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CHM624 Advanced Organic Chemistry UITM Assignment Sample, Malaysia

The CHM624 Advanced Organic Chemistry course offered at UITM (Universiti Teknologi MARA) in Malaysia is designed to provide students with a comprehensive understanding of various advanced concepts and techniques in organic synthesis. This course is particularly valuable for students who want to deepen their knowledge of organic chemistry and its applications in the creation of complex molecules.

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Assignment Task 1: Discuss the concepts in selectivity in organic chemistry, oxidation, reduction, protecting groups and carbon-carbon bond formation.

  1. Selectivity in Organic Chemistry: Selectivity in organic chemistry refers to the ability to control and direct chemical reactions to produce a specific desired product while minimizing the formation of unwanted byproducts. It is a fundamental concept in synthesis, as it enables chemists to design efficient and precise reactions. Factors influencing selectivity include reactivity, regioselectivity (site-specific reactions), chemoselectivity (specific functional group reactions), and stereoselectivity (specific geometric isomer formation).
  2. Oxidation: Oxidation is a chemical process in which a substance loses electrons, leading to an increase in its oxidation state. It often involves the addition of oxygen or removal of hydrogen from a molecule. Oxidation reactions can convert organic compounds from lower oxidation states (e.g., alkanes) to higher oxidation states (e.g., alcohols, ketones, carboxylic acids). Common reagents for oxidation include permanganates, chromates, and various oxidizing agents.
  3. Reduction: Reduction is the opposite of oxidation, involving the gain of electrons and a decrease in the oxidation state of a substance. It typically results in the conversion of functional groups such as carbonyl groups into alcohols or alkenes into alkanes. Common reducing agents include metal catalysts (e.g., hydrogenation with H2), hydride reagents (e.g., NaBH4), and metal-ammonia reduction (e.g., LiAlH4).
  4. Protecting Groups: Protecting groups are functional groups temporarily introduced into a molecule to shield a reactive group from undesired reactions during a synthesis. They are commonly used to control selectivity, enabling chemists to work on specific parts of a molecule without affecting other sensitive functional groups. Protecting groups are usually removable under specific conditions. For example, acetal protecting groups can be used to protect aldehydes or ketones.
  5. Carbon-Carbon Bond Formation: Carbon-carbon bond formation is a central process in organic synthesis, as it is the basis for building complex organic molecules. Several methods and reactions can be employed to create these bonds, including:
    Electrophilic Addition: In reactions like the Grignard reaction or nucleophilic              addition, a carbon nucleophile attacks an electrophilic carbon atom, forming a new C-C bond.
    Substitution Reactions: Reactions such as the Williamson ether synthesis and nucleophilic substitution involve replacing a leaving group with a nucleophile, forming C-C bonds.
    Condensation Reactions: These reactions, including aldol and Claisen condensations, involve the removal of a small molecule (usually water) to form a C-C bond.
    Cross-Coupling Reactions: Examples like the Suzuki-Miyaura and Heck reactions allow the coupling of two distinct carbon-containing groups to form C-C bonds, often catalyzed by transition metals.

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Assignment Task 2: To describe processes involved in the syntheses of complex molecules by applying the concepts of organic chemistry.

Complex molecule synthesis involves applying the concepts of selectivity, oxidation, reduction, protecting groups, and carbon-carbon bond formation to create intricate organic compounds. Here’s an outline of the processes involved:

  • Design and Planning: Begin by designing a synthetic route, considering the desired complex molecule’s structure and the functional groups it should contain. Identify key functional groups and potential reactions that will be crucial.
  • Selectivity Control: Plan reactions to achieve high selectivity, ensuring that desired transformations occur without unwanted side reactions. This often involves choosing appropriate reagents and conditions.
  • Protection and Deprotection: If sensitive functional groups are present, protect them with suitable protecting groups. These can be selectively removed when necessary, exposing the protected functional groups for further transformations.
  • Oxidation and Reduction: Apply oxidation and reduction reactions to introduce or modify specific functional groups as required for the target molecule. Ensure that the reactions are carried out selectively to avoid unwanted changes.
  • Carbon-Carbon Bond Formation: Utilize various methods for forming carbon-carbon bonds, such as electrophilic addition, substitution, condensation, or cross-coupling reactions. These bond-forming steps are crucial for building the complex structure.
  • Purification and Isolation: Purify the reaction mixture to separate the desired product from impurities. Techniques such as column chromatography, crystallization, or distillation can be used.
  • Characterization: Analyze the synthesized molecule using spectroscopic and analytical techniques like NMR, IR, and mass spectrometry to confirm its structure.
  • Optimization: Refine the synthetic process to improve yield, selectivity, and efficiency. This may involve adjusting reaction conditions, reagents, or the sequence of reactions.
  • Scale-Up: If necessary, scale up the synthesis to produce larger quantities of the complex molecule for further research or applications.
  • Safety and Environmental Considerations: Ensure that the synthesis is conducted safely and adheres to environmental regulations, especially when dealing with hazardous reagents.

Assignment Task 3: To perform laboratory experiments related to Wittig reaction, Friedel-Crafts acylation and oxidation reaction.

In this task, we will describe the laboratory procedures for three different organic chemistry reactions: the Wittig reaction, Friedel-Crafts acylation, and an oxidation reaction. Please note that safety precautions and lab protocols must always be followed when conducting experiments.

Experiment 1: Wittig Reaction

Aim: To synthesize an alkene from an aldehyde or ketone using the Wittig reaction.

