Question

The compounds which can evolve two mole of \(\mathrm{CO}_{2}\) on oxidative ozonolysis followed by heating is (A) C1=CCCC=C1 (B) C=C1CCCCC1C=CC (C) C=C1CCCC(=C)C1 (D) C=C(C)C

Short answer

The compound which can evolve two moles of CO₂ on oxidative ozonolysis followed by heating is Compound B: C=C1CCCCC1C=CC.

Step-by-step solution

Understand Ozonolysis Process

Ozonolysis is a process in which ozone (O₃) is used to break the carbon-carbon double bond (C=C) present in alkenes. It is an oxidative process followed by a reductive or oxidative workup. In this case, we have an oxidative workup followed by heating. When oxidative ozonolysis is performed on a compound containing carbon-carbon double bonds, it cleaves the double bond and adds an oxygen atom to each carbon, creating carbonyl compounds (aldehyde or ketone).

Analyze Compound A

Compound A is a benzene ring: C1=CCCC=C1 Since there are no carbon-carbon double bonds outside the aromatic ring structure, no ozonolysis will take place, and no CO₂ will be evolved. The benzene structure is stable and will not be cleaved by oxidative ozonolysis.

Analyze Compound B

Compound B is an alkene with two double bonds: C=C1CCCCC1C=CC Upon oxidative ozonolysis, the two double bonds will be cleaved, creating carbonyl compounds. In this case, the compound released two moles of CO₂ upon oxidative workup and heating. The result is that Compound B meets the condition and can evolve two moles of CO₂ upon ozonolysis.

Analyze Compound C

Compound C has a double bond in the ring as well as a double bond in the side chain: C=C1CCCC(=C)C1 Performing oxidative ozonolysis on this compound will lead to the cleavage of both double bonds, and each carbon in the double bond will be bonded to an oxygen atom. However, upon further analysis, we find that only one mole of CO₂ will be evolved from this compound.

Analyze Compound D

Compound D is a simple alkene with a single carbon-carbon double bond: C=C(C)C In this case, oxidative ozonolysis will break the double bond, and oxygen will be added to each carbon atom. However, only one mole of CO₂ will be evolved from this compound.

Conclusion

Based on the analysis of the given compounds, we can conclude that the compound which can evolve two moles of CO₂ on oxidative ozonolysis followed by heating is Compound B: C=C1CCCCC1C=CC

Key concepts

Oxidative Ozonolysis

Ozonolysis is a reaction where ozone ( O₃ ) is used to break double bonds in alkenes. For this process, ozone interacts with carbon-carbon double bonds (C=C ) and splits them apart. After splitting, each carbon involved in the double bond forms a new bond with oxygen. That's why it's called oxidative ozonolysis—the double bonds are oxidatively cleaved. This reaction often results in the formation of carbonyl compounds. When followed by oxidative workup, which means the treatment of ozonides with an oxidizing agent, complex aldehydes or ketones are typically produced. It's crucial to note that different types of workups can impact the final products formed.

Carbon-Carbon Double Bond Cleavage

The heart of the ozonolysis reaction is the cleavage of carbon-carbon double bonds. When ozone is added to an alkene, it specifically targets these double bonds, resulting in the addition of oxygen to each carbon atom involved. Upon breaking the double bond, the molecule is effectively split into two separate parts, with each part getting a carbonyl oxygen added. This transformation is crucial because it's the stage where the original structure of the alkene is altered, paving the way for new compounds to form. Thus, the cleavage of these bonds not only changes the molecular structure but also leads to the release of smaller gaseous molecules, under further reactions.

Generation of Carbonyl Compounds

As a result of oxidative ozonolysis, carbonyl compounds are generated. Carbonyls are characterized by a carbon atom double-bonded to an oxygen atom, forming functional groups like aldehydes and ketones. The specific carbonyl compounds formed depend on the original structure of the alkene involved in the reaction. Depending on the type and location of the double bonds in the original compound, multiple carbonyl products may be formed. These compounds are significant in organic chemistry because they serve as building blocks for more complex molecules and reactions. Therefore, the generation of carbonyl compounds is a fundamental outcome of the ozonolysis process.

Evolution of CO2 upon Heating

After the oxidative workup in ozonolysis, heating the product can cause the evolution of carbon dioxide ( CO₂ ). This is because some of the carbonyl compounds formed in ozonolysis may further decompose or react when heated. For instance, in the right conditions, carboxylic acids can decarboxylate, releasing CO₂ as a by-product. This reaction is crucial for certain compounds, as it demonstrates how CO₂ evolution can be used to signify complete transformations post-ozonolysis. Understanding the evolution of CO₂ in this context is fundamental, as it can offer insights into the stability and reactivity of the resultant products after ozonolysis.