5 - Chapter 5 The diversity of organic structures The...

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1 Chapter 5 –The diversity of organic structures The functional groups of organic chemistry We began our study of organic chemistry with an organizational chart of the electron configurations of H, C, N, O, and F. We called this the “Building Blocks of Organic Chemistry”. Now we are ready for the next level of structure – the organic functional groups. Functional groups are the common ways that the building blocks come together. We want to compile a list of all the functional groups that we will encounter in this course. Just as was the case with the building blocks, we provide a complete list now, so that you will recognize the structure of the functional groups the first time you see them in the text. A list of organic functional groups is compiled as an appendix at the end of this chapter. Please look at these functional groups now. Can you see that each functional group is constructed from combinations of the building blocks? If we wanted to be hyper systematic, we might consider constructing a table in which all the building blocks are placed across the top row and down the left-hand column. This is like a matrix. The intersection of a column and row is a building block combination and potentially a functional group. In reality, this imaginary table is a little impractical, so we’ll just stick to our list. In order to speak the language of organic chemistry, the common functional groups have to be memorized. As you memorize these groups, take the opportunity to practice your skills with the building blocks (e.g., always add the proper number of electron lone pairs on each heteroatom; always assign formal charges). The Universe of Organic Molecules The same functional group in different molecules exhibits similar properties
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2 With this introduction to functional groups, we are now ready to consider the next stage of organic structure – molecules. You see from the example above that, just as the building blocks combine to make functional groups, the functional groups come together to make molecules. In this way, complex organic molecules like prostacyclin can be thought of in terms of rather simple pieces. Most of the functional groups in prostacyclin are isolated from one another. That is, they are separated by alkane building blocks. Isolated functional groups are expected to behave the same from one molecule to the next. For example, the carboxylic acid in prostacyclin is probably going to behave the same as a carboxylic acid behaves in any other molecule. Notice however, that there is a pair of functional groups in prostacyclin that are not separated. In particular, notice that the ether group overlaps with an alkene. This combination of adjacent functional groups gives rise to special behavior, as we will shortly see. But let’s not worry about that for now. For now, all I want is for you to develop the skill of recognizing the various functional groups, whether separated or combined.
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This note was uploaded on 10/02/2008 for the course CHEM 232 taught by Professor Vanderdonk during the Fall '08 term at University of Illinois at Urbana–Champaign.

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5 - Chapter 5 The diversity of organic structures The...

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