10Aug 2019 by Vincent Summers 1 Comment

Organic Ozonides – How They Form, How They React

Chemistry
As you might guess, organic ozonides may be derived from ozone. So let's first consider the nature of ozone. The ozone molecule, O3 is bent and unstable. It is polarized and is quick to react with unsaturated molecules, notably alkenes and alkynes. The image provided illustrates the result. What, however, is the mechanism producing the result in a typical case?¹ Initially, all three oxygen molecules add to the alkene on the same side of what was previously a double bond. This structure, however, is a transient intermediate, which rearranges to form the ozonide structure. Ozonides are relatively stable. However, they can be readily split to yield a pair of carbonyl compounds. Organic Ozonides in Synthesis Some ozonides are explosive, so they are seldom isolated. However, ozonides can be made to…
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11Apr 2016 by Vincent Summers 10 Comments

Vanilla and Vanillin: What’s the Difference?

Chemistry, Food
[caption id="attachment_14041" align="alignright" width="440"] Drying vanilla beans.[/caption] Probably the average grocery shopper is unaware there are two sources of the flavor of vanilla. They are vanilla and vanillin. Are they the same? Are they different? If they are different, what is that difference? Vanilla and Vanillin Historically, our favorite ice cream flavor has been vanilla. To draw special attention to the use of natural rather than synthetic ingredients, some have added descriptors to their ice cream. They use phrases like natural vanilla or natural vanilla bean. The vanilla bean comes from an orchid, and is completely natural. The flavor extract made from it is called vanilla. Yes, the word that ends in an “a,” and not an “n.” We still have vanilla and vanillin. So what is vanillin? [caption id="attachment_17377"…
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17Nov 2014 by Vincent Summers No Comments

Keto Enol Tautomerism

Chemistry
Is the term keto enol tautomerism familiar to you? If not, give attention to the ensuing discussion. Organic chemistry would be of no value if not for multiple bonds and functional groups.  Such groups impart the reactivity needed to sustain life. One attachment is carbonyl (–C=O). Tautomerism Given the right environment, atoms of a carbonyl group tautomerize. That is, they can exchange a proton (hydrogen). In so doing a π-bond is formed or disappears. The carbonyl or keto form assumes the alkene-alcohol or enol form, or vice versa. For acetone, the two forms are, CH3–(C=O)–CH3 keto form CH2=C(OH)–CH3 enol form See the image above. [sc name="MidArticleAdsense"] Both Aldehydes and Ketones Participate A ketone has its carbonyl carbon atom linked to two other carbon atoms. An aldehyde has its carbonyl carbon…
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