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Ch 12: Organic Compounds Containing Oxygen and Sulfur

The Big Idea: Functional Groups

Functional Group Name

Condensed Structure

Ending of Name*

Alcohol

R – OH

– ol

Aldehyde

R – C=O  – H

– al

Ketone

R – C=O  – R

– one

Ether

R – O – R

– ether      (R, R – ether)

Carboxylic acid

R – C=O   – OH

– oic acid  (R – oic acid)

Ester

R – C=O   – O – R

– ate          (R, R – ate)

Amine

R – NH2

– amine     (R – amine)

Amide

R – C=O  – N – R

– amide     (R – amide)

Thiol

R – SH

– thiol        (R – thiol)

Aromatic (Benzene)

R – benzene ring

– benzene (R – benzene)

Phenol (Benzene-OH)

Benzene – OH

– phenol)   (R – phenol)

Toluene

Benzene – CH3

– toluene   (R – toluene)

* R = the rest of the molecule

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Chiral Molecules:

Certain molecules do exist in two forms which are symmetrical mirror images of each other: they are known as chiral molecules. On Earth, the chiral molecules of life, especially amino acids and sugars, exist in only one form, either left-handed or right-handed. Why is it that life has initially chosen one form over the other?

http://www.sciencedaily.com/releases/2011/01/110107145634.htm

Left-handed and right-handed molecules can have completely different properties.  A consequence of the different properties in biological systems is that a molecule can behave either as Dr Jekyll or Mr Hyde. The different characteristics in the enantiomers can be harmless, like in the limonene molecule. One enantiomer smells like orange and the other like lemon.

Thalidomide is a good example of how different forms of the same molecule can have disastrous consequences. One of the enantiomers was calming and eased nausea in pregnant women, while the other caused serious damage to the fetus. The thalidomide catastrophe is one of the reasons that a lot of research is devoted to chirality, as it is absolutely vital to be able to control which form of the molecule that is produced. Research on chirality has resulted in several Nobel Prizes over the years.

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Chirality: New Method to Consistently Make Left-Handed or Right-Handed Molecules

ScienceDaily (June 14, 2011) — Many organic molecules are non-superimposable with their mirror image. The two forms of such a molecule are called enantiomers and can have different properties in biological systems. The problem is to control which enantiomer you want to produce — a problem that has proved to be important in the pharmaceutical industry. Researchers at the University of Gothenburg have now come up with a new method to control the process.

http://www.sciencedaily.com/releases/2011/06/110614122202.htm