11Sep 2015 by Vincent Summers No Comments

Do Double Bonds Flip? Does Electron Density Move?

Chemistry
[caption id="attachment_7788" align="alignright" width="440"] 1,3,5 Hexatriene - NIST Image[/caption] How do double bonds flip, and what is the significance? The shorthand drawing of a double bond looks like an equal sign between two atoms. The double bond between the two carbon atoms of ethene gas, H₂C=CH₂, well illustrates this. Some organic compounds possess conjugated (alternating) double bonds. A simple example of this is 1,3,5-hexatriene. [caption id="attachment_7785" align="alignright" width="340"] Fig. 1. 1,3,5 Cyclohexatriene.[/caption] What If? But what if the ends of that 1,3,5 hexatriene are joined, with the loss of two hydrogen atoms, to make a ring one might be tempted to call 1,3,5-cyclohexatriene? In fact, such a molecule, if flipped left-to-right, is seen to be identical with 2,4,6-cyclohexatriene! The numbers can be dropped and the molecule can simply be named…
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23Mar 2014 by Vincent Summers No Comments

The Quintessential Aromatic Hydrocarbon Benzene (Pt.3)

Chemistry
[caption id="attachment_18860" align="alignright" width="440"] Figure 1.[/caption] The aromatic hydrocarbon benzene, chemical formula C6H6, is the single most-often discussed of the aromatic hydrocarbons. It possesses the quintessential aromatic structure. How is that? It possesses the Hückel Rule correct number of 4n + 2 number π-electrons, for n = 1, and is flat. In addition, it meets all the other requirements for aromatic compounds. As an aromatic compound, its chemistry is considerably different than it would be if it existed as a mere cyclohexatriene isomer. We will discuss those differences in this, the third installment of our three-part article. Behavior of Hypothetical Cyclohexatriene Since cyclohexatriene would behave as if it were merely three conjugated1 double bonds, we would expect the compound to behave as any other alkene—rich in available electrons—only more so.…
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