Sizzling Organic Chemistry Dramas!

by Brenna Lorenz
    
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by Brenna Lorenz
    Offered here for your enjoyment are four short organic chemistry plays that illustrate reaction mechanisms. These were performed in an actual organic chemistry class. You are free to use them in your class. (If you do, let me know how it turns out). The students wore signs around their necks identifying their parts in the drama. Electrons were drawn on posterboard and exchanged where appropriate. Bonding was illustrated by having the participants hold onto the electrons being shared. When asking for parts, the students would say, "Just don't give me any girl parts (or boy parts)."  I would tell them that there weren't any girl parts or boy parts, just atom parts. Most of the students really enjoyed the dramas and competed for parts... but be warned! I had to discontinue the plays because a student complained to the Dean that the plays were sexually offensive, even though: (1) the students were repeatedly reminded that atoms and molecules don't have gender and (2) students never touched each other and (3) these plays aren't nearly as raunchy as Shakespeare!
 
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Electrophilic Addition

(A Molecular Drama)

Characters: Secondary carbon (Sec) is sharing four electrons with Primary Carbon (Prim) to form a propene molecule. Along comes a hungry electrophilic Hydrogen (Hyd) who is bonded to an electron-hogging Chlorine (Chlor).

 Hyd: Oh, look at all those electrons on that propene!
Chlor: What's with you? Aren't my electrons good enough for you?
Hyd: (disgusted) Your electrons. That's the whole trouble with you. They're our electrons, you pig!
Prim: Hi, Hydrogen! Nice nucleus!
Chlor: You keep your electrons away from my Hydrogen's nucleus!
Hyd: (to Propene) Would you share your electrons with little old me?
Prim and Sec: Yes!
Hyd: (Shoving electron pair at Chlorine) Here! Keep your precious electrons! I'm going to bond with someone who appreciates me.
(Hydrogen grabs one of the electron pairs shared by Secondary and Primary Carbons, and after a brief struggle, Secondary lets go, leaving Hydrogen bonded to Primary.)
Sec: Help! I'm a carbocation! Someone give me some electrons, quick! (Spots Chlorine.) Hey, you've got electrons to spare. Share them with me.
Chlor: You are very attractive, but my parents always warned me about organic molecules... (Chlorine looks worried, but doesn't try to run away.)
Sec. Don't give me that stuff! We'll smell great together. (Secondary grabs a pair of Chlorine's electrons and makes a bond.) Ah, that's better! (Sec turns angrily to Primary.) How come I always have to be the carbocation? What's wrong with you being a carbocation once in awhile?
Prim. (smugly) It's against the Rule, as you know perfectly well.
Hyd: What Rule?
Prim: Markovnikov's Rule. You see, Secondary there has all kinds of family support. There's me and the Primary on the other side. We lend Secondary as much spare charge as we can afford when Secondary gets stuck as a carbocation. But if I were to become a carbocation (shudder), Secondary there is the only one who could help me out and that's not much.
Hyd: I'd help you, bond-mate!
Prim: That's sweet of you, Hydrogen, but let's face it. You've barely got enough electrons to keep your own nucleus covered.
 
 

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Becoming an Alcohol

(A Sad Tale of a Good Oxygen Gone Bad)

Characters: A Primary Carbon (Prim) is sharing four electrons with a Tertiary Carbon (Tert) to form 2-methylpropene. A Hydrogen (Hyd) is bonded to an Oxygen (Ox); both are part of a water molecule. A Sulfuric Acid (Sulf) molecule is lurking nearby. Another Oxygen (Ox-2) (part of another water molecule) takes part in the last stages of the reaction.

