Chapter 13: Problem 34
Nitrobenzene gives N-phenylhydroxyl-amine by: (a) \(\mathrm{H}_{2} / \mathrm{Pd}-\mathrm{C}\) (b) \(\mathrm{Sn} / \mathrm{HCl}\) (c) \(\mathrm{Zn} / \mathrm{NH}_{4} \mathrm{Cl}\) (d) \(\mathrm{Zn} / \mathrm{NaOH}\)
Short Answer
Expert verified
Nitrobenzene gives N-phenylhydroxyl-amine by using option (d) Zn/NaOH.
Step by step solution
01
Identify the Reaction
We need to find the reducing agent that can convert nitrobenzene into N-phenylhydroxylamine. This process involves reducing the nitro group (-NO2) to an amino group (-NH2) with an additional hydroxyl (-OH) group.
02
Review the Options and Their Outcomes
Option (a) using H2 and Pd-C is a typical reduction method, but it usually reduces the nitro group to an amine without introducing a hydroxyl group. Option (b) using Sn/HCl and option (c) using Zn/NH4Cl are classical reduction methods that can reduce nitro compounds to their corresponding amines. Lastly, option (d) using Zn/NaOH is known to reduce nitrobenzene specifically to N-phenylhydroxylamine, which adds both amino and hydroxyl functionalities.
03
Select the Correct Option
Based on the known outcomes of each reducing agent, the most appropriate choice is (d) Zn/NaOH as it specifically converts nitrobenzene to N-phenylhydroxylamine via a two-step reduction process.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
N-Phenylhydroxylamine Synthesis
N-Phenylhydroxylamine is an organic compound with a significant role in various chemical reactions. Its synthesis typically involves the reduction of nitrobenzene, which is a process where the nitro group (o2) is converted into an amino group (-NH2) with an additional hydroxyl (-OH) group attached.
The reduction of nitrobenzene to N-phenylhydroxylamine can be achieved using several reagents; however, the choice of reagent influences the product. While methods using tin (Sn) and hydrochloric acid (HCl) or zinc (Zn) and ammonium chloride (NH4Cl) can effectively reduce nitro compounds to their corresponding amines, they are not typically employed for synthesizing N-phenylhydroxylamine. The key process that successfully synthesizes N-phenylhydroxylamine from nitrobenzene involves the use of zinc (Zn) in a basic medium like sodium hydroxide (NaOH).
This process is distinguished by its ability to carefully control the reduction steps required to form the N-phenylhydroxylamine rather than fully reducing the nitro group to an amine. This level of specificity is pivotal in achieving the desired chemical structure.
The reduction of nitrobenzene to N-phenylhydroxylamine can be achieved using several reagents; however, the choice of reagent influences the product. While methods using tin (Sn) and hydrochloric acid (HCl) or zinc (Zn) and ammonium chloride (NH4Cl) can effectively reduce nitro compounds to their corresponding amines, they are not typically employed for synthesizing N-phenylhydroxylamine. The key process that successfully synthesizes N-phenylhydroxylamine from nitrobenzene involves the use of zinc (Zn) in a basic medium like sodium hydroxide (NaOH).
This process is distinguished by its ability to carefully control the reduction steps required to form the N-phenylhydroxylamine rather than fully reducing the nitro group to an amine. This level of specificity is pivotal in achieving the desired chemical structure.
Organic Chemistry Reactions
In organic chemistry, reactions are the cornerstone of synthesizing new molecules and understanding how different substances interact under various conditions. Understanding the mechanics behind these reactions is essential for students and researchers alike.
Reduction reactions, such as the conversion of nitrobenzene to N-phenylhydroxylamine, are integral to organic synthesis. These reactions involve the gain of electrons by a molecule and often the addition of hydrogen atoms. Reduction can create complex molecules by altering specific functional groups, which are collections of atoms within molecules that have distinct chemical behaviors.
The complexity of a molecule's functional group dictates the course of the reduction. For instance, the nitro group in nitrobenzene is quite challenging, requiring a strong reducing agent and precise conditions to be converted to an N-phenylhydroxylamine. Each reducing agent has its mechanism of action, which affects the outcome of the reaction and showcases the intricate balance of conditions and reagents that enable the synthesis of specific compounds in organic chemistry.
Reduction reactions, such as the conversion of nitrobenzene to N-phenylhydroxylamine, are integral to organic synthesis. These reactions involve the gain of electrons by a molecule and often the addition of hydrogen atoms. Reduction can create complex molecules by altering specific functional groups, which are collections of atoms within molecules that have distinct chemical behaviors.
The complexity of a molecule's functional group dictates the course of the reduction. For instance, the nitro group in nitrobenzene is quite challenging, requiring a strong reducing agent and precise conditions to be converted to an N-phenylhydroxylamine. Each reducing agent has its mechanism of action, which affects the outcome of the reaction and showcases the intricate balance of conditions and reagents that enable the synthesis of specific compounds in organic chemistry.
NEET Chemistry Preparation
Preparing for competitive exams such as the National Eligibility cum Entrance Test (NEET) requires a deep understanding of chemistry concepts, including organic chemistry reactions like the reduction of nitrobenzene. A firm grasp of such key synthetic processes is crucial for students aiming to excel in exams.
To prepare effectively for NEET chemistry, students should focus on understanding the principles behind each reaction, the nature and behavior of various reagents, and the outcomes they produce. Knowing why zinc in a sodium hydroxide solution specifically yields N-phenylhydroxylamine from nitrobenzene, as opposed to other reducing agents, can help sharpen a student's problem-solving skills.
Additionally, practicing with various reaction scenarios, reviewing mechanisms, and solving past question papers are excellent ways to solidify knowledge and improve performance. A solid strategy for NEET preparation would include a mix of theoretical study, practical application through exercises, and continuous self-assessment to identify areas needing improvement.
To prepare effectively for NEET chemistry, students should focus on understanding the principles behind each reaction, the nature and behavior of various reagents, and the outcomes they produce. Knowing why zinc in a sodium hydroxide solution specifically yields N-phenylhydroxylamine from nitrobenzene, as opposed to other reducing agents, can help sharpen a student's problem-solving skills.
Additionally, practicing with various reaction scenarios, reviewing mechanisms, and solving past question papers are excellent ways to solidify knowledge and improve performance. A solid strategy for NEET preparation would include a mix of theoretical study, practical application through exercises, and continuous self-assessment to identify areas needing improvement.