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Question:How can I determine the reagents and conditions needed to form a particular product? Or what product forms when certain reagents in certain conditions react? Is there an extremely general and basic property/rules that will work for all kinds of organic chemistry reactions? I.e. is it like...determining which of the functional groups are acidic and basic, then knowing which gets protonated in either acid/base reactions. and like how a product will look based on each atom's electronegativity? Does anyone have a brief short summary of the fundamental mechanisms of most (if not all) organic chem reactions? Note: I know i need to memorize a lot of the reagents and types of reactions, but I want to know the most fundamental mechanisms. not just halogenation of an alkene = this and that. thanks!

Answers:You might consider my book, A Guide to Organic Chemistry Mechanisms. I wrote it by trying to emphasize the commonality of classes of reactions. You will recognize reaction themes on each page of examples. The best way to learn more about the book is to download and print out the minisampler. http://www.curvedarrowpress.com/agocm/inside/sampler/sampler.html You will be able to do all of the problems in Part A. The problems are repeated in Parts B, C, and D, what is learned in Part A, is repeated in the other parts. Part C is like the problems in a textbook and Part D is a completed mechanism.

Question:I just had a test on organic chem, and I don't know the answer to one of the questions. One question asked how one could form a cyclopantanone from a 1-bromo pentane aldehyde. a lot of people said to use grignard reagents, but i thought that would just lead to an ether, not a ketone. i said to use polar protic solvent, like an e1 reaction. then one end would be a carbocation; the other end could "curve over", forming a cyclic ketone.....although that doesn't sound too right. could anyone tell me with certainty how this reaction is supposed to go? is there any logic at all for what I wrote? (i'm still wishing for part marks if i got the question wrong).

Answers:The only flaw with your reasoning is that the carbocation formed by the E1/Sn1 reaction of a 1-Bromopentane Aldehyde would be so unstable that it will actually never form. The correct answer is, indeed, a Grignard Reagent. Sorry to be honest, but it's best if you learn this right now so when you take Org. Chem. II you're fine off. You should get some points, though, because your answer is not completely wrong or illogical. It's just flawed by the energy of the reaction.

Question:i'm having a tough time with these two questions squalene, first isolated from shark oil and a biological precursor of cholesterol, is a long chain aliphatic alkene C30H50. The compound undergoes catalytic hydrogenation to yield an alkane of molecular formula C30H62. How many double bonds does a molecule of squalene have? and give the names of five alkenes having the molecular formula C6H12 that produce hexane on catalytic hydrogenation

Answers:First off, just do simple subtraction from C30H62 to C30H50 to find out how many hydrogen atoms must have been added. You'll find that there were 12 hydrogen atoms added to squalene to get the alkane chain. If each double bond can acquire 2 hydrogen atoms (one for the adjacent carbon bond and one for the carbocation that forms when you break the double bond), simple division will yield that there were 6 double bonds present in squalene (12 H+ atoms / 2 possible H+ bonds to form = 6 double bonds). Now that you know how this worked, I'll leave you to finish the next question. You've gotta learn some way, right?

Question:I have more questions concerning your answer to a user about the mechanism of Cyclopentene + Br2 (link: http://answers.yahoo.com/question/index?qid=20080920153523AAMXYzG) I have further problems that similar. here is the page that has the problem: http://img60.imageshack.us/img60/5148/ochemab4.png I am confused of what to fill in for the two empty squares for each problem, can you help me? Thanks I'm also confused with these problems, if you have time please proceed to further explain how to solve these: http://img530.imageshack.us/img530/7720/ochem4and5we0.png Any help is welcomed.

