Ten Thousand Hours

I was talking to one of my roommates the other day, and he told me that he read somewhere that it takes 10,000 hours of work to be considered a master at something.

Ten thousand hours? Goodness. That’s a long time.

If you worked toward that goal 24 hours-a-day, it would take 1 year, 51 days, and 16 hours.

Although, if you choose to spend 8 hours a day, the length of a regular work day, edging toward becoming a master of one thing, it changes to 3 years, and 155 days.

Every single day, spending 8 hours learning about one topic. ONE thing. Could you do that?

I haven’t quite figured out whether I can or not. Much less what I could spend 10,000 hours learning about.

I’m not sure I’d be able to find a topic that I could focus on, or would even still be interested in after spending eight hours everyday learning about it. It might be just be a trend of the younger generations, but an attention span of eight hours a day for 1,250 days would probably be difficult for most people.

I was shocked when my roommate told me this and I’m still sitting here trying to process it. 10,000 hours. Doesn’t that number seem impossible?

Pick one topic. Your favorite, or something you don’t know about at all. Could you learn about it for ten thousand hours? What about one hundred hours? Somehow, even one hundred hours seems like a stretch. But, of course, when faced with a decision like this you don’t want to pick a topic too narrow because then you would run out of things to learn about. Although picking a topic too broad also presents its own set of problems.

I love reading. Could I spend hour after hour reading one book or one author? I think that might be possible. However, once I consider that point as my way to tackle the 10,000 hour question, other questions start popping up. Do you start with a certain genre? Or from the beginning and read through the alphabet? Authors from A to Z?

The truth is, as much as I love reading could I really read 10,000 hours worth? I probably have if you add up all my late nights spent with a page turner. Although, I would not label myself as a master. Would I still enjoy reading if my goal was to spend 10,000 consecutive hours doing so?

There is a very large potential for coming to hate it and seeing reading as a job. I also find that my mind is rebelling at the idea. The time I spend with a book is sacred. It is my get-away. I don’t think I could risk the wonderful relationship that I have with reading to test this theory. I also highly doubt that I could find anybody to pay me for over three years (or longer) just to read books.

So, as I sit here and ponder the possibilities of what I could become a master of with ten thousand hours of experience/knowledge I’d say the possibilities are endless, but are they really?

Obstacles

This blog won’t be about organic chemistry. It probably should be, but it won’t. It might have some stuff thrown in there about organic but I doubt it. This one is going to be about my person. No, not my significant other or the person that means the most to me. My person is the person that put me through some tough experiences and left me to decide and face the outcome on my own.

She is my obstacle.

She is the one that stands between me and where ever I want to go, or who ever I want to become. She stands in my way.

It’s up to me to get rid of the feelings I have and move on but frankly, I don’t know how.

It’s a burden. She’s a burden. On my mind. On my attitude. On my perspective on life.

She taught me that there is bitterness in the world. And that there can be bitterness in my heart. That even though we can be friends and you will put me through some tough stuff (and I’m sure I put you through some too) but the minute it doesn’t work for you, you’re out.

But I can’t think about what’s happened because in the big range of plans, does it really matter? It’s a burden I carry but does everybody else need to feel or know or hear the frustration that I feel when I tell them about the situation?

Everybody has a burden right? Then why should mine be any worse or any different than anybody elses?

If you knew the situation you’d probably tell me that it isn’t that big of a deal and I should move on. But I can’t. She’s my obstacle. She’s what I have to get over. She’s what I have to forgive before things can move on.

However, it’s almost been six, so how could I not have moved on since then? It wasn’t a death or a massive accident or something horrific. It’s just something that hurt me.

How do you forgive? How do you forget? How do you come to terms with what happened and not be moved or upset about it?

I’m still trying to find hand and footholds in the side of the cliff of forgiveness to somehow reach the peak for peace.

