New Release: Unit 14 Nomenclature Part B & Unit 15 Conjugation and Aromaticity are now available for purchase through the site. You can purchase the Semester 1 book for $40 at the Organic Chemistry Stores (W1-22) of the University of Alberta.

The 2 Essential Oxidative Bond Cleavages to Form Carbonyl Compounds

Learn the key oxidative cleavages to form carbonyl compounds, from ketones to carboxylic acids, in organic chemistry. Visit Unit 8 for more.

In these reactions we totally break (i.e. cleave) a C-C double bond and replace it with two C-O double bonds to form various types of carbonyl compounds.  Depending on how harsh the oxidation is, you get different types of carbonyls.  The meaning of oxidation states in organic chemistry is discussed in 8.3. This is very different than what you learned in general chemistry.  Carbonyl reactions are the most important  type of chemistry you will learn in semester 2.

8. Most Highly Oxidized Products: Harsh Reagents (8.3B)

Hot KMnO4 is a very harsh oxidant and when it blows apart the C-C double bond, it can yield a  carboxylic acids if the alkene carbon has 1 or 2 H’s on it. Carboxylic acids  are the most oxidized carbonyls (i.e. have the most possible bonds to oxygen). In this reaction or 9 (below),  if your alkene carbon has 2 alkyl groups on it, it will always be converted to a ketone regardless of harsh or mild conditions.

9. Less Highly Oxidized Products: Mild Reagents (8.3C)

Ozone with a zinc/acetic acid workup in step 2 is a more mild oxidant.  When it breaks the C-C double bond, the result is less oxidized aldehydes instead of the carboxylic acid you would get in reaction 8.

If you want to learn more about these reactions so you can remember them better or if you want to try some good practice problems go to Unit 8 and the particular sections indicated. 

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Dr. B Tips

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