 Hyd: (Sighs) I'm tired of being part of a water molecule. I'd like to be part of something bigger and better. (Seeing 2-methylpropene.) Like that molecule over there!
Tert: (to Prim) There's one of those water molecules. They never know whether they want to be the acid or the base.
Hyd: (shyly) Will you share electrons with me?
Prim: You're kind of cute, but...you know.
Tert: We can't let just anybody protonate our double bond. Nothing personal.
Hyd: Why? What's wrong with me?
Prim: Well, no offense, but...we just like to see a bit more nucleus, that's all! Someone a little more acidic than you are, dear.
Hyd: Oh! (Sighs again.)
Ox: Wow! (Staring at Sulfuric Acid) Would you get a load of those protons! Hubba, hubba! (Oxygen lunges at Sulfuric Acid.)
Hyd: Hey!
Ox: Gimme that proton! I want it!
Sulf: Sure, no problem. (Sulfuric Acid hands the Proton to Oxygen)
Ox: Look at me now! I've got three! I'm a hydronium ion. Wait 'til the other water molecules see this.
(Hydrogen undergoes a change when oxygen gets protonated. Hydrogen ceases to be a shy, retiring atom and becomes an aggressive, bond-eating electrophile.)
Hyd: Where's that 2-methylpropene? Let me at 'em!
(Hydrogen lunges for the organic molecule.)
Tert: Oh, man! Get a load of that nucleus! Proton city! Protonate me, baby!
Prim: No, me! Protonate me! It has to be me. (Angry aside to Tertiary:) You know that! I can't be a carbocation. (Primary whips a pair of electrons over to Hydrogen, who grabs them and simultaneously lets go of Oxygen.)
Ox: Hey! That's the trouble with hydrogens. They are so fickle.
Tert: Oh, no. I just hate being a carbocation! (To Oxygen): Hey! You in the water molecule! Don't go away! I need some of those electrons. (Tert grabs a pair of Oxygen's electrons.)
Ox: Hey! I don't like this. This is more than I want to deal with. I can't keep track of you and two hydrogens. My nucleus feels ... exposed. (Oxygen hugs the bonding electrons closer to its nucleus.)
Ox-2: Well, if you can't handle your hydrogens, I know someone who can. Me! (Ox-2 snatches one of Oxygen's hydrogens and runs off with it, cackling gleefully.)
Ox: Oh, no! Do you realize what we are now? We're an alcohol! I don't want to be part of an alcohol! My parents didn't raise me to be in an alcohol!
Tert: Well, then why did you bond with me?
Ox: I didn't realize what I was getting into until it was too late! And to think I was once part of an ozone molecule in the upper atmosphere. How can I have fallen to such depths, so fast? (Molecule drifts offstage with oxygen going on and on about his fate.) And now it's the gutter for me. Filthy organic molecules! If my mother could see me now, hybridizing my orbitals with a lowly carbon. How degenerate can you get...

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A Blind Date With the Bromine Twins

[When this play was performed in my class, one twin was played by a big American guy, and the other by a small lady from the Philippines.]
Characters: Two sp2-hybridized Carbon Atoms (Carb 1 and Carb 2) in a cyclopentene are hanging out in the solvent waiting for their blind date. Presently they see a bromine molecule approaching, made up of two Bromine Atoms (Brom 1 and Brom 2).