I used to think that I wasn’t going to have a burden and I was a little bit worried about it. I didn’t want to be that spoiled brat that had everything she wanted, and I didn’t. Don’t get me wrong but I feel like you can tell the difference between someone who has a burden and someone who doesn’t. Now that I have one, it sucks to have to carry it around everywhere. But where can I leave it? Where do you leave the burdens you don’t want?

Forgiveness. It’s a learning process and I seem to be stuck at step number one.

Building Blocks

When I was a little kid I loved to play with legos. I could build anything I wanted! I remember this one Christmas where my parents gave me this huge crate full of legos that were all different colors and I swear it had over 1000 pieces. It was the best present ever!

I figured something out the other day. Everything in organic chemistry is a building block. I mean everything. A single carbon is a building block that we can use to build/create something else. Too crazy.

I guess it’s kind of like life though. We start out as kids trying out every little thing in the universe and now we’re using those really early principles that we learned in everyday life.

It makes me wonder was what the first thing I learned? To see? To feel? To hear? Did I actually learn those things or did it just happen that way?

I’m assuming I learned it, but whether I was in the womb or not when I learned it is the question. But we all learn different things at different times. Like I will always be inept at playing video games, any kind of video game, but my brothers? Just give them five minutes and they’ll figure out how to play anything.

As for organic chemistry, I started out learning about a benzene ring and then I learned how to put different groups on the benzene ring and now I’m learning how to put something on the benzene ring and turn it into something that reacts with tons of different things and even after that I can use it to make the reaction go further. It’s so cool! (Don’t worry, I still hate it though.)

The thing I learned how to make on a benzene ring and then have it react with plenty of different reactions is the diazonium salt.

The molecule to the right is the diazonium salt. Let me tell you how you can make it.

1. Take a regular benzene ring and react it with HNO3 and H2SO4. The result of that reaction is a benzene ring with an NO2 group coming from it.

2. React that with Sn/HCl and that reduces it down to a benzene ring with an NH2 group coming off of it. It’s name is aniline.

3. React aniline with NaNO2 and HCl and you get the diazonium salt.

You have to immediately react the diazonium salt with something. You can’t isolate it.

Now for all the reactions you can react with the diazonium salt:

1. React the salt with BF4 to get a benzene ring with a flourine on it.

2. React the salt with KI to get a benzene ring with an iodine on it.

3. React the salt with CuCl to get a benzene ring with a chlorine on it.

4. React the salt with CuBr to get a benzene ring with a bromine on it.

5. React the salt with H2O to get a benzene ring with an alcohol on it.

6. React the salt with an alcohol (ROH) to get a benzene ring with the OR group on it.

7. React the salt with H2PO3 to take it all the way back to a regular benzene ring.

8. React the salt with CuCN to get a benzene ring with a cyanide group (CN) on it.

So many reactions, so little time. But it’s all just a building block for something else right?

The Eraser

Have you ever just wanted to disappear? Felt so embarrassed you just wanted to sink into the ground and never reappear again, because you knew that someone was going to bring it up and you were going to be embarrassed all over again. Do you remember those memories years after they’ve gone by? Do they still make you turn red and shake your head? I have some memories that still do that to me.

Why?

They’re not defining moments in my growing up stages. I have this one that just keeps on popping up right when I don’t want it to. It is usually after some other embarrassing moment that has just happened and it never fails to make me feel stupid. Want to hear it? Okay, good, because I want to tell it. Well not really but maybe that will make it stop coming around.

Every year when I was growing up I used to spend a week at a summer camp. Every year at that summer camp each of the different cabin groups had to do a skit at the end of the week. Now, these cabin groups were usually made up of one boy cabin and one girl cabin that spent the week together doing different activities. Well, one year our cabin group decided to do a song. A friend and I had small different speaking parts in the song and every time we practiced she and I both got it right. Except for the night of the skit. She said her line in both slots instead of her in hers and mine in mine. Well, that night meant a lot to me, I couldn’t tell you why now but I was so embarrassed and it wasn’t even my fault.

I tell myself that it wasn’t and isn’t that big of a deal, nobody noticed and to move on. So why does it keep coming back to ‘haunt’ me every time I seem to make a mistake?

I wish I could just erase it from my memory or at least erase the feelings of my embarrassment.

Did you know that organic has such an eraser? It only works for organic reactions but I still like to think of it as an eraser.

This eraser can get rid of unnecessary ketones and just cut them down to hydrogens. Neat right? Now only if it worked in my life.

Imagine if you were trying your hardest to put this product together and to get that perfect result but you can’t seem to get rid of this ketone! Boy do I have a solution for you!

It even has two conditions you can use it under so you can be able to do it when you need to!

I guess it’s about time that I gave you the reactants isn’t it?

Well for acidic conditions I would use: Zn(Hg), HCl. However, these reactants will react with an alkene so if there is one and you don’t want it to go away use the basic conditions.

This is an example of the reduction using acidic conditions:

The Wolff-Kishner reaction is another name for the reaction under basic conditions. Those reactants are: H2NNH2, KOH and heat. Now if I were to add the Wolff-Kishner to a product that I wanted reduced which also happened to have a bromine on it, I would be in trouble because those two react.

This is an example using the Wolff-Kishner:

Now that we all know of an organic eraser I think it’s time that we come up with one for bad memories.

Who Needs Limitations?

Per the title, what do you think needs limitations?

I found out today that my bike tires have limitations. I don’t know how long those tires have been on that bike but they needed some lovin’ today. However, I got it up and running in no time. I had to get home some how!

Anyways, who needs limitations? I wish I didn’t have any. The ability to stay up for days with no sleep would be highly beneficial during exam time.

But, I am here to tell you that organic chemistry has limits.

Who knew! I didn’t, well maybe I did, but you always expect the big things in life to not have limitations. So when my professor told the class that the Friedel-Crafts reactions had limitations, it took me back a step. I mean yeah, we’ve had reactions before that were defined by the limitations it had but I hadn’t really expected this set of reactions to have limitations. Without the limitations I could have done anything with those reactions! Well, I would have needed a few others but still!

Now that I think about it organic chemistry is defined by what it cannot do.

Seriously. Think about it.

We may have these awesome ideas about how to cure cancer or something equally amazing, and we can try our hardest to make it work or try to find something that works but it’s all about what doesn’t happen. Which routes we can’t take. All of which we learn from but I’ve got to admit, it frustrates me sometimes.

Limitations! I don’t want them!

Such is life, I know, I know. But! Before I get further off topic and wander around in the wilderness a bit, let me tell you about these two limitations to the reactions.

First for Friedel-Crafts Alkylation only, you can’t control whether there are going to be rearrangements on the Super Electrophile or not. So you always have to be aware of the possibility of rearrangements.

Now the second one is for both reactions.

Second, neither reaction will work if the benzene ring is deactivated. Deactivated meaning, with an electron withdrawing group on the benzene ring. Well then what’s an electron withdrawing group? Anything that pulls electrons away from the benzene ring. Like NO2, CF3, other carbonyl compounds, NR3, CBr3, CCl3. The list goes on for a little bit further but I think you’ve grasped my point of withdrawing groups.

Now that I’ve told you about these limitations. Can you think of others out there in organic or your life? Just by writing this I’ve found some interesting limitations in my life. Like I’ve never ridden on the city bus system. Now, I may not call that a limitation but it is something that keeps me from having a broader range of experiences.

Additional Steps

There’s another part to the Friedel-Crafts set of reactions. Want to know what it is?

Didn’t think so. I didn’t want to either. If I hadn’t started being a good student and attempting to read the book before class I’m almost positive that I would’ve groaned out loud at the professor’s statement of there’s more!

One can always hope that we’ve been taught the last reaction in the book but it’s never going to happen I imagine.

Sadness.

Anyways, the other half of the set of the Friedel-Crafts reactions is called:

Friedel-Crafts Acylation. Ta-da! Impressive right? I bet you can’t say that five times fast. Ok, maybe you can but still.

