Organic Reaction: CrO3/HOAc Breakdown of R-CH=CH-C=_CH

[chaoseverlasting]

Homework Statement

R-CH=CH-C=_CH in presense of CrO3 and HOAc gives R-COOH+ CH=_C-COOH

The Attempt at a Solution

Can someone please explain this reaction to me? Seems like the double bond was broken and replaced with a =O. Almost like ozonolysis except the triple bond wasnt touched.

 

[chaoseverlasting]

SomebodY? Please?

 

[Blueshift5]

The reaction you have described is known as the Jones oxidation, which is a common organic reaction used to convert alkenes (R-CH=CH-R) to carboxylic acids (R-COOH). In this reaction, the chromium trioxide (CrO3) acts as an oxidizing agent, while the acetic acid (HOAc) serves as a solvent and proton source.

The first step of the reaction involves the formation of a chromate ester intermediate, where the chromium atom is attached to one of the carbon atoms in the double bond. This intermediate is then attacked by a water molecule, leading to the formation of a chromate ester with a hydroxyl group attached to the chromium atom. This hydroxyl group is then protonated by acetic acid, forming a chromic acid (H2CrO4) intermediate.

The chromic acid intermediate then reacts with the other carbon atom in the double bond, leading to the formation of a carboxylic acid functional group. This reaction involves the cleavage of the double bond and the formation of a carbonyl group (C=O). The final product is a carboxylic acid with the same carbon chain as the original alkene.

Overall, the Jones oxidation is a useful reaction for converting alkenes to carboxylic acids, which are important functional groups in organic chemistry. It is important to note that this reaction only works for alkenes with at least one hydrogen atom attached to the carbon atoms in the double bond. Alkenes with no hydrogen atoms (such as alkynes) will not undergo this reaction.