need the minutes. This is due ASAP.

2 Large rganic Molecules are so big, and so repetitive, that short cuts have been created to show them. In medicines and common things like caffeine, what at first glance appear to be complex molecules to non-chemists, are easily recognizable to us. With shapes, like hexagons, each corner is a carbon atom. If nothing is bonded to the corner, since each carbon has to make 4 bonds, sufficient hydrogen atoms are present even though they aren t drawn. Any other atoms besides H or C must be drawn for you to see. Double bonds and even triple bonds are apparent. Look at the examples, then determine the generic chemical formulas. By rule we will list the atoms of the chemical formula in this order: C, H, N,, etc. 1. This is cyclohexane, six carbons single bonded in a ring shape. The hexagon next to it is the shortcut diagram. Each corner is a carbon, and since each carbon must make 4 bonds, the formula is C 6 H This is called benzene. It s similar to the top molecule, but it has alternating double bonds. It can be simplified as the hexagon with three triple bonds. The formula here is C 6 H Number 3 is caffeine (AKA theophylline). The nitrogen atoms are labeled, but the other corners are all carbon. The molecule also has three dashes that lead to nothing. At the end of each dash is a really a carbon atom, each bonded to 3 atoms of H. What is the formula for this molecule? Answers at bottom of the page Fourth is theobromine (not bromine!), which is what makes chocolate taste so good. It s similar to caffeine, but not quite. What is that formula? 5. Aspirin (acetylsalicylic acid) for headaches is the fifth molecule. What is the formula? 6. Naphthalene is the stuff in moth balls that smells so bad! Your nose can detect it at levels of just 0.08 PPM! What s the formula? 3 7. The large multi-ringed molecule at the bottom is a type of cholesterol that clogs your arteries when you re old (eat well now!) Caffeine is C 8 H 10 N Chocolate is C 7 H 8 N Aspirin is C 9 H Naphthalene moth balls is C 10 H 8 7 Cholesterol is C 27 H 46

3 Draw these compounds page Draw 8 per page, spread them out, make them big, you do NT have to draw all of the hydrogen. Use pencil, no big cross outs will be accepted! page 1 propane ethanol pentane methanoic acid 3-nonene di-propyl ether 2-butyne 1,1,1 trifluoro ethane page 2 1-bromo-2-hexyne octane 4-nonyne butyl methanoate butane 2,3,6, tri-chloro decane propene ethyl propyl ether page 3 1-butanol methyl-propyl ether pentanal propanoic acid tri-iodo methane 3-hexanone 2,4 dimethyl hexane ethanamide page 4 ethanoic acid 1 bromo,4 chloro 2-pentene chloromethane butyl hexyl ether ethyl butanoate heptanoic acid 3 pentanol 1-bromo, 3-chloro, 4-fluro, 6-iodio nonane page 5 ethanal 3-heptanone hexanamide methyl-ethyl ether ethene propyl hexanoate 3,4 dibromo1 hexyne cyclo-pentane page 6 4 ethyl,2-methyl octane ethyl ethanoate 2-octene 2-octyne 3-hexanamine pentanamide methyl pentanoate cyclo-butane

4 SCENT STRUCTURAL FRMULA Types of Functional Groups present banana CH 3 --C-C 5 H 11 Name this compound caraway (rye bread) CH 3 C CH 3 CH 2 How many hydrogen atoms in molecule? cinnamon coconut H geraniums (flowers) How many carbon atoms in molecule?

5 SCENT STRUCTURAL FRMULA Types of Functional Groups present hyacinth (flowers) H jasmine CH 2 C CH 3 H licorice H C C C CH 3 H H H mushroom H CH 2 CH CH (CH 2 ) 4 CH 3 Total hydrogen atoms? orange C 8 H 17 C CH 3 Name this compound peach (CH 2 ) 6 CH 3 Total hydrogen atoms?

6 SCENT STRUCTURAL FRMULA Types of Functional Groups present pear peppermint roses CH 3 Total hydrogen atoms? spearmint C C CH 2 violets Total number of carbon atoms?

7 Types of Functional Groups present vinegar Name this compound strawberry HC H vanilla C 2 H 5 wintergreen How many total double bonds in molecule?

8 Homologous Series Name general formula n = number of carbon atoms Name (4 Carbon chains) EXAMPLES Structural Formulas (draw all hydrogen atoms) alkanes butane alkenes 1-butene alkynes 2-butyne Example of a Diagram Condensed Structural Formulas Branched alkane at least 6 carbons long Branched alkene at least 6 carbons long Branched alkyne at least 6 carbons long

9 In each BX of the following organic reactions, name each type of reaction shown. CH 4 + Cl 2 CH 3 Cl + HCl enzymes C 6 H 12 6(AQ) C 2(G) + C 2 H 5 H (AQ) + water Name the type of reaction, and BALANCE THIS

10 Draw the structural diagrams AND condensed structural formulas showing these 3 reactions. Substitute in NE halogen atom at a time. Substitute in a fluorine atom with ethane, forming fluoro-ethane + HF Substitute in a chlorine atom with propane, forming 1-chloropropane + HCl Substitute in an iodine atom with propane, this time forming 2-iodo-propane + HI Write the balanced chemical equation for the fermentation of glucose. Structural model of GLUCSE C 6 H 12 6 Draw the structural diagrams of the proper number of the product molecules that form during this reaction. Water with yeast cells

11 Addition reactions require you to start with an unsaturated hydrocarbon, so you have the room in the molecule to add either F 2, Cl 2, Br 2, I 2, or even H 2. You must start with an alkene, or alkyne. Alkenes open the double bond to a single, allowing two places to open to add the diatomic halogen (or hydrogen). If you start with an alkyne, you convert the triple bond to a double, then add in the two new atoms. In each box, draw structural formulas + write the balanced chemical equations for: Add a bromine molecule to 2-pentene Add a chlorine molecule to 2-butyne Add a hydrogen molecule to propene Saponification is the production of soap. Reorganize the first 4 letters of this reaction name to remember this one. LABEL the triple ester (FAT), the 3 bases, the triple alcohol (in this case glycerol) and the 3 SAP molecules. CH 2 H CH 2 C (CH 2 ) 14 CH 3 CH C (CH 2 ) 14 CH 3 + 3NaH CH H + 3CH 3 (CH 2 ) 14 C 2 Na +1 CH 2 H CH 2 C (CH 2 ) 14 CH 3

12 Esterification is the process of combining organic acids to alcohols by the removal of HH (L), forming an ester. Strangely, acids are known for liberating hydrogen ions when ionizing in water. Alcohols do not ionize at all. In this reaction, the acid will lose the H part of the CH group, and the alcohol will lose just the H from its H group. The HH forms water, and the molecules join with a C group in the middle. We always name esters this way: FIRST name is the group attached to the oxygen tail, the second name contains all the other carbons. Draw and label the structural diagrams for propanoic acid and for ethanol, and the two products. Make sure the functional groups are both drawn towards each other. Circle the H and the H that makes the water. NAME the ester that forms. Now combine methanol with hexanoic acid to produce the wonderful smell of bananas! Do the same as above, draw 2 diagrams for the acid and the alcohol, circle the H and the H that forms water, then draw and properly name the new ester.

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