Carb 1: What's that molecule over there? Is that our date?
Carb 2: I don't know. I hope not. It looks like a halogen.
Carb 1: Yeah, it does look like a halogen. Ugh, it's a pair of fat bromines!
Carb 2: I know they're supposed to be great electrophiles, but I can't see what they have to offer us. I mean, look at that! They may have great nuclei, but they're buried under layers and layers of electrons.
Carb 1: Yeah, maybe they are electrophiles, but I am a nucleophile and I'm not seeing any nucleus!
Brom 1: (Catching sight of the cyclopentene) Oh, look, that must be our date.
Brom 2: Hmm. Not a bad electron density for a pair of carbons.
Brom 1: (Giggling) They're pi bonded. Kinky!
Brom 2: They don't look too happy to see us. What if they refuse to share those lovely electrons?
Brom 1: Don't worry. I know how to handle carbons. Here, you let me hold most of these electrons while I stand out of sight behind you and you pretend to be a cation.
Brom 2: A cation?!? Just what kind of halogen do you think I am?
Brom 1: Hey, it's just temporary! It will only be until you grab hold of some of those great electrons. And that's what we're in this for, isn't it? Electrons?
Brom 2: Yeah, I guess you're right. (Bromine 1 stands behind Bromine 2, while Bromine 2 reluctantly lets Bromine 1 carry most of the electrons.) Ugh, this feels nasty.
Carb 2: Hey, they're coming toward us.
Carb 1: Yeah, and you know, the closer they get, the better they look!
Carb 2: Yeah, that one in front is not nearly as fat as I thought at first. In fact, that one looks pretty darn good.
Brom 2: Hello, carbons! May I have a piece of your pi? (Bromine 2 waggles its nucleus at the carbons.) I have 35 protons! (Bromine 2 tosses its electrons back to Bromine 1 at the same time as both of the carbons lunge out and grab Bromine 2.)
Carb 1 and Carb 2: (Fighting over Bromine 2) Yeah, come here! I'll take this one. Step aside; you bother me! My bromine! My protons! Keep your electrons off! You can have the other one!
Brom 2: Carbons! Carbons! I love you both dearly, but one of you will have to let go! This is simply not comfortable. I feel altogether too positive with my electrons spread out between two of you.
Carb 1: (to Carb 2) You let go! Bromine doesn't have enough charge for me with you hogging half of it!
Carb 2: Why should I be the one to let go? I don't want to be a carbocation!
Carb 1: Well, why should I be the carbocation? I'm a secondary carbon the same as you!
Brom 2: Will one of you please let go?!?
Brom 1: (to Bromine 2) Hey, Bro, if you let go of one of them, I'll grab it.
Brom 2: I can't let go! They won't let me! Save me! (Bromine 1 tries to come in but can't get near enough to the carbons to help because Bromine 2 is in the way.)
Brom 1: Move your fat orbitals!
Brom 2: I can't! Try coming at them from behind. (Bromine 1 goes behind the cyclopentene.)
Brom 1: Okay, Carbon. I'm right behind you. Let go of my Twin and grab me.
Carb 2: No! No! No! I don't want to be a carbocation!
Brom 1: You won't be a carbocation, you idiot. We'll do a nucleophilic substitution. Just grab a pair of my electrons and let go of my Twin's electrons at the same time, and you'll be okay. (Carbon 2 does this.)
Brom 2: Oh, that's much better. Well, here we are, a cycloalkyl bromide!
Carb 2: Excuse me, but we're more of a bromocycloalkane.
Brom 1: (scornfully) Oh, goody, an IUPAC perfectionist.
Brom 2: Gosh, do you realize we were a bromonium ion just for a little while there? I was in a bromonium ion!
Brom 1: That's not something I would let get about, especially to other halogens. They might think you have a thing for a low electron density. You should just be quiet about it. You never know where there might be some chlorine lurking about.
Brom 2: (Looking anxiously over its shoulder) Oh, you can't scare me, you fat chunk of fluorine bait.
Brom 1: Boy, am I glad this is a trans arrangement.
Carb 1: Will you two settle down? We wouldn't have bonded with you if we had known you were so energetic!

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Adorable Borane

(How Three Propenes Were Led Into Ruin by a Handsome Nucleus)

Characters: The characters include the Primary (Prim 1) and Secondary Carbon (Sec) of a propene, the Primary Carbons (Prim 2, 3) of two other propenes, the alluring Boron (Bor) and its three Hydrogens (Hyd), the evil Peroxide ion with its Oxygen (Ox 1), and the water molecule, with its Oxygen (Ox 2).

