Organic Chemistry

I'm trying to figure out shorthand ways, ways to write down things faster. So, I recently learned that instead of writing C=O, I can just write CO. For instance... I know that for benzene, a person can draw a six-carbon ring and put in a circle. What about the image I uploaded? Can I put a ring in there instead of drawing the three lines? Imagine I had to draw this thing like 20+ more times... I'm looking for shorthand ways of drawing these things out.

Hey Everyone, Anyone out there have any idea on the mechanism for reacting 2,2-dimethylcyclohexanone with H2SO4 to yield 2,3-dimethylphenol. Once you protonate the ketone and form a benzene ring, how the heck is the methyl moved down to the 3 position?

peace be upon you all What's the differenece between mesomeric and inductive effect? and please mention the famous groups and if it produce mesomeric or inductive effect also if they are electron donating or electron withdrawing groups thanks very much I wish you are fine

Hey guys, I'm having trouble drawing all the trans isomers of dichlorohexane (in chair form) can someone please tell me how many there are and possibly draw them for me. Thanks!!

which effect is stronger if both are competing : mesomeric or hyperconjucation due to alpha hydrogen?? pl help!!!!!

I have no idea about the mechanism of this reaction. Anybody could help? Since according to wikipedia, TiCl4 is a Lewis, acid, we could propose this mechanism: One drawback is, that i would not see how we get rid of the Titanium lewis-acid in the last step to furnish a reduced product. (Reductive workup perhaps?) The second thing is that wikipedia states, that TiCl4 is an oxophiliic lewis acid. So, coordination to the oxygen in the first step in order to activate the carbon... The problem is, that lewsi activation of vinly ethers activate the carbon beta to the ether oxygen and the thiol would attack at the wrong carbon. Plus, we need double activation t…

Its easy to forget the humble TLC when faced with todays analytical equipment (LC-MS, GC-MS, etc). To this end, I though it would be useful for people to have access to the range of stains that you can use on TLC to reveal a whole range of functional groups. Even now, doing a PhD in a department with plenty of analytical machines, TLC is still usually my first port of call when analysing a reaction mixture. http://pcwww.liv.ac.uk/~jxiao/TLC%20Stain.pdf

Hi everyone can anyone tell me what are the cheapes polyesters and hydrogels?? Thanks in advance

The reaction is 5-bromo-butanol with Sodium Hydroxide (NaOH) would give you a cyclic ether. I understand the mechanism but I would like an explanation why the base (OH) picks up the H on the alcohol (OH) instead of a back side attack on the carbon with the bromine. Would appreciate the help, thanks!

To get large rings (with a endo lactone functionality) closed, the traditional approach has been to use macrolactonization. Because the entropy factor overrides the enthalpy factor for large rings, suppression of the intermolecular reaction becomes more difficult. That problem was addressed by activation of the carboxylic or alcohol moiety, for example by the use of thioesters to "push" the reaction against entropy by increasing the enthalpy (correct my, if i am wrong here). in the last time, i came over an immense number of examples where rings were closed by ring-closing metathesis (thanks be to grubbs). is the time of macrolactinzation finally over? opinions, ple…

Okay... Stereochemistry has never been my strong point, so seeing all of this chiral stuff in the carbohydrates chapter is kind of freaking me out. My book is confusing the heck out of me. Is there any trick to figuring out optically active carbons in a carbohydrate ring? Only 4 problems left, BTW... Out of 80 problems covering 8 chapters, 3 of which I haven't even done yet. The chirality is a multiple guess problem, so if worst comes to worst, I'll just... guess. I've got 3 "guess the product/intermediate" problems left but I don't have it in me to try them tonight. Tomorrow is another day! I'm going to bed.

Hello again! I'm back with another Orgo 2 question. My prof has set up some online homework questions that require a registration code that came in the shrink wrap of the textbook. Not knowing that I'd need to keep the stupid shrink wrap, I tossed it and am forced to do a whole semester's worth of homework in 4 days as I'm on a "free trial". That being said, I might have a bunch of questions between now and the weekend. I've done 4 chapter's worth of the homework so far, but I'm stuck on the last problem of the 5th chapter. Haven't even looked at the other chapters yet. *mutter* So here's my question... First off, I'm not 100% sure of the name of the starting c…

Here's another one... =) An unknown amino acid was treated with ninhydrin in -OH/H2O. On completion of the reaction, a compound that gave a positive Tollens test was isolated from the product mixture. Its 1H NMR spectrum exhibited resonances at 1.10 (d, 6H), 2.20-2.60 (multiplet, 1H), 9.60 (d, 1H) ppm, and three distinct signals were present in its 13C NMR spectrum. Draw the structure for the unknown amino acid. Do not draw the zwitterionic form. Now, I drew 2-amino-2-methylpropanoic acid as the unknown. I figured that would give 2-methylpropanal when treated with ninhydrin. That would give a positive Tollens test, three 13C NMR signals, and the appropriate …

hi friends, i have seen a good website for organic chemistry video lectures.in that website you can watch 100's of videos and you can download all videos in flv,3gp,mp4 formats. here is the link organic chemistry video lectures

