Recently in Contests & Challenges Category

If you recall, the winners of this contest were chosen by pulling cards out of a hat, an unusually large (size 7 3/4") black top hat. The questions asked by the winners* were:

1. Fluffy C. - Are the low reactivity of bromocyclohexane and bromocycloheptane towards NaI due to the way the rings fold?
2. Ross Y. - What is the relationship between angle strain and S_N1 reactivity in cycloalkyl bromides?
3. Kelsey W - Why is 3-bromocyclohexene more reactive than bromocyclohexane towards NaI?

These are all great questions and none of them have obvious answers so its a good thing I wasn't forced to answer them on the night of the contest.

I've received lots of emails this weekend about the lab report. Most of asked whether there were typos in the list of compounds. There were and thanks to all who pointed them out!

• 2-bromopropane should have been 2-bromobutane
• 1-bromo-2,2-dimethylpropane is missing from one list :-(

I'll correct these errors when I can get near the web server for the lab manual (tomorrow), but neither of these errors should interfere with your ability to write a lab report. Remember, you only need to include three compounds in your description of a reactivity trend (although you are welcome to include a few more). Just work around the missing compounds, OK?

Contest is optional. The lab report indicates that a contest entry is required (that was my original intention). Please enter the contest only if you want to. I know that these last few weeks of the semester are an incredibly busy time for everyone. The contest is mainly for entertainment purposes (although I will make a determined effort to answer the winning questions), so please enter only if your schedule permits.

The final week of the C7 H10 O3 contest brought in two entries. Gabe Holt and Patrick Fink had submitted an entry during week #1, but all of the other participants were brand new, bringing the total number of participating students to 19 (one-third of the class).

Unfortunately, neither team could come up with an isomer that had been described in the scientific literature so we don't really have a "winner" in the usual sense this week. However, in the event of a tie, the judges (me) have decided that the runner-ups will split the usual prizes, so everyone will go home with half of a milk chocolate truffle pig. Enjoy. Here are the structures that were submitted this week:



And since you are probably dying to know what the best-studied isomers look like,

The C7 H10 O3 contest continues with three new entries. The winning team nearly hit the jackpot: 140 references. Congratulations Orissa and Rachel !!

The other teams submitted molecules that looked pretty interesting to me, but I guess organic chemists haven't had a chance to study them yet. No hits.



The contest continues with the same rules for one more week:

The rules for entering the contest this FINAL week: any 3-5 people in the class may combine on an entry and turn it in to me by lab lecture next Th (Sept 25). Just draw an isomer of C7 H10 O3 on a piece of paper, add your names, and you're in! There are two constraints: winners from weeks #1 and #2 should not re-enter (give others a chance!) and I won't accept multiple entries from the same person.

Week #1? Yes, that's right. Last week's contest brought in only three entries and the results were so intriguing (see below) that I thought it would be fun to extend the contest two more weeks. So I will collect entries this coming week and name a new winner, and then I will repeat the entire process the following week. So you have three chances to win in all.

The rules for entering the contest this week are identical to those from last week. Any 3-5 people in the class may combine on an entry and turn it in to me by lab lecture next Th (Sept 18). Just draw an isomer of C7 H10 O3 on a piece of paper, add your names, and you're in! There are two constraints: winners from this week should not re-enter (give others a chance!) and I won't accept multiple entries from the same person.

OK. So what did this week's entries look like and who won?