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유기화학실험 oxidation

"유기화학실험 oxidation"에 대한 내용입니다.
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최초등록일 2023.07.17 최종저작일 2023.06
유기실 유기화학실험 OXIDATION 서울여자대학교
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유기화학실험 oxidation
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    소개

    "유기화학실험 oxidation"에 대한 내용입니다.

    목차

    1. subject
    2. date
    3. name
    4. principle and object
    5. material(apparatus, instruments, reagents)
    6. procedure and observation
    7. result
    8. reference

    본문내용

    -산화(Oxidation): 일반화학에서 산화란 한 개 혹은 그 이상의 전자를 잃는 것을 말하지만 유기화학에서 산화는 탄소와 그보다 더 전기음성적인 원자(주로 산소, 질소, 할로젠) 사이의 bond formation, 혹은 탄소와 그보다 덜 전기음성적인 원자(주로 수소) 사이의 bond breaking으로 탄소가 electron density를 잃는 반응을 말한다. 즉 산화란 C-O, C-N, C-X 결합이 생성되고, C-H 결합이 파괴되어 탄소의 전자밀도가 낮아지는 반응이다. Oxidation에서는 주로 산소가 첨가되고 reduction에서는 주로 수소가 첨가된다.1)

    -oxidation of alcohols: carbonyl compound의 reduction은 alcohol을 생성하고, alcohol의 oxidation은 carbonyl compound를 만든다. 다음 Figure 1.에는 alcohol의 차수에 따라 생성되는 product가 나와있다.

    -general oxidants
    ○,1 HOCl(hypochlorous acid): O-Cl 결합이 있는데O/N/F/S에 halogen이 붙어 있으면 그 결합은 매우 약하다. Figure 1.처럼 acidic condition에서 NaOCl(표백제)과 acetic acid이 반응하여 만들어진다.
    ○,2 (CH3)3COCl(t-butyl hypochlorite): O-Cl 결합이 있는데O/N/F/S에 halogen이 붙으면 그 결합은 매우 약하다.
    ○,3 H2CrO4(chromic acid): acidic하다.
    ○,4 NaCr2O7(sodium dichromate)
    ○,5 KMnO4(potassium per-manganate): aldehyde를 거쳐 carboxylic acid까지 oxidation이 진행된다.
    ○,6 HNO3(nitric acid): carbohydrate에서 사용하는 산화제이다.
    ○,7 PDC
    ○,8 PCC: 1차 알코올을 aldehyde로 보낼 때는 dry condition이고, water가 있으면 water가 공격해서 oxidant 자체가 deactivation이고 geminal diol이 된다.

    참고자료

    · John Mcmurry. Organic Chemistry. 9th edition. Cengage Learning. 2016.
    · The handout prepared by chemistry department. oxidation
    · 생화학분자생물학회. 생화학백과. 극성. https://www.ksbmb.or.kr/html/
    · Kenneth L. Williamson · Katherine M. Masters. Macroscale and Microscale organic experiments. 7th edition, Brooks/Cole. 2017.
    · 산업재해예방 안전보건공단. MSDS. Silica gel. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · 산업재해예방 안전보건공단. MSDS. Ethyl acetate. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · MERCK INDEX. Ethyl acetate. https://www.rsc.org/Merck-Index/monograph/m5081/ethyl%20acetate?q=unauthorize
    · 산업재해예방 안전보건공단. MSDS. HEXANE. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · MERCK INDEX. HEXANE. https://www.rsc.org/Merck-Index/monograph/m6002/nhexane?q=unauthorize
    · 산업재해예방 안전보건공단. MSDS. Water. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · 산업재해예방 안전보건공단. MSDS. 디클로로메탄. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · 산업재해예방 안전보건공단. MSDS. 차아염소산 나트륨. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · MERCK INDEX. 9-fluorenone. https://www.merckmillipore.com/KR/ko/product/9-Fluorenone,MDA_CHEM-803977
    · MSDS. 9-fluorenol. https://www.fishersci.com/store/msds?partNumber=AC121230250&productDescription=9-HYDROXYFLUORENE%2C+97%2B%25+25GR&vendorId=VN00032119&countryCode=US&language=en
    · 산업재해예방 안전보건공단. MSDS. 황산 마그네슘. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · 산업재해예방 안전보건공단. MSDS. Acetone. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · libretexts. Chemistry. Ice. https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Introductory_Chemistry_(CK-12)/15%3A_Water/15.02%3A_Structure_of_Ice
    · 산업재해예방 안전보건공단. MSDS. 다이메틸에테르. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · 산업재해예방 안전보건공단. MSDS. 아황산나트륨. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
    · 과학기자재 랩가이드. 가열교반기 사용법. 2019. https://blog.naver.com/labguide4574/221511802681

  • AI와 토픽 톺아보기

    • 1. Oxidation
      Oxidation is a fundamental chemical process that involves the loss of electrons by a molecule, atom, or ion. It is a crucial concept in chemistry, with wide-ranging applications in various fields, including organic synthesis, biochemistry, and materials science. Understanding the principles of oxidation is essential for predicting and controlling chemical reactions, as well as for developing new technologies and materials. The ability to selectively oxidize specific functional groups or molecules is a valuable tool in organic synthesis, allowing for the synthesis of complex organic compounds. Additionally, oxidation processes play a vital role in biological systems, where they are involved in energy production, signaling pathways, and immune responses. Gaining a deep understanding of oxidation mechanisms and the factors that influence them is crucial for advancing scientific knowledge and developing innovative solutions to complex problems.
    • 2. TLC (Thin Layer Chromatography)
      Thin Layer Chromatography (TLC) is a powerful analytical technique widely used in organic chemistry for the separation, identification, and purification of organic compounds. TLC provides a simple, rapid, and cost-effective method for analyzing the composition of complex mixtures, making it an indispensable tool in various fields, such as organic synthesis, natural product research, and pharmaceutical development. The ability to separate and visualize different components of a mixture based on their relative affinities for the stationary and mobile phases allows researchers to gain valuable insights into the chemical composition and purity of their samples. Furthermore, TLC can be used to monitor the progress of chemical reactions, optimize reaction conditions, and guide the purification of target compounds. As an accessible and versatile technique, TLC continues to be an essential part of the analytical toolkit for chemists, enabling them to make informed decisions and advance their research in a wide range of applications.
    • 3. Solvent Polarity
      Solvent polarity is a fundamental concept in chemistry that has far-reaching implications in various areas, including organic synthesis, analytical chemistry, and biochemistry. The polarity of a solvