Leading Question


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Leading Questions How will that ring open and, more importantly, can you stop playing??
The Cleavage	The Reductive Cleavage
Background: You downloaded Trivia Crack yesterday. Actually a week ago. But it feels like yesterday. You wouldn't know because you've been playing for 168 hours straight. It's time for you to stop, your family misses you and your girlfriend is upset that she can't win. You should probably stop. No seriously.	Background: Your super cool SSG leader let you out like an hour and a half early with pizza but this time gave you homework, again, ugh. He gives you Molecule 44 and asks you to "explain why the cyclopropane ring is susceptible to reductive cleavage, but the other rings in starting material 44 are not."
The Problem: You're addicted. You know you should stop. You're getting kind of hungry and you might not be able to blink any more. But that jerk with the green smiley face icon just challenged you again and you know you can't let him win. Game on.	The Problem: There's like 5 rings to choose from and they're all different. One is a cyclopropane, one is a normal cyclohexane, one is a cyclopentane ether, one is a cylohexane ester, and there is one of those crazy bicyclic rings that gave you nightmares for a month. How can you possibly pick one and explain why the bonds will break?
The Solution: You've done it, you beat the green smiley guy, again, for the 50th time. You love beating him, but you need to challenge him again. You need to win more. You go to challenge him again, and oh, what's this? An advertisement? It doesn't matter you see ads all the time, but it's Kate Upton, again. You love this ad, you can't help it, but this is like the 100th time. I mean you've already downloaded this game too. It's too much, you've grown tired of her, instead of suffering through you rage quit. After turning off your phone you realized what you've done. You are free.	The Solution: You know organic chemistry. You've been to every lecture this year and really paid attention, sort of. You've learned enough to know that the cyclopropane ring is the ideal site for reductive attack on this molecule due to the strain in the 3-membered ring. The three membered ring is attached to a six membered ring, which puts strain on the cyclopropane because it would prefer to have bond angles of approximately 109.5 degrees, but a three membered ring would have bond angles of 60 degrees. Also speaking in terms of hybridization, sp3 bond angles are supposed to be 109.5 degrees, but in a three membered ring the bond angles are 60 degrees, so there is a lot of strain that makes the rings want to return to the optimal angle orientation, so the reactivity is very large in three membered rings. Wow, look at you, you know your stuff, don't you. Or at least you kind of do. These guys helped you out a bit: Wolk, J. L; Rozental, E.; Basch, H.; Hoz, S. J. Org. Chem. 2006, 71, 3876-3879.
The Result: As far as chemistry goes, the propane ring is the only ring with enough strain to warrant reductive cleavage into two methyl groups. Kate Upton also helped you kick your addiction to Trivia Crack so that you can finally move on with your life. Maybe you can start that HTML project you were supposed to start last week. Just don't open that app agai-Oops. Too late.

Leading Questions

How will that ring open and, more importantly, can you stop playing??

The Cleavage

The Reductive Cleavage

Background: You downloaded Trivia Crack yesterday. Actually a week ago. But it feels like yesterday. You wouldn't know because you've been playing for 168 hours straight. It's time for you to stop, your family misses you and your girlfriend is upset that she can't win. You should probably stop. No seriously.

Addiction

Background: Your super cool SSG leader let you out like an hour and a half early with pizza but this time gave you homework, again, ugh. He gives you Molecule 44 and asks you to "explain why the cyclopropane ring is susceptible to reductive cleavage, but the other rings in starting material 44 are not."

The Problem: You're addicted. You know you should stop. You're getting kind of hungry and you might not be able to blink any more. But that jerk with the green smiley face icon just challenged you again and you know you can't let him win. Game on.

The Problem: There's like 5 rings to choose from and they're all different. One is a cyclopropane, one is a normal cyclohexane, one is a cyclopentane ether, one is a cylohexane ester, and there is one of those crazy bicyclic rings that gave you nightmares for a month. How can you possibly pick one and explain why the bonds will break?

The Solution: You've done it, you beat the green smiley guy, again, for the 50th time. You love beating him, but you need to challenge him again. You need to win more. You go to challenge him again, and oh, what's this? An advertisement? It doesn't matter you see ads all the time, but it's Kate Upton, again. You love this ad, you can't help it, but this is like the 100th time. I mean you've already downloaded this game too. It's too much, you've grown tired of her, instead of suffering through you rage quit. After turning off your phone you realized what you've done. You are free.

Kate Upton

The Solution: You know organic chemistry. You've been to every lecture this year and really paid attention, sort of. You've learned enough to know that the cyclopropane ring is the ideal site for reductive attack on this molecule due to the strain in the 3-membered ring. The three membered ring is attached to a six membered ring, which puts strain on the cyclopropane because it would prefer to have bond angles of approximately 109.5 degrees, but a three membered ring would have bond angles of 60 degrees. Also speaking in terms of hybridization, sp3 bond angles are supposed to be 109.5 degrees, but in a three membered ring the bond angles are 60 degrees, so there is a lot of strain that makes the rings want to return to the optimal angle orientation, so the reactivity is very large in three membered rings. Wow, look at you, you know your stuff, don't you. Or at least you kind of do. These guys helped you out a bit:

Wolk, J. L; Rozental, E.; Basch, H.; Hoz, S. J. Org. Chem. 2006, 71, 3876-3879.

Bond Angles Diagram

The Result: As far as chemistry goes, the propane ring is the only ring with enough strain to warrant reductive cleavage into two methyl groups. Kate Upton also helped you kick your addiction to Trivia Crack so that you can finally move on with your life. Maybe you can start that HTML project you were supposed to start last week. Just don't open that app agai-Oops. Too late.