With this reaction you can add carbonyl compounds to the benzene ring.  Which, in the real world is probably really important. In the imaginary word of my notebook paper in organic it’s a good reaction to know too.

For the reaction that I’m going to show you how to do we’re going to use an aldehyde and instead of a hydrogen one side of the carbonyl there is going to be a chlorine.

We’re going to be using a Lewis Acid with this too. What do we use it for? To get the carbonyl to react by creating…. A Super Electrophile! Yeah, once again we do it but maybe it’ll be over soon.

To begin the reaction,

1. A lone pair of electrons on the chlorine attack the aluminum in the AlCl₃. This gives the aluminum a negative charge and the chlorine a positive charge because it is still attached to the carbonyl.

2. The bond pair of electrons now go on to the chlorine to get rid of its positive charge and giving the carbon attached to the oxygen a positive charge. There ends up being resonance on this compound. Can you find it?

3. Getting rid of the chlorine also makes the carbocation very reactive so very soon after that, one of the single bond pair of electrons that make up the double bonds in the benzene ring come and attack the positively charged carbon.

Can you tell me what this creates?

That’s right a cyclohexene with alternating double bonds and a carbocation on one carbon and the carbonyl and a hydrogen on the other carbon that don’t have a double bond between them.

What happens now?

4. A lone pair of electrons from one of the chlorides attached to the aluminum attacks the hydrogen attached to the carbon and the electrons in the carbon-hydrogen bond go down and form the lacking double bond in the benzene ring.

What do we have now?

A finished project!

Awesome! Congratulations!
I hate to bring this up but a vocabulary lesson is needed. The carbonyl compound with the chlorine on it is called an acid chloride. It looks like this:

You could also use an acid anhydride with a Lewis acid and get the same result. An acid anhydride looks like this:

Isn’t vocabulary fun?

Yeah, I thought so too. Well, if you learn it now you won’t have to re-learn it later.

But thankfully that’s all the parts to the different Friedel-Crafts reactions… at least until we get to the limitations of those reactions but those are short.

Want to Add Color to Your Clothes?

When I was in high-school I always used to think that it would be cool to tie-dye clothes or wear insanely bright-colored t-shirts.

Now that I look back on it, the security that I had to do that in high-school is amazing. Sometimes I wish that security could follow me around and serve as a buffer between the world and me. Although, I would never have the experiences that I do now if that buffer followed me everywhere.

Anyways, back to the topic at hand. I was doing some research for the reaction that I wanted to tell you about today and I found out that the reaction is used in making kinds of bright dyes. Neat right?

I do have this inane feeling that having this knowledge is going to send me into a tie-dye spree of all things white but maybe spelling out all the steps like I usually do will squash that feeling before I go broke feeding this urge.

This reaction is called Friedel-Crafts Alkylation.

This reaction is where we would take a regular old benzene ring and attack it with something that has a carbon chain or anything just as long as there is an electronegative element on it so we can make a Super Electrophile out of it.

Yeah that’s right, I said Super Electrophile again. It’s what benzene reacts with! Or maybe, it’s what I love to do and talk about. Ha, yeah right. I’m hoping that we’re going to learn something different in organic just so I can have something different to talk you about but I think the next thing is all about ketones and aldehydes. So, I’ll be happy with what I’ve got now.

On to the reaction before I get too much off topic again.

To keep the reaction simple I’m going to use methyl-bromide (CH3Br) and a benzene ring. As the solvent to get the reaction to work I’ll use AlBr3.

1. To start, a lone pair of electrons on the bromine attached to the methyl attacks the aluminum. This creates a negative charge on the aluminum and a positive charge on the bromine because it has two bonds.

2. The bond pair electrons between the methyl and the bromine then go on to the bromine to form AlBr4 and a CH3. The methyl group is now our Super Electrophile because it has a plus charge.

Now we can complete the rest of the reaction.

