Chapter 6: Problem 40
An aromatic compound ' \(\mathrm{A}^{\prime} \mathrm{C}_{7} \mathrm{H}_{6} \mathrm{Cl}_{2}\), gives \(\mathrm{AgCl}\) on boiling with alcoholic \(\mathrm{AgNO}_{3}\) solution and yields \(\mathrm{C}_{7} \mathrm{H}_{7} \mathrm{OCl}\) on treatment with \(\mathrm{NaOH}\). 'A' on oxidation gives monochloro benzoic acid which affords only one mononitro derivative. The compound ' \(A^{\prime}\) is
Short Answer
Step by step solution
Analyze Given Information
Determine Reactivity with AgNO3
Reaction with NaOH Insight
Oxidation Leads to Chlorobenzoic Acid
Mononitro Derivative Formation
Identify Compound 'A'
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Organic Chemistry Reactions
- Addition Reactions: Occur when two or more molecules combine to form a larger one.
- Elimination Reactions: Involve the removal of a small molecule from a larger molecule, resulting in a double bond or ring formation.
- Substitution Reactions: A atom or group in a molecule is replaced by another atom or group.
- Rearrangement Reactions: The structure of a molecule is rearranged to form an isomer.
Halogenation
During halogenation, a halogen can add directly to a carbon atom, often resulting in significant changes to the molecule's reactivity and overall properties. There are two main ways this occurs:
- Direct Halogenation: The halogen molecule reacts directly with the compound, often requiring a catalyst to proceed.
- Halogen Exchange: One halogen is replaced by another via a substitution reaction, as seen in aromatic hydrocarbon transformations.
Substitution Reactions
For aromatic compounds, electrophilic substitution is common, where an electrophile replaces a hydrogen atom in the aromatic ring. Meanwhile, nucleophilic substitutions involve nucleophiles attacking and replacing a substituent, often seen in alkyl halides.
In the presented exercise, substitution is evident when 'A' reacts with \\(\mathrm{NaOH}\), replacing a chlorine with an -OH group to form an alcohol. This type of reaction showcases the principle that different conditions (like presence of a nucleophile) can guide the direction of substitution.
Oxidation of Aromatics
Aromatic oxidation typically transforms hydrocarbons into carboxylic acids, altering their chemical behavior significantly. A common example includes the oxidation of alkyl side chains on benzene rings to yield benzoic acids.
- Monochloro compounds, when oxidized, can form chlorobenzoic acids, retaining the halogen as part of their structure.
- The position of substituents influences the oxidation process and the types of products formed.