Chapter 27: Problem 68
\(\mathrm{A} \frac{\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}}{\mathrm{H}_{2} \mathrm{SO}_{4}}-\mathrm{B} \underset{\text { vigrous oxidation }}{[\mathrm{O}]} \mathrm{CH}_{3} \mathrm{COOH}\) Here, \(\mathrm{B}\) is propanone so A will be (a) Ethyl alcohol (b) Isopropyl alcohol (c) n-propyl alcohol (d) tertiary butyl alcohol
Short Answer
Step by step solution
Identify Reaction Type
Determine Initial Reactant B
Find Required Alcohol for B
Verify Compatibility with Choices
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Oxidizing Agents
In the context of alcohol oxidation, such agents include potassium dichromate ( {K_2Cr_2O_7} ) along with sulfuric acid ( {H_2SO_4} ). When used together, this mixture becomes a powerful oxidizing agent, capable of converting alcohols to ketones, aldehydes, or even acids depending on the conditions and the type of alcohol.
- Primary alcohols are often oxidized completely to carboxylic acids.
- Secondary alcohols typically stop at the ketone stage.
- Tertiary alcohols usually resist oxidation without breaking the carbon skeleton.
Organic Chemistry Reactions
One key type of reaction in organic chemistry is oxidation, where a molecule loses electrons, often involving the addition of oxygen or removal of hydrogen.
In the scenario described, an alcohol undergoes oxidation with the assistance of {K_2Cr_2O_7} and {H_2SO_4} to form a ketone, which further oxidizes to an acid. These changes are representative of multiple steps in organic transformations:
- Mild oxidation can convert secondary alcohols to ketones.
- Further oxidation can lead ketones to become acids.
Ketone Formation
In this process, the secondary alcohol loses hydrogen atoms and forms a carbonyl group (C=O), resulting in a ketone.
An example is isopropyl alcohol ( {CH_3CHOHCH_3} ), which oxidizes to form propanone, also known as acetone ( {CH_3COCH_3} ).
Considerations during ketone formation include:
- Choice of oxidizing agents to control reaction progression.
- Reaction conditions to prevent over-oxidation.
Acetic Acid Production
In vigorous oxidation conditions, such as those involving potassium dichromate ( {K_2Cr_2O_7} ) and sulfuric acid ( {H_2SO_4} ), acetone can be oxidized to form acetic acid ( {CH_3COOH} ).
This conversion emphasizes the significant transformation potential of secondary alcohols into acids. The overall process includes:
- Initial oxidation to form a ketone intermediate.
- Further oxidation under more rigorous conditions to yield acetic acid.