Answers:The names are (1R,2R)-1,2-dibromocyclopentane and the S,S. The reaction (drawn for cyclohexene) is here: http://orgo.curvedarrow.com/punbb/viewtopic.php?id=168 The chlorination gives (1S,2S)-1,2-dichloro-1-methylcyclohexane and the R,R isomer. The bromination gives (1R) and (1S)-1-bromo-1-(bromomethyl)-2-methylcyclohexane. This name is a little truncated as the absolute stereochemistry of the methyl group is not specified and thus an additional set of names/products are present, though not specified. 4. This is essentially the same reaction as bromination with the following exception, because methanol (or water) is more basic than bromide, it is the better nucleophile and opens the bromonium ion intermediate. Again, there are two chirality centers so a mixture will result. 5. 1-bromo-1-propylcyclohexane. I am not going to draw the mechanism of this addition unless you need it. These questions are not difficult. Naming them should be the harder part of this exercise. However, this analysis is based upon knowing the reaction mechanisms. If you do not know the reaction mechanisms, I cannot encourage you strongly enough that it is on your interest to learn them, whether formally required in your class or not. If you do not know the mechanisms, I suggest you purchase the book, "A Guide to Organic Chemistry Mechanisms " available at Amazon.com, Barnes and Noble or http://www.curvedarrowpress.com . If you are concerned that you would have difficulty in learning the mechanisms, I suggest you could buy it from Curved Arrow Press directly. Their 10 day money back guarantee on the book applies whether you write in the book (it is a workbook) or not. However, you will find the mechanisms in "A Guide to Organic Chemistry Mechanisms" are very easy for you to understand. They logically connect all of the steps leading to the product.

From Youtube

Organic Chemistry EC :By Laurie Siu. For Professor Neil Garg of Chem 14D, UCLA. Original Song: Us by Regina Spektor. SORRY THAT I CAN'T SING! Lyrics: Intro: This is a story of nucleophile meets electrophile The nucleophile, compelled to donate a pair of electrons The electrophile, compelled to accept a pair. Neil drew a reaction on the board And made a clicker quiz for us. Now we know how to do a SN2 The nuc attacks the E And the leaving group just leaves, just leaves An inversion also takes place. 'Cause there was a backside attack This is a SN2. what UCLA makes us do. But don't forget about SN1. Dissociation, water attacks, and deprotonation. This is where A carbocation intermediate forms But there's also some competition under basic conditions Thru elimination Alkene formation E1 has weak bases And E2 has strong bases Then Chem 14d had their midterm 2 with alcohol and ether synthesis which includes epoxides too under basic and acidic conditions Alkene reactions had a lot of additions with conditions. Make sure to memorize all the reagents All of these same alkene additons can also be done with alkynes too Along with hydration And catalytic hydrogenation Alkenes and epoxidation dihydroxylation and ozonolysis Look out for Markovnikov and anti or syn Diels alder forms a cyclohexene and rxns with benzene use EAS Consider all that we have learned see how it works with carbonyls He'll mix these up and synthesize we must Know indigo and Sarain A 'Cause you might use it on final's day Plus extra ...

Organic chemistry: R and S naming (12) :Organic chemistry nomenclature: How to determine whether a stereocenter has R or S stereochemistry--ie, how to name the "absolute configuration" of a stereocenter. These videos are offered on a "pay what you like" basis. You can pay for the use of the videos at my website: www.freelance-teacher.com For a printable document containing the systematic method discussed in this video series, go to my website. For a list of all the available video series, arranged in suggested viewing order, go to my website. These videos are designed to help students who are finding the material difficult, so I go very slowly, with lots of repetition and examples. If you don't find this material difficult, you might be very bored by these videos and might prefer to learn straight from a textbook. For a playlist containing all the videos in this series, click here: www.youtube.com (1) How to determine priorities (2) How to determine priorities (3) How to determine priorities (4) How to determine priorities (5) Case 1: Priority 4 pointing into the page (6) Case 1: Priority 4 pointing into the page (7) The single-swap rule (8) Case 2: Priority 4 pointing out of the page or in the plane of the page (9) Case 2: Priority 4 pointing out of the page or in the plane of the page (10) Case 2: Priority 4 pointing out of the page or in the plane of the page (11) Case 2: Priority 4 pointing out of the page or in the plane of the page (12) Multiple stereocenters (13) Multiple stereocenters (14) Harder ...