Question

An organic compound \(\left(\mathrm{C}_{6} \mathrm{H}_{10}\right)\), on treatment with ozone in the presence of zinc and water gives \(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}_{2}\), which on O=CC1=CCCCC1 further treatment with base followed by acidification under hot conditions gives \(\mid \quad\). Write the sequence of reactions.

Short answer

The final product after acidification under hot conditions is denoted as "product |." Unfortunately, it cannot be explicitly identified without more information regarding specific compounds or the structure of the starting alkene. Follow the steps outlined to write the sequence of reactions for this organic compound.

Step-by-step solution

Identify the Initial Compound

Since the compound has a molecular formula of C6H10, it could be an alkene with a double bond, making it an unsaturated hydrocarbon.

Perform Ozonolysis Reaction

Ozonolysis is a process in which alkene double bonds are cleaved and replaced by oxygen groups when treated with ozone (O3). The reaction of C6H10 with ozone will breakdown the double bond and form C6H10O2. In this case, the compound reacts with ozone in the presence of reducing agents such as zinc and water, which doesn't allow the formation of carbonyl compounds. This reaction is known as "reductive ozonolysis."

Base Treatment

First, the compound is treated with a base. The base abstracts a proton from the hydroxy group, giving the oxygen a negative charge.

Acidification Under Hot Conditions

Finally, the reaction goes through an acidification under hot conditions, which usually involves the addition of an acid (H+) to the negatively charged oxygen obtained in the previous step.

Write the sequence of reactions

Here's the complete sequence of reactions for this exercise: 1. Start with C6H10 (alkene compound) 2. Perform reductive ozonolysis with O3, Zn, and H2O → C6H10O2 3. Treat with a base → C6H9O2- 4. Acidification under hot conditions → | (product) Following these steps, you can successfully visualize and write the sequence of reactions for this organic compound.

Key concepts

Reductive Ozonolysis

A critical reaction in organic chemistry is reductive ozonolysis, which is commonly used to cleave double bonds in alkenes. When an alkene undergoes ozonolysis, the double bond reacts with ozone (\( O_3 \)) to form an ozonide, which is an unstable intermediate. To isolate the final products, the ozonide is reduced.

In the case of reductive ozonolysis, reducing agents like zinc (\( Zn \)) and water (\( H_2O \)) are used. This gentle reduction converts the ozonide into carbonyl compounds without forming free carbonyl radicals, which prevents further oxidation. The resulting carbonyl compounds can be aldehydes, ketones, or a combination of both, depending on the alkene's substitution pattern. This specificity makes reductive ozonolysis a valuable tool for determining the structure of alkenes and for synthesizing complex molecules from simpler precursors.

Organic Reaction Mechanisms

Understanding how and why organic reactions occur is the foundation of organic chemistry. Organic reaction mechanisms provide a step-by-step description of all the stages that take place during a chemical reaction, including bond-breaking and bond-making events.

A thorough grasp of these reaction mechanisms is vital for predicting the outcome of reactions and for designing new synthetic routes in organic synthesis. In the context of ozonolysis, for instance, we observe a mechanism that includes several stages: the formation of an ozonide intermediate, its reduction, and the final conversion to carbonyl compounds. By analyzing each step, chemists can manipulate reaction conditions to steer the reaction towards desired products. Mechanistic understanding also aids in diagnosing problems when reactions do not proceed as expected.

Acid-Base Reactions in Organic Chemistry

Acid-base reactions are ubiquitous in organic chemistry and are pivotal in a variety of chemical processes. These reactions involve the transfer of protons (\( H^+ \)) between molecules. A base is a substance that can accept a proton, while an acid is one that can donate a proton.

The outcome of acid-base reactions can have profound effects on the structure and reactivity of an organic compound. For example, after a reductive ozonolysis, the treatment of the resulting compound with a base results in deprotonation, leading to the formation of a negative charge on oxygen, known in this context as an alkoxide ion. Subsequent protonation during the acidification stage can lead to different products depending on the reaction conditions, such as the temperature or the presence of other functional groups in the molecule. The ability to control the outcome of such reactions is crucial for successful synthesis in organic chemistry.