Cleavage of Carbon-Carbon Bonds With Periodic Acid

The video tutorial by Professor Dave explains the importance of forming and cleaving carbon-carbon bonds in organic synthesis. It introduces Periodic acid as a reagent that acts as an oxidizing agent, particularly useful for oxidizing polyhydroxy compounds like vicinal diols. The tutorial provides examples with glycerol and glyceraldehyde, demonstrating how Periodic acid cleaves carbon-carbon bonds to form carbonyls. The mechanism involves the formation of a cyclic periodate ester, leading to the cleavage of bonds and formation of iodic acid and water. This technique is valuable for breaking molecules into fragments or converting cyclic substrates to linear ones.

Why is forming and breaking carbon-carbon bonds crucial in organic synthesis?

• To alter the color of organic molecules

• To assemble and isolate specific molecular fragments

• To change the state of matter of compounds

• To increase the molecular weight of compounds

What role does Periodic acid play in organic reactions?

• It serves as a reducing agent

• It acts as a Bronsted-Lowry acid

• It functions as an oxidizing agent

• It acts as a catalyst

What happens when Periodic acid reacts with a vicinal diol?

• It reduces the diol to an alkane

• It forms a cyclic ether

• It cleaves the carbon-carbon bond to form two carbonyls

• It forms a single carbonyl compound

How many equivalents of Periodic acid are needed to fully react with glycerol?

• Four equivalents

• Three equivalents

• Two equivalents

• One equivalent

What is the product when dihydroxyacetone is oxidized by Periodic acid?

• Ethanol

• Acetone

• Carbon dioxide

• Methanol

What is the key intermediate formed during the reaction of Periodic acid with vicinal diols?

• Cyclic anhydride

• Cyclic ether

• Cyclic ketone

• Cyclic periodate ester

What drives the cleavage of carbon-carbon bonds in the mechanism of Periodic acid?

• The formation of a cyclic anhydride

• The strength of carbonyl bonds

• The formation of a cyclic ether

• The release of hydrogen gas