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Mobile App Chapter 15: Problem 16
Suggest synthetic procedures leading to each of these compounds. You may start with benzene, any inorganic reagent, and organic compounds containing no more than five carbon atoms.
Short Answer
Expert verified
Use benzene and allowed reagents step-by-step to reach the target compounds through known reactions like nitration, alkylation, and Friedel-Crafts processes.
Step by step solution
01
Identify the Target Compound
Determine the structures of the compounds to which synthetic routes are needed.
02
Understand the Starting Materials
You are allowed to start with benzene, any inorganic reagent, and organic compounds containing no more than five carbon atoms.
03
Plan the Synthesis for Compound 1
Sketch the synthetic pathway for the first compound from benzene using allowed reagents. Identify the key reactions such as nitration, halogenation, Friedel-Crafts alkylation/acylation, etc.
04
Execute Steps for Compound 1
Write step-by-step the reactions involved. For example, if the target is ethylbenzene, perform the Friedel-Crafts alkylation using benzene and ethyl chloride in the presence of AlCl3.
05
Plan the Synthesis for Compound 2
Sketch the synthetic pathway for the second compound similarly using benzene, and identify relevant reactions.
06
Execute Steps for Compound 2
Write the detailed reaction steps involved. Ensure to use inorganic or organic reagents with no more than five carbons appropriately.
07
Validate Each Step
Check each transformation to be sure all are chemically feasible and comply with the given conditions.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Benzene Derivatives
Benzene and its derivatives are fundamental to understanding organic synthesis. Benzene, a simple aromatic compound, is often a starting material in synthetic reactions. Derivatives of benzene are compounds derived from benzene by substituting one or more hydrogen atoms with functional groups, such as nitro (-NO2), halide (e.g., -Cl, -Br), or alkyl (e.g., -CH3, -C2H5) groups. These substitutions alter the chemical properties of benzene, making it useful for creating a variety of organic products.
Common benzene derivatives include:
Common benzene derivatives include:
- Toluene (methylbenzene)
- Chlorobenzene
- Nitrobenzene
- Phenol (hydroxybenzene)
Friedel-Crafts Reactions
Friedel-Crafts reactions are pivotal in creating complex organic molecules from benzene. There are two main types: alkylation and acylation.
Friedel-Crafts Alkylation: This reaction introduces an alkyl group into the benzene ring by reacting benzene with an alkyl halide in the presence of a strong Lewis acid catalyst, such as AlCl3. For example, to synthesize ethylbenzene, benzene reacts with ethyl chloride (C2H5Cl) in the presence of AlCl3.
Friedel-Crafts Acylation: This reaction attaches an acyl group to benzene, using an acyl chloride in the presence of AlCl3. It's useful for adding carbonyl compounds to benzene. Both reactions expand the versatility of benzene, allowing the creation of a wide range of aromatic compounds.
Friedel-Crafts Alkylation: This reaction introduces an alkyl group into the benzene ring by reacting benzene with an alkyl halide in the presence of a strong Lewis acid catalyst, such as AlCl3. For example, to synthesize ethylbenzene, benzene reacts with ethyl chloride (C2H5Cl) in the presence of AlCl3.
Friedel-Crafts Acylation: This reaction attaches an acyl group to benzene, using an acyl chloride in the presence of AlCl3. It's useful for adding carbonyl compounds to benzene. Both reactions expand the versatility of benzene, allowing the creation of a wide range of aromatic compounds.
Synthetic Organic Chemistry
Synthetic organic chemistry involves designing and executing a path to create complex organic molecules from simpler ones. It's like solving a chemical puzzle. Here are essential steps in planning a synthesis:
- Identify the target molecule's structure.
- Determine accessible starting materials, like benzene and small organic or inorganic compounds.
- Sketch a pathway of reactions, such as nitration, halogenation, or Friedel-Crafts reactions.
- Execute each step methodically, ensuring feasibility and proper reagent use.
Nitration of Benzene
Nitration is a key reaction in synthetic chemistry for introducing a nitro group (-NO2) into the benzene ring. This process uses a mixture of concentrated nitric acid (HNO3) and sulfuric acid (H2SO4) to generate the nitronium ion (NO2+), which is the active nitrating species.
The reaction proceeds as follows:
The reaction proceeds as follows:
- Generate the nitronium ion: HNO3 + H2SO4 → NO2+ + HSO4- + H2O
- Electrophilic aromatic substitution: Benzene + NO2+ → Nitrobenzene
Halogenation Reactions
Halogenation is a fundamental reaction in the modification of benzene, introducing a halogen atom to the aromatic ring. Commonly, chlorine (Cl) and bromine (Br) are used.
In halogenation, benzene undergoes electrophilic aromatic substitution, facilitated by a Lewis acid catalyst, such as FeCl3 or AlCl3. The general process is:
In halogenation, benzene undergoes electrophilic aromatic substitution, facilitated by a Lewis acid catalyst, such as FeCl3 or AlCl3. The general process is:
- Generate the electrophile: X2 + FeX3 → X+ + FeX4- (where X is Cl or Br)
- Substitute on benzene: Benzene + X+ → Halobenzene
