Weekly Group Review

I think that we should start a group review. I think by going over the material weekly we can get a sense of what's going on.

So if anyone is up for the awesome challenge then comment on this post!


Good LUCK!!


C+

For studying

Literally this website saved my life last semester http://www.masterorganicchemistry.com
Click on resource guide and there's a list of practice exams and different study materials you can use. Good luck to everyone on the test tomorrow!!

Chemistry Seminar: Minorities in Chemistry

I attended the Friday chemistry seminar concentrating on minorities in chemistry.  It was an enlightening experiences due to the four guest speakers present: 1 Latino female, 1 African-American female, and 2 African-American males.  Being a female majoring in biochemistry, the seminar was a great tool for encouragement.  The seminar itself demonstrated the small percentages of women and minorities present in the industry.  Each speaker attested the struggles involved in getting an education, finding a job, and becoming successful as well as the people who might discourage you or prevent you from succeeding.  A piece of advice focused upon during the discussion was the concept of finding a mentor.  This idea seems so obvious but is rarely acted upon. The speakers discussed the valuable information and guidance a 'mentor' can have for a student.  Mentors are able to help students struggling with decisions to be made after graduating and also simply offer directions as to where an answer can be found.  Intimidating as it might seem, introducing yourself to your instructors and finding a connection with one can better yourself in the future and possibly in terms of networking after graduation.

StudyBlue.com

For those of you that have never used this website for other classes, you should definitely check it out.  You can upload notes, make flashcards, and share everything with everyone in your class--or keep your notes private if you prefer.  There is also an app so you can flip through reactions on the go on your phone/tablet if you are in a time crunch :) I made the class, so now all you have to do is click the link and sign up.  I mostly use this app for my anatomy class, but now that we are getting towards the middle of the semester, there are a ton of reactions to remember.  Enjoy studying :)


Study Blue Chemistry 352--Petersen

Sapling assignment

Anyone can help me with problem #20? the problem is benzene + CH2CH2CH2CH2CH2CH3Cl with the present of AlCl3.  The benzene is excess.
Thank You

Six Pillars of Organic Chemistry

I'm writing a short abstract for an article I've found useful in approaching organic chemistry: Joseph Mullins article, "Six Pillars of Organic Chemistry," from the Journal of Chemical Education. To find the article, log into the UNCG website, search for the Journal of Chemical Education, and then search for Full Text Options. This should lead you to the Journal of Chemical Education, where you'll be logged in under a UNCG proxy. Here is the citation for the article:

Mullins, J. J. (2008). Six pillars of organic chemistry. Journal of Chemical Education, 85(1), 83. Retrieved from http://search.proquest.com/docview/212035734?accountid=14604

Joseph Mullins' article "Six Pillars of Organic Chemistry" presents a useful way to approach Organic Chemistry. Mullins suggests that establishing a strong conceptual framework while learning organic chemistry assists students in understanding new material and integrating this material into their existing knowledge. Because the volume of information in organic chemistry can be overwhelming Mullins provides a framework based on six key principles. These six principles are: (1) Electronegativity, (2) Polar Covalent Bonding, (3) Steric Effects, (4) Inductive Effects, (5) Resonance, and (6) Aromaticity. These six principles are chosen for their wide scope and applicability, their ability to interpret information, and their ability to serve as the foundation for other principles or concepts. Mullins discusses each concept and its importance to a general understanding of organic chemistry. Mullins provides visual examples as well as references to biochemistry (presumably due to the importance of organic chemistry in biochemistry). Mullins concludes by discussing how these six principles can be adapted to into course lectures, and notes that discussing conceptual issues in organic chemistry is beneficial outside of organic chemistry courses.

Online Flashcards for Quick Review

Hopefully everyone is well prepared for the test tomorrow.  I'm sure a lot of you like myself use flashcards as a study tool.  I find them very helpful, not just as a review, but also because it helps to reiterate things just by writing it down.  Since they are my own cards though, I have them memorized and it's not always the best quizzing technique.  I know there are a lot of flashcard sites out there as well, but I found this one that I thought is especially useful.  It helps me because you really have to think about what it's asking as opposed to recognizing one side of the card you've done and just repeating what you've memorized on the flip side.  Since I didn't write the card myself, I really have to think about it more than rote memorization.  It's a little bit more like a last minute pop quiz review for reagents that some may find helpful for a last quick review.  Good luck on the test!

http://www.proprofs.com/flashcards/cardshow.php?title=organic-chemistry-synthesis&quesnum=3

Let me know if anyone else has found some good flashcard sites they'd recommend.  There are a lot out there!