Materials:

  • Aldehyde or ketone (e.g., benzaldehyde)
  • Phosphonium ylide (e.g., triphenylphosphine methylide)
  • Solvent (e.g., diethyl ether)
  • Reaction vessel (e.g., round-bottom flask)
  • Distillation apparatus
  • Cooling bath
  • Reagents for workup (e.g., aqueous acid and organic solvent)

Procedure:

  • Set up a round-bottom flask in a cooling bath.
  • Add the aldehyde or ketone to the flask.
  • Add the phosphonium ylide to the flask.
  • Stir the mixture for a specific reaction time.
  • After the reaction is complete, add aqueous acid to quench the reaction.
  • Extract the organic product with an organic solvent.
  • Dry the organic phase and evaporate the solvent.
  • Isolate and purify the alkene by distillation.

Experiment 2: Friedel-Crafts Acylation

Aim: To acylate an aromatic compound using Friedel-Crafts acylation.

Materials:

  • Aromatic compound (e.g., benzene)
  • Acylating agent (e.g., acetyl chloride)
  • Lewis acid catalyst (e.g., aluminum chloride)
  • Solvent (e.g., dichloromethane)
  • Reaction vessel (e.g., round-bottom flask)
  • Cooling bath
  • Reagents for workup (e.g., aqueous acid)

Procedure:

  • Set up a round-bottom flask in a cooling bath.
  • Add the Lewis acid catalyst to the flask.
  • Add the solvent and aromatic compound.
  • Slowly add the acylating agent while stirring.
  • Continue stirring for a specified reaction time.
  • After the reaction is complete, quench with aqueous acid.
  • Extract the organic product with an organic solvent.
  • Dry the organic phase and evaporate the solvent.
  • Purify the acylated product, if needed.

Experiment 3: Oxidation Reaction

Aim: To perform an oxidation reaction to convert a primary alcohol to an aldehyde or carboxylic acid.

Materials:

  • Primary alcohol (e.g., ethanol)
  • Oxidizing agent (e.g., potassium dichromate, sulfuric acid)
  • Solvent (e.g., water)
  • Reaction vessel (e.g., round-bottom flask)
  • Distillation apparatus
  • Cooling bath
  • Reagents for workup (e.g., sodium bisulfite solution)

Procedure:

  • Set up a round-bottom flask with a cooling bath and distillation apparatus.
  • Add the primary alcohol to the flask.
  • Add the oxidizing agent (e.g., potassium dichromate) and an appropriate solvent.
  • Stir the mixture and heat it gently under reflux for a specific time.
  • Cool the reaction mixture and add water.
  • Isolate the organic layer and dry it with a drying agent.
  • Distill the product to separate and collect it.
  • If necessary, react with sodium bisulfite solution to purify the aldehyde.

Always ensure you follow proper safety protocols, including wearing appropriate protective gear and working in a well-ventilated area. Additionally, make sure to dispose of waste materials in accordance with laboratory guidelines and local regulations.

Assignment Task 4: Demonstrate communication skills related to Wittig reaction, Friedel-Crafts acylation and oxidation reaction.

In a laboratory setting, effective communication is crucial for conveying information about experiments, sharing results, and ensuring safety. Here, I’ll demonstrate how to communicate about the Wittig reaction, Friedel-Crafts acylation, and oxidation reaction in a concise and informative manner.

Wittig Reaction:

  • Materials: “The materials used included benzaldehyde, triphenylphosphine methylide, diethyl ether as a solvent, a round-bottom flask, and distillation apparatus.”
  • Procedure: “In a cooled round-bottom flask, we combined benzaldehyde and triphenylphosphine methylide. The mixture was stirred for 1 hour. The reaction was quenched with aqueous acid, and the organic product was extracted with diethyl ether.”
  • Results: “The isolated product, styrene, was obtained after distillation. The yield was XX%.”
  • Safety: “Safety precautions included wearing lab coats, safety goggles, and gloves. The reaction was performed in a well-ventilated area.”

Friedel-Crafts Acylation:

  • Materials: “We used benzene, acetyl chloride as the acylating agent, aluminum chloride as the Lewis acid catalyst, dichloromethane as the solvent, a round-bottom flask, and a cooling bath.”
  • Procedure: “Benzene and the Lewis acid catalyst were mixed in a round-bottom flask in a cooling bath. Acetyl chloride was added dropwise with stirring, and the reaction proceeded for 2 hours. Aqueous acid was used to quench the reaction.”
  • Results: “The acylated product, acetophenone, was isolated after extraction and drying. The yield was XX%.”
  • Safety: “Safety measures included using safety goggles, lab coats, and gloves. The reaction was performed in a fume hood for proper ventilation.”

Oxidation Reaction:

  • Materials: “We utilized ethanol as the primary alcohol, potassium dichromate as the oxidizing agent, sulfuric acid, water, a round-bottom flask, and a distillation apparatus.”
  • Procedure: “Ethanol was mixed with potassium dichromate and sulfuric acid in a round-bottom flask. The mixture was refluxed for 3 hours and then cooled. Water was added, and the organic layer was dried with drying agents. Distillation was employed to isolate the aldehyde.”
  • Results: “Acetaldehyde was obtained as the product after distillation. The yield was XX%.”
  • Safety: “We ensured safety by wearing lab coats, safety goggles, and gloves. The reaction was carried out under a fume hood, and waste chemicals were disposed of properly.”

Effective communication in a laboratory setting involves clearly stating the purpose, materials, procedure, results, and safety precautions of an experiment. It ensures that the experiment can be replicated, understood, and conducted safely by others.

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