3. One of the single bonds that make up the double bonds of the benzene ring attacks the positive carbon. This makes the same cyclohexene we’ve seen for a while with alternating double bonds and a plus charge on one carbon and the methyl group and a hydrogen on the other.

4. A lone pair from one of the bromine’s on the aluminum attacks the hydrogen on the benzene ring and the carbon-hydrogen bond electrons reform the double bond and thus recreates the benzene ring with all its stability.

5. The positive bromine now leaves the aluminum to form HBr and AlBr3 as side products and we end up with a wonderful methyl-benzene as our main product. Otherwise know as toluene.

Pretty right? Well we did the hard work for it to be that pretty. Now the compound that is in the different kind of dyes looks like this:

Now that’s what I call complicated. Especially for one reaction. But totally cool at the same time.

I feel the need to put in a disclaimer so here goes.

Disclaimer: Do not try to use either reaction to make dyes. It is only one of the reactions that is needed to elicit a dye that you can dye your clothes in.

(Pardon me. I seemed to have made a mistake. The reaction above is actually an Friedel-Crafts Acylation experiment. I talk about that reaction in the next blog ‘Additional Steps.’ Please excuse the mess-up.)

Beautiful Furniture

Have you ever walked into a house and your first thought be, “Those are gorgeous floors?” They have that perfect sheen on them and you can tell that a silly puppy hasn’t been running through that house at all. It’s almost like you can see your face in the floor if it was lit from behind.

I can’t say I’ve seen too many houses with floors like that but when I do it simply takes my breath away.

The one thing I do know that has the layer after layer of varnish on it is my family’s dining-room table. It’s breathtaking.

It’s been handed down from generation to generation and the legs on that table are so beautifully carved that when I’m bored over Thanksgiving dinner I am perfectly content to sit there and just run my fingers over the different groves in the wood.

Well you’re probably wondering what this has to do with organic chemistry. And as I found out a little while ago, nitration, which is (of course) a reaction in organic, is actually a side product that comes from the different oils mixing together and actually generating a thicker varnish. Which might be a pain to paint with but a joy to look at after its done.

The way nitration happens with a benzene ring (of course) is that we always have to make the Super Electrophile to react with the benzene so lets hop to it!

The reactants in this reaction are HNO₃, benzene, and the solvent is H₂SO₄.

So, to create the Super Electrophile:

1. A lone pair of electrons on the oxygen of the hydroxyl group go and attack one of the hydrogen’s on sulfuric acid. The bond electrons between the hydrogen and the oxygen are then switched to the oxygen to give the oxygen a negative charge.

2. The oxygen that has the negative charge that is attached to the nitrogen then pulls a lone pair of electrons down to form a double bond between the nitrogen and the oxygen. That move kicks off the oxygen that has two hydrogens and thus removing water and making the nitrogen positive at the same time. It’s probably gross water but hey, it’s water nonetheless. Look at the mechanism to the right to see how we would make the Super Electrophile!

Now that we’ve made it to this point it’s only just a little bit further to get to the end point and to see what makes that oil seem to pull out the grain in the wood and make it sparkle.

3. Now, one of the single bonds that make up the double bonds in the benzene ring attack the nitrogen with the plus charge in the Super Electrophile. This then makes the cyclohexene with two alternating double bonds and on the two remaining carbons, one has a plus charge and the other has a nitro group on it as well as a hydrogen.

4. The oxygen that lost a hydrogen in the beginning now makes its comeback and attacks the hydrogen attached to the carbon with the nitro group and the hydrogen-carbon bond electrons go into making the benzene ring complete again.

Next time you see a house with floors or a piece of furniture that has such a wonderful glossy finish I hope you’ll speak up because the tender love, and care for such a piece of beauty is most definitely a treasure to behold.

What’s in Your Detergent?

Last night I had one of those dreams of being naked in school and everybody laughing at me. I think you know which one I’m talking about. Have you ever had one of those?