NBS Chapter 12

So I'm getting a little confuse about NBS. I want to know if NBS is basically a radical that attacks vinylic and benzylic carbons. Thank you.

Study Tips

Since I did pretty well on the last exam, I thought I would share a few tips that helped me to succeed.

1) SIP is pretty helpful. If you can make it, you should definitely go, especially if you have questions.
2) Go over the sapling problems more than once. I found it helpful to go over the earlier homework problems again closer to the test because I had forgotten some key points that the homework points out. Going over the earleir homework problems helped refresh my memory.
3) Do problems in the book. The more practice you get before the exam, the less time you will waste and the less likely you will run out of time on the exam.
4)Review reactions from previous exams/ last semester. The more reactions you know the better you will do on the synthesis problems.
5) Practice drawing mechanisms. Drawing these over and over can prevent you from making silly mistakes when drawing out mechanisms on the exam.
6) Instead of just memorizing reactions, try to understand why they do what they do. This will help with the multiple choice on the exam.

If I think of anything else. I will add it. In the meantime, I hope these six tips will help.Good Luck!

Section 15.15 from Bruice, Friedel-Craft Alkylation of Benzene

Hi folks,

I had a quick question about the Friedel-Craft alkylation of benzene mechanism that's shown on pages 645/646 of the textbook.  Where it says "Generation of the electrophile," we see that an alkyl chloride becomes a carbocation intermediate when the Cl atom leaves and binds to the AlCl3.  My question is, why does this work for primary alkyl halides, since the chlorine atom seems to leave in an almost SN1 fashion?  Wouldn't the carbocation formed be too unstable?  Also, by looking at the mechanism, it doesn't show anything displacing the Cl, or pulling it off the alkyl halide.  Would this reaction work for methyl-chloride (which would form a methyl cation)?  Just curious, the process seems to form a really unstable intermediate in some cases.

A little Orgo Humor

A helpful hint before the test! Don't just do the Sapling. Even after you complete an answer go look at the solution that sapling provides (the last tab at the top, once you get a correct check mark). It teaches you why your answer is right... (just in case you guessed or reached it by luck). Good luck on Friday's exam!

Quiz #5

I have a question about Quiz #5. The second question that entailed circling the compounds that are aromatic. Why is the third compound not aromatic? There are two double bonds in the cyclohexene ring, but there is also a pair of elctrons on another carbon. That acts as another pair and resonance is possible more than once. Why is it not aromatic?

I found two videos on aromatics, on youtube that I thought would be helpful and clear some things up.  Its basically what we went over in class, but they could be helpful as a review.

I hope this helps everyone in preparation for the quiz!!


http://www.youtube.com/watch?v=RaBI3lAACKg


http://www.youtube.com/watch?v=y7EcHL0V5ew

PGM

Can somebody explain this to me?

Hi All,

Can somebody explain to me why this compound (tetralin- C10H12) is aromatic (Sapling Q.4a) even though it has sp3 carbons in the second ring.

ACID CATALYZED DEHYDRATION OF 2-METHYL-2-BUTANOL

Hey guys so we did this synthesis experiment in lab and I wanted to share it with you:

An acid catalyzed dehydration of 2-methyl-2-butanol was performed to produce a mixture of isomeric alkenes: 2-Methyl-1-butene and 2-methyl-2-butene. The product was characterized by taking the IR spectrum of it, and the exact ratio of the each isomer present in the product was calculated form the NMR spectrum giving a percent ratio of 20% for the isomer  2-Methyl-1-butene and 80% for 2-methyl-2-butene which supports our prediction in which the dominant or major product would be the 2-methyl-2-butene because of its more conjugated alkene that is more stabilized that the primary alkene in the second (minor) product 2-Methyl-1-butene.