 Sec: (Sigh) I'm a little tired of this pi bond, aren't you?
Prim 1: Yes, it is a bit of a strain.
Sec. What we need is a nice pair of little hydrogens. Then we could settle down with some comfortable sp3 orbitals and enjoy the bliss of saturation.
Prim 1: (Seeing the borane) Look at that! What kind of atom is that??
Sec. Why, that's a boron! You don't see too many of those.
Prim 1: Just look at that nucleus! I would share electrons with that any day!
Sec: Just a sextet of electrons, and Boron can barely even hold on to them. Those hydrogens are practically ripping those electrons away. Can you imagine?
Prim 1: (to Boron) Hey, you cutie! Look what we've got. (Carbons wave their electrons at the Boron, who drifts over.)
Bor: Nice electrons, carbons.
Prim 1: Bond with me, gorgeous.
Bor: I'm not really interested in bonding right now, but I would like to get to know you better. (Boron sidles up close to Prim. Primary pulls the shared electrons closer to itself, leaving Sec a little bit delta positive.)
Sec: Hey, you two! Don't take all the electrons. I feel naked.
Hyd: You look positively marvelous! Here, take my electrons. (Hydrogen yanks its shared electrons away from Boron and thrusts them at Secondary, who grabs them, at the same time letting go of one of the electron pairs shared with Primary. At the same instant, Primary hands the newly released electron pair to Boron, who takes it.)
Prim 1: Got you!
Bor: No, I got you!
Sec: Hello, Hydrogen. Do you like my orbitals? I was just saying to my bond-mate here, 'What we need is a cute little hydrogen to bond with,' that's what I was saying. And here you are!
Hyd: Do you always talk this much?
Sec: It excites me when I hybridize my orbitals.
Bor: Well, that's one. Now for another one. (Seeing another propene:) Hi, carbons!
Prim 1: What do you need them for when you've got me?
Bor: Well, in case you haven't noticed, I still have nothing but a sextet. You may be satisfied, but I'm not! (The second propene approaches.) Nice electrons, carbons.
Prim 2: What are you doing with that propane? It doesn't have anything to offer you.
Bor: No, but you do! Let me just admire your electrons. (Prim 2 starts to reach for Boron.) No, no, you naughty carbon. No bonding! (Boron's second Hydrogen jumps
to the second propene, and Boron ends up bonded to Prim 2.)
Prim 2: (satisfied) How do you like those electrons?
Bor: Very nice! Now all I need is one more.
Prim 1: I don't like this. There's something screwy going on around here.
Bor: (to 3rd propene) Hi, there, you big hunk of electrophile bait!
Prim 2: Hey, what's with you? Two propanes aren't enough for you?
Bor: You're all used up, and I'm still not satisfied.
Prim 3: Nice nucleus, boron! What are you doing hanging on to those two lumps of hydrocarbon?
Bor: Oh, they're nothing. It's you I want.
Prim 3: Well, take a grab of these electrons.
Bor: No, I don't actually want to bond...
Prim 1 and Prim 2: Don't believe it! Watch out for that Hydrogen!
Bor: Too late! (Boron's last hydrogen hops over to the third propene, and Boron grabs Prim 3's electrons.) Now I've got you, you three suckers! (Boron shouts to someone offstage:) You can come in now. I've got them! (A peroxide ion and a water molecule come in.)
Prim 3: Oh, no! It's... it's a peroxide! They shed oxygens the way children shed lice!
Prim 2: We're doomed. I don't like bonding with oxygens. They are the worst electron hogs! (The peroxide molecule advances on the organoborane.)
Bor: In here, Oxygen. (Boron grabs Oxygen 1 and puts it between itself and Prim 1. Boron then grabs the remaining hydroxide molecule.)
Ox 1: Hello, pal! Nice electrons. Don't expect to see much of them! Heh, heh!
Bor: Hurry up, water! Get this over with. I don't like having a negative charge!
(Oxygen 2 from the water hands its hydrogen over to Oxygen 1, keeping the electrons. Oxygen 1 immediately lets go of Boron.)
Ox 2: What's in this for me, I'd like to know?
Bor: Just stick around. You'll get your chance. (The organoborane and the left-over hydroxide exit in a struggling huddle.)
Sec: Look at us. We're a lousy propanol. I never thought I'd see the day when I would be part of an alcohol molecule.
Hyd: I'd rather be bonded to you than to that rotten Boron. I tried pulling my electrons away, but I couldn't quite do it.
Prim 1: That was a set-up. We were tricked.
Ox 1: Yup, that handsome little Boron does the trick every time.
Prim 3: Who would have thought that a cute little electrophile like that would be so wicked? Led us right straight into the gutter!
Ox 1: Yeah, and the Boron got me the Primary Carbon, no less! It's the best system I know. Gets around that old Markovnikov rule.
Sec: (huffy) But really! I was still almost a carbocation!
Ox 1: Who cares? I'm happy. Let's go contaminate some ethanol!

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