Beare, N. A.; Hartwig, J. F., J. Org. Chem. 2002, 67, 541. Well, inspired by the methodology from the paper above, I tried to make a palladium-catalyzed intramolecular cyclization on a substrate like this: When I use KOtBu as the base, nearly half of the product is the hydrodehalogenated one (the one below). Cyclization occurs quantitative, though and without side-products, when I use NaOtBu. I totally do not understand that. The solvent is toluene. Na3PO4 does not work at all and K3PO4 works as good as KOtBu. Can anybody explain these strange results? Thanks, Dan

Hello all, I need to be able to write a complete mechanism for the oxidation of cyclohexanol, specifically using sodium dichromate dihydrate, and acetic acid. The problem is we were never given a complete mechanism in class so all I have are educated guesses. I wasn't able to find this particular reaction online(i found some with acetic acid, and some with Na2Cr2O7, but none with both) I'm pretty sure that the acetic acid protonate the oxidizing agent, and I'm sure it attatches to the ring and is then pulled off, but i'm not sure of the particulars. I also wanted to know what was the most widely accepted mechanism for the reduction of cyclohexanone using NaBH4

would any one know the chemical compersistion of the sap of the pachypodium genus? they are used as arrow poisons so they must be quite potent. i have a hunch that the toxins are alkoids and ae related to the oleandrin glycoside alkoids that are found in the plant oleander, which is a cardiac toxin. the reason behind this is that if you google it there is no infomation upon the topic! the only reason is the need to know:P

A lot of my synthetic routes at the moment require me to oxidise alcohols to aldehydes. Until recently, I have been using the Swern oxidation; while this has been working perfectly well, its just too fiddley keep everything at -78OC and anhydrous as well. I have since found the great hypervalent iodine oxidant 2-iodoxybenzoic acid (IBX); an older version the the Dess-Martin periodate. http://pubs.acs.org/doi/abs/10.1021/ol026427n This reagent is unfazed by air or moisture and is basically insoluble in almost all organic solvents. While this might sound pretty useless, as elevated temperatures, enough is soluble to make this reaction efficient. At the end of …

Hi all, since I have a lot of questions about what is commonly referred to as "Total Synthesis of Natural Products", this Topic is for questions about it that might occur to anybody at any stage of their organic synthesis efforts. My first question would be this: Why is the first synthetic aproach towards a target molecule always a racemic approach using racemates as starting materials? Is it not possible that the diastereomers, thus formed, will react quite differently giving misleading results and yields? Thanks to everybody in advance for their help, answers and questions. Dan

I'm reading my organic chem. book as a supplement to lectures, and I came across an oddball aspect of mixed claisen condensations. Supposedly, there is the trend that an alpha-carbon attached to the other carbonyl carbon of the other ester. Ok, but how is that working for diethyl carbonate? It doesn't seem to have an alpha-carbon or alpha-protons. How does this work out? I'm guessing if I could see the mechanism, I could make sense of it; but there is no mechanism for that particular compound. I'm guessing that the oxygen acts like carbon for the mechanism? As such, the oxygen, similar to the alpha-carbon's position, attaches to the carbonyl carbon of the oth…

Hi! I'm new here (will introduce myself shortly!) I'm in Organic Chemistry 2 and have a problem that no amount of pondering or doodling is helping me solve. Here's the problem... Below are the 1H and 13C NMR spectra of a dichloroalkane. Analyze the spectra and propose a structure consistent with the data. Provide a COGENT explanation outlining how you arrived at the proposed structure. The 1H NMR isn't super clear, but it looks like there's a sextet between 4.5 and 4 ppm (small... maybe 1 H), a triplet between 4 and 3.5 ppm (maybe 3 H?), a quartet between about 2.3 and 2 ppm (maybe 2 H?), and a doublet around 1.5 ppm (tall... Maybe 6H). The 13C NMR i…

I figured I would start a thread for us chemistry folks to post some reaction schemes and discuss synthesis design, as well as relevant laboratory techniques. I'll start things off with the total synthesis of Sildenafil [trade name "Viagra"]. The drug is administered orally as the ammonium-citrate salt. This is the lab scale synthesis and is covered in detail in Bioinorganic and Medicinal Chemistry Letters Vol. 6. This scheme is brought to you courtesy of: www.ch.ic.ac.uk Notice the sulfonamide that shows up in the last step. I chose this synthesis because of the simple functional group transformations that lead to a highly marketable drug. I als…

So for tlc, in selecting the correct mobile phase and stationary phase what are the factors which influence what ones you choose, how do you decide what ones to use?

I was reading about various halogenations with acetone (Br, I, and Cl). However, does fluorine have the same reaction rate with acetone during halogenation? Yes? No? If not, why so?

might one of you guys please tell me what is the theoretical background of the mixed solvents recrystallization ?