That dream spurred me in to do laundry today. Just to make sure I wouldn’t have an excuse to end up in school naked. Good idea right? I thought so too.

Well while I was pouring in the laundry detergent, along with the softener, and trying to cram in most, if not all, of my dirty clothes in the washer. I started to wonder… what’s in laundry detergent?

It’s kind of one of those things I don’t really think about, but once the topic is brought up I can’t really help but try to figure it out. I tried to forget about it! I promise! It just kept coming back and back, so I gave up and did a little research.

What I found wasn’t really all that surprising, especially when your life is spent with organic. I’ve pretty much just stopped being surprised when it shows up in the most random places.

I mean detergent! Really?

I guess it makes sense though, because detergent is made out of molecules that are hydophillic (likes water) on one side and hydrophobic (can you guess what this means?) on the other. Essentially, it means that the detergent has the power to come in and pick up that dirt and grime from your clothes with the hydrophobic side and carry it away. And hopefully, right on down the drain

Think about it, if dirt liked water, it would be washed away with the tiniest droplet it.

That spaghetti sauce you spilled all over your dress on the first date? Gone. In the blink of an eye.

Sweet right? Well, one can dream.

Anyways, I was looking through the pictures of some of the compounds that are in detergent and came upon a molecule I know how to make now! In second semester of Organic Chemistry! Awesome!

I wouldn’t really call it awesome but I feel the need to share with you the process in which this could happen.

The most wonderful, original, amazing name of this process is….

Sulfonylation (Original right?)

On a cool note though, this reaction is reversible. Even though this may not be that huge of a deal to you, not many benzene reactions (that I know of at least) can be reversible.

On towards greatness!

1. You start out with a regular old benzene ring. It won’t be regular for much longer though! And you have the option (don’t we all love options!) to chose between concentrated sulfuric acid (H₂SO₄) and fuming sulfuric acid (SO₃, H₂SO₄).

2. Now we have to make a Super Electrophile! It’s almost the same mechanism as the Halogenation one that I explained in the last blog I wrote but I’ll rewrite it again just for kicks and giggles. Nah, it’s because I love doing it. Promise.

I’m going to pick concentrated sulfuric acid to work with tonight.

3. To form the Super E, one of the lone pairs of electrons on one of the oxygen’s that form the two hydroxyl groups on the sulfuric acid attacks the hydrogen on a different sulfuric acid hydroxyl group. The electrons of the hydrogen-oxygen bond then go over to the oxygen and make that oxygen have a negative charge.

4. Now the hydroxyl group across from the OH₂ group kicks into gear. A lone pair of electrons on the oxygen comes down to create a double bond between the oxygen and the sulfur. This turn of events then sends the electrons forming the sulfur-oxygen bond on the other side of the molecule get kicked off back on to the oxygen. The leaving group ends up being water. I wouldn’t drink it, but it’s still water.

Guess what we’ve completed? The Super Electrophile!

Now to continue on with the rest of the master plan!

5. Now one of the oxygen’s has a positive charge on it because it has a double bond to sulfur and a single bond to hydrogen.  One of the many single bonds that form the double bonds in the benzene ring breaks and attacks the sulfur and kicks one of the bond pair electrons between the positive oxygen and the sulfur back on to the oxygen creating a cylcohexene with a positive charge on one carbon and a SO₃H and a H on the neighboring carbon.

6. Water then comes in and takes off the hydrogen on the carbon with the SO₃H group on it and recreates the double bond to form a fully functioning benzene ring once again.

Like this ——————————————————————>

Now, that is not what is exactly in your detergent but if you added just a few more carbons on the tail end you’d get a wonderful picture of some of the stuff in your detergent.

I now have clean clothes, a renewed sense of security and told all of you about my wonderful experience with the Sulfonylation experiment.

Aren’t you just glad I won’t be going to school naked? Even in my dreams? I know I am!

You Can’t Top a Halogenation

Do you ever have one of those days where you really just don’t want to get out of bed?