Using ChemDraw I did the mechanism of the reaction, and it's as follows:
 

The procedure of the experiment was adapted from:  K.L. Williamson, “Organic Experiments”, 9^th ed., Houghton Mifflin, 2004. 
Article on SciFinder pertaining to the reaction: https://scifinder.cas.org/scifinder/view/scifinder/scifinderExplore.jsf 

Sensitive Spectrophotometric Determination of Atenolol in Pharmaceutical Formulations Using Bromate-Bromide Mixture as an Eco-Friendly Brominating Agent

Researchers in India have developed a method for determining the presence of Atenolol in bulk drug and tablets.  Atenolol is a popular beta-blocker used world wide for the treatment of hypertension, heart failure, and cardiac arrhythmias.  It has other off label uses such as in the treatment of migraines, anxiety, or alcohol withdrawal.  (Interesting side note about about beta blockers; they are banned substances for athletes competing in sports such as archery, shooting, or golf as they are considered performance enhancing because they reduce the symptoms of sympathetic nervous system's fight or flight response.)  The authors of this study developed three new spectrophotometric methods for the analysis of atenolol based on bromination of atenolol by using an eco-friendly brominating agent.  The initial bromination step of atenolol is shown below:

Link to the study:
 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3335304/

Chapter 11 Sapling Homework

On number 8 in the sapling homework for chapter 11, I have some trouble finding the product of the reaction sequence. I have to find the product  from a cyclohexene adding PhCOOH, EtLi then H3O+, and PCC. It would be great if any of you can help me figure out this problem. I want to know how it forms the product.
 I have been having trouble with finding the product or the mechanism with like this problem. It would take me forever, so many tries, just to find an answer but I still not understand it. Is there any trick to  start to understand problem like this so it would be easier to do the problem? Or are there certain steps I need to do in order to get to the right answer? 

Excellent article.

http://www.slate.com/articles/health_and_science/medical_examiner/2013/02/curing_chemophobia_don_t_buy_the_alternative_medicine_in_the_boy_with_a.single.html#pagebreak_anchor_2

Friday seminar; Dr Prisinzano on Salvia Divinorum

I attended the seminar this Friday where Dr. Prisinzano from the University of Kansas gave a presentation on his research with the plant Salvia Divinorum.  The plant is known for its hallucinogenic properties when smoked and Dr. Prisinzano's work with the isolated psychoactive compounds has shown a lot of promise for medicinal uses.  He gave quite a few details on how the compounds can be manipulated through organic reactions and how the smallest changes can make a large difference in how effective it was.  In one instance he showed how the receptors for this compound preferred a certain stereochemistry at one of the asymmetric centers, and changing that made it much less effective.  He discussed how the compound was insoluble in water which is a problem that must be overcome for medicinal use.  
Of the many reactions he went over in manipulating the compound only a few were familiar to me with what we have covered so far in studying organic chemistry.  In one case a Diels-Alder reaction was used to add a ring to the compound.  A lot of what we learned this week with the Palladium catalyst Pd(PPh3)4 and Suzuki reactions were used in the synthesis reactions he went over.  
One of the biggest differences between this compound and opiates or other alkaloids was that it does not contain a basic Nitrogen in the compound; which was thought to be necessary to interact with opioid receptors.  This makes the compounds derived from the plant Salvia Divinorum unique and opens up a lot of new possibilities.  Dr. Prisinzano went into a lot of detail on research done with one derivative called Herkinorin which was experimented with on rats.  Herkinorin acts as an analgesic and the study showed that it does not have the same problems that other opiates have with tolerance.  The rats grew an extreme tolerance to morphine and was not effective unless the dose was increased.  The problem Dr. Prisinzano outlined is that you can only do this so much until it kills you, so there is a "ceiling" with the dosing.  Herkinorin did not seem to have the problems of tolerance that morphine had in the rats and implicates huge benefits in medicine.  This was one of the aspects Dr. Prisinzano focused on the most but it seems that research done on other derivatives could open up a lot more possibilities.  He also showed how over 60% of drugs since the early 1980's were derived from natural origins.  
This was the first seminar I have attended and I found it very interesting and plan on going to more this semester.  I would encourage anyone in our class to attend one of these if the topic interests you.

50+ Tries on Sapling Problems

Ok, so, it's been a couple of years since I've had Organic Chemistry I. I remember most of the stuff, but synthesis problems are my real weakness. I think when I have >50 tries on a sapling problem that's a pretty clear indicator that I don't understand what's going on. For every synthesis problem I make too many mistakes on, I'll post the full mechanism in the comments of this post (after the due date of course, I'm not going to do your homework for you.) The mechanism might be wrong, and if it is, please help me by pointing out my errors! Also, you guys should feel free to post your own mechanisms here too.


tl;dr: I'm going to post mechanisms to sapling problems in the comments, and you should too.