Sciencemadness Discussion Board

How can someone be successful in Organic Chemistry?

mustie - 19-10-2004 at 00:05

Hi everyone,
i need some advise..My area is Environmental Science, but i wanna study organic chemistry by myself..i took organic chemistry I & II in two semester when I was at the university. Unfortunately, I couldn't understand the spirit of organic chem. what can you suggest? the way? textbook?
thanks,

Magpie - 19-10-2004 at 08:11

Taking 2 semesters of organic chemistry is the right approach for learning the mechanics of this discipline. But I agree that the spirit must be right for you to truly thrive and enjoy it. That has to come from inside and cannot be taught in a school. I would suggest surrounding yourself with others you like and who do well in this subject. Hopefully their enthusiasm will rub off. ;)

mick - 19-10-2004 at 08:57

If you want to be an organic chemist I think you should learn about heterocylic chemistry.

mick

svm - 19-10-2004 at 12:42

this is my favorite textbook for organic chem:

http://www.oup.co.uk/best.textbooks/chemistry/clayden/

it explains lots of concepts from basic on to advanced. I find the explanations to be very clear compared to a lot of other organic texts. it's also has a lot of applications of the chemistry along the way. for example, when the book talks about the wittig reaction it gives an example of a pharmaceutical compound that was made with a wittig reaction.

JohnWW - 20-10-2004 at 15:28

You had better upload it to our FTP site, then, if it is that good.

vulture - 21-10-2004 at 01:42

Now, now John, pretty please usually works better. Besides don't everyone has the time and/or technique to scan books.

Something funny I noticed is that people who are exceptionally good at math have great difficulties with organic chemistry. I have no idea why though.

Organikum - 21-10-2004 at 01:58

Quote:

Something funny I noticed is that people who are exceptionally good at math have great difficulties with organic chemistry. I have no idea why though.

Maybe because organic chemistry is almost completely unlogical?

vulture - 21-10-2004 at 01:59

Hmm good point. I wouldn't say competely illogical, but contra intuitive often, no?

svm - 21-10-2004 at 08:08

yeah, sorry, no scanner here.

I think the math/organic chem divide might be because organic chem is very visual. it's more of a spatial relationship problem than anything else. not all mathematicians are used to thinking about things that way.

plus, you can theorize about what will work and what won't work for a particular reaction, but you'll never know until you actually try. in the reaction pot the problem becomes much more complex.

Magpie - 21-10-2004 at 09:38

Not only is organic chemistry spatial but the nomenclature and other memorization requirements are sizeable. I have to work harder in organic chem than other branches of chemistry that are more math based. Organic can be brought under control with logic - sort of. But only if you are really good at moving electrons around! ;)

Organikum - 22-10-2004 at 05:31

Except for the voluminous databases of reactions and basic schemes there is no difference between organic chemistry of today and the alchemy of the dark ages. Both use babylonic nomenclatura as disguise for the fact of "not-really-knowing-much" and both have no working theoretical backbone.


Organic chemistry is not able to answer simple questions like:
"Why does ClHO oxidise BzOH to BzCOOH but TCCA oxidises BzOH to Benzaldehyde? (TCCA is told to release ClHO on contact with water...)"

hehe.... ;)

svm - 22-10-2004 at 13:48

true, we can't explain a lot of specific reactivities, so there is still a lot we don't know. the methods of purification and structure identification are far better than anyone could have conceived in the dark ages.

vulture - 22-10-2004 at 14:16

What fun would it be knowing exactly how everything works? That would be a major blow to research. Not to mention how boring everything would be.

No, this is not a plea for religion.

Off-topic = on topic

Mephisto - 23-10-2004 at 02:56

Quote:
Originally posted by Organikum
Organic chemistry is not able to answer simple questions like:
"Why does ClHO oxidise BzOH to BzCOOH but TCCA oxidises BzOH to Benzaldehyde? (TCCA is told to release ClHO on contact with water...)"
Also the HOCl oxidizes BenzOH at first to the aldehyde as intermediate, but in the presence of water the reaction goes further to BenzCOOH.

In the reaction between TCCA and BenzOH, there are no water-molecules and therefore the reaction ends with the Benzaldehyde. (I think, the creation of cyanuric acid as a by-product catches any new formed water-molecules.)

There are analogue reactions of alcohols with PCC (Pyridiniumchlorochromate). Because of the evolving of pyridine instead of water (like in the case with H2SO4 and Na2Cr2O7) PCC oxidizes only to aldehydes.

Organikum - 23-10-2004 at 03:05

The reaction of TCCA and BzOH is done using a large excess of water.

Mephisto - 23-10-2004 at 03:21

But it was a nice theory... ;)

So I've got no idea what's the mechanism of this reaction, must be any black magic, as you said. Are there any references to this behaviour, or is it only empirical finding?

Organikum - 23-10-2004 at 04:02

Yes, of course this is referenced.

The TCCA reaction is:
"Direct Conversion of Ethers to Esters by Trichloroisocyanuric Acid"
Tetrahedron Letters No. 55, pp. 5819-5820, 1968

To find here


The HOCl reaction is common knowledge IMHO.



[Edited on 23-10-2004 by Organikum]

Mephisto - 23-10-2004 at 04:31

Quote:
Tetrahedron Letters No. 55, p. 5820
It is interesting that this reagent (i.e., trichloroisocyanuric acid), which generates esters from ethers will, under the same conditions, oxidize benzyl alcohol no further than benzaldehyde.
Which means, that the author has no clue, why this happens :P

Sociopath - 18-12-2004 at 11:47

Quote:
Originally posted by vultureSomething funny I noticed is that people who are exceptionally good at math have great difficulties with organic chemistry. I have no idea why though.


That is an interesting observation! I was discussing this with someone just the other day. It is indeed what I have observed as well.

Unfortunately I have had to attend the calculus at the univ and to me personally math seems like a total waste of time. And bearing in mind that I can't apply math to make anything with my hands that I will find interesting makes it extreamly hard to study, since I'm constantly reminded that I'm wasting my time. This is not true for organic chemistry. You can sit with a matrh-problem for several hours and when you have solved it you feel empty, since there is another problem waiting when you turn the page and it will also take severel hours to solve and you have still gained nothing, it is some real stupidity and I will never understand the point of it. It came as no surprise to find out that the inventor of the integral calculus Isaac Newton lived his entire life in celibate...

Thomas Winwood - 18-12-2004 at 12:11

Newton rediscovered differential calculus. Integration wasn't known to be connected until a good while afterwards.

(Differentiation was discovered by Pythagoras anyway. :p)

Geomancer - 18-12-2004 at 17:53

Thomas Winwood: I don't think so. Not only did the Pythagoreans not posses any analytic knowledge, thier whole mindset was profoundly anti-analytic. They had great problems with the notion of a continuous number system, and in the end had to largely separate geometry and arithmetic.

Archimedes did do some analytic type work. His methods foreshadowed integral calculus.

Newton and Leibnitz were well aware that integration and differentiation are inverse operations.

Formal understanding of analytic operations had to wait several centuries, though.

Thomas Winwood - 18-12-2004 at 18:02

You're right, it was Archimedes who first discovered calculus.

alchemie - 18-12-2004 at 18:16

Quote:
Originally posted by Organikum
Except for the voluminous databases of reactions and basic schemes there is no difference between organic chemistry of today and the alchemy of the dark ages. Both use babylonic nomenclatura as disguise for the fact of "not-really-knowing-much" and both have no working theoretical backbone.



That is not quite right.
Although most of the reactions used routenily by synthetic organic chemists do not habe a theoretical support there have been great advances in theoretical organic chemistry in the last decades. Mainly connected to the development of more eficient quantum chemistry methods and faster computers.

What happens is that, in most cases, it suffices that the reactions work, and little knowlege of how they work is needed for application in the pharmaceutical or whatever industries, as long as they can be made to turn a profit.

Thats what spawns the massive reaction databases. The need for a zillion methods, optimized by trial and error, ready to apply to the industrial scale.


Fo these reasons the effort associated with the practical aspects of organic chemistry is much more than the theoretical ones and this situation is not going to change in the near future, at least until the predictive power of computational chemistry is greatly increased, and the computation times greatly diminished.


Apart from these considerations I really enjoy the artistic part of synthetic organic chemistry.

Quantum - 12-3-2005 at 15:35

Yep we are still in the dark ages as to why things happen - but look at all the stuff we have made

[QUOTE]this is my favorite textbook for organic chem:

http://www.oup.co.uk/best.textbooks/chemistry/clayden/

it explains lots of concepts from basic on to advanced. I find the explanations to be very clear compared to a lot of other organic texts. it's also has a lot of applications of the chemistry along the way. for example, when the book talks about the wittig reaction it gives an example of a pharmaceutical compound that was made with a wittig reaction.[/QUOTE]

I just ordered that book from Amazon an hour ago - hopefully it will be good and I will learn organic chemistry. The sample chapters looked good and you can read them from that website as PDFs

Sandmeyer - 11-5-2005 at 10:37

i stumbeled on a pretty interesting article:

http://www.iupac.org/publications/cei/vol4/0401x0an1.html
[...]

CEI: You mean that you began doing experiments by yourself? In your room, or...?

JML: My parents lived in the countryside in this small town, so I did the experiments in the courtyard. I started doing experiments using the 'Gatterman'(2)- you know this German preparative chemistry book? - to learn to do distillation, to synthesize indole and other compounds.


CEI: That's fantastic. Without any private tuition?

JML: Without any private tuition. I had a good friend who was also very interested in that, and so we bought chemicals and glassware. During my first year at university, when it is very general, we did a lot of experiments at home.


[...]

Nicodem - 11-5-2005 at 13:48

In science we use theories in order to avoid using magic.
A theory is an explanation based on arguments that has to always be considered a not-the-full-truth, but just a useful-wannabe-truth. A theory must be always applicable. If it is not, then it is bad theory that needs updating.
Magic is wishful thinking that might or might not work.

For example, from Organikum’s exemplary problem of benzylalcohol oxidation I wrote a simple theory that explains why the reaction works as it works with TCICA and hypochlorite:

Unfortunately it is better shown in a graphic than it would be in words. That’s the beuty of organic chemistry.


___________________________________
PS: I hate mathematics, especially calculus.