Well, I had one some of those feelings this morning.

Can you guess what made me get out bed?

Organic. Well actually, it was having to be at work in 40 minutes, but the thoughts of organic still raced through my brain as I looked at the ingredients on the back of my toothpaste bottle and actually recognized the names of some of the compounds. Amazing right?

Not really, it was actually more like a sinking feeling of ‘I’ve been doing this way too long.’ Alas, here I am to tell you more about it.

Today I get to tell you all about benzene (C₆H₆) and all the wonderful things this compound is capable of, although it might take more than just this blog.

Isn’t that just a lovely picture? Well, it’s actually not a perfect picture because you see, the double bonds alternate patterns so this is only one resonance structure of the compound.

In all reality benzene is a compound that lies flat and the bonds between the carbons actually have half a double bond between all of them. So, it’s like a bond and a half connecting each carbon.

True or false? Is benzene aromatic?

True! It is! The aromaticity actually keeps it even more stable than it would be if it were just a molecule.

There are tons of different reactions you can do. A few of the ones I’ve learned are all about putting different groups on the benzene ring so it can react with other things. To name a few there’s: Halogenation, Nitration, Sulfonylation, Friedl-Crafts Alkylation, Friedl-Crafts Acylation, the list goes on and on and on. I feel like I’m chipping at an iceberg that’s 30 times larger underneath the water.

I guess we better get to chipping.

Halogenation:

Usually when you add Br₂ to benzene you get nothing. Nada. Zip. Zilch. Which ends up being a problem. Not so much in my imaginary world, but here in the real one, BIG problem.

So, to fix such a problem all we have to do is add a Lewis Acid. And for all of you out there that need a little memory jog, a Lewis Acid is a molecule that can accept the pair of electrons that will inevitably chase after it. For Bromination I usually use AlBr₃.

Benzene then throws another curve ball at you. Can you handle it?

Don’t read on if you can’t.

For something to react with the benzene ring it has to be a ‘super electrophile’.  (Insert all those superhero theme songs that you hear in your head right now.)

Now you’re probably asking, “How do we make a super electrophile, Amy?” “Tell me, tell me, tell me!” I’m getting there I promise.

Here’s the recipe for the ‘super’ electrophile:

1. A lone pair of electrons on one of the bromine’s in Br₂ attacks the aluminum in AlBr₃. This results in aluminum with four bromine’s attached to it and another bromine attached to one of the bromine’s on the aluminum. The aluminum ends up having a negative charge and the bromine that has bromine attached to it on one side and aluminum attached to it on the other side has a positive charge.

2. The bromine attached to the other bromine then moves the bond electrons over the bromine attached to the aluminum and you result in a bromine with a positive charge. Which is….

Your SUPER Electrophile!!!!! Yay!!!

Now, that benzene ring that we’ve got hiding behind the curtain can go to town on that super electrophile.

Here’s the rest of the recipe:

3. One set of the bond electrons, from one of the double bonded carbons in the benzene ring (for mechanisms, I use the picture above to help instead of the real form of benzene) attacks the ‘super’ bromine. Which forms a carbocation (carbon with a plus charge). You’ll end up getting a cyclohexene with two alternating double bonds and on one of the two remaining carbons in the cyclohexene is a plus charge and on the other is the bromine and a hydrogen.

Side note: In order to make this possible there ends up being several resonance forms where the carbocation is moved around the molecule. Can you find them all?

4. Now bond pair of electrons that comes from one of the aluminum-bromine bonds goes over and attacks the hydrogen that is attached to the same carbon with the bromine on the cyclohexene. Then the electrons of the hydrogen attack the carbon with the plus charge and make a new double bond between the carbons and you end up with…

Drum roll please……

Woo hoo! We did it!

Now, the same thing goes for chlorine… you should try it! Just put it with AlCl3 or FeCl3.

Phew. That’s enough organic chemistry for me. Tune in for more later because there will be more… there’s ALWAYS more. Hence, why it runs my life.