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Hi everybody–
It’s been over two years now that we have been giving you our organic chemistry tips, now it’s your turn. Tell us what trick your profs tried to pull on you, or a slick way around a problem that you might have seen. We will take the best ones and use them in a future post.
Hi Everybody, browsing again I found that AceOrganicChem.com has recently released review videos for organic chemistry that cover your entire semester. The videos are about 6 hours long, easy-to-understand, and only $8.99. I think that they not only useful for the end of the semester, but a nice review as you go along too. You can jump from topic to topic, go at your pace, and learn all of the tricks your professors won’t tell you. These get 5 stars from us here at this blog. Here is the link for the videos: organic chemistry videos, they are available to download immediately after your purchase.
Good luck and happy reacting
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Don't be so hard on yourselves.
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Let’s face facts: alkanes don’t have many uses. In real life, they are non-polar solvents, larger-chaines ones can be used to make wax, and they are good for burning/they make good fuels. As far as organic chemistry goes, alkanes are very boring. They have only three uses in your class:
1) Solvents: Alkanes are very good non-polar solvents. See tip #XX for more information on this.
2) Halogenation: Alkanes can be reacted with bromine or chlorine under free-radical conditions to obtain an alkyl halide. See tip #XX for more information on this.
3) Combustion: This is the fuel part. Complete combustion is an alkane reaction with oxygen to obtain CO2 and water, as shown in the following example: C3H8 +5O2 à 3CO2 + 4H2O + Heat
There is only a small possibility that you will see a combustion reaction on one of your exams. Therefore, the only real uses for alkanes in your undergraduate organic chemistry class will be as a solvent or in a halogenation reaction. Hence, if you have an alkane in one of your exam reactions, it should be very simple to determine its role. If there is a halogen (usually either Br2 or Cl2) , then beware of a halogenation reaction. Otherwise, it is most likely safe to say that if you have an alkane in your reaction, it is a solvent and does not participate as a reactant.
For more helpful organic chemistry information, please go to organic chemistry.
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This is important throughout organic chemistry, but will be especially important when trying to determine the products of elimination and substitution (E1, E2, SN1, SN2)reactions. There are generally three trends to remember when discussing how nucleophilic a reactant is:
1) Size - Generally, the more linear and/or smaller the nucleophile, the more nucleophilic it will be. This is because it can react at more sites and will not be sterically hindered if it is smaller or linear.
2) Electronegativity- The more electronegative an atom is, the less nucleophilic it will be. This is because more electronegative atoms will hold electron density closer, and therefore will be less likely to let that electron density participate in a reaction. We see this in calculations and experiments that show nucleophilicity decreases as you get closer to fluorine on the periodic table (C > N > O > F)
3) Polarizability- The more polarizable an atom is, the more nucleophilic it will be. Polarizability is defined as the ability to distort the electron cloud of an atom, which allows it interact with a reaction site more easily. Generally, polarizability increases as you travel down a column of the periodic table (I > Br > Cl > F)
Below is a table of relative nucleophilic strength. This is relative because nucleophilic strength is also dependant on other factors in the reaction, such as solvent.
|
VERY Good nucleophiles |
HS-, I-, RS- |
|
Good nucleophiles |
Br-, HO-, RO-, CN-, N3- |
|
Fair nucleophiles |
NH3, Cl-, F-, RCO2- |
|
Weak nucleophiles |
H2O, ROH |
|
VERY weak nucleophiles |
RCO2H |
As shown above, as a general rule, the anion of a reactant will be a better nucleophile than the neutral form. (i.e. RCO2- is a better nucleophile than RCO2H)
For more information on this and other topics of organic chemistry interest, please visit organic chemistry
A problem we see students constantly running into is that they do not readily recognize strong acids. This is a terrible mistake and should never happen. You will need to quickly recognize strong acids and which atom they will be protonating. As far as strong acids go, you should immediately recognize the Magnificent Seven:
STRONG ACIDS: HI, HCl, HBr, HNO3, H2SO4, HClO3, H3PO4
Just think that that it’s the three hydrogen halides and the four acids that have N, S, Cl, and P as central atoms. Many students remember the other four acids with the mnemonic, something you would never say to a girlfriend: “Never Say ‘Please Clean’ ”.
Once you have recognized that you have a strong acid present in your reaction, it is necessary to determine what it is protonating. Remember that H+ is electron-deficient (Lewis acidic) and will look for an electron-rich (Lewis basic) atom to protonate. This could be a nitrogen atom, such as an amine, or an oxygen atom in a carbonyl or an alcohol. Most often, the atom being protonated will have a lone pair somewhere.
Take Home Message: Know the strong acids, the mnemonic Never Say ‘Please Clean’ might help
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Good luck and, as always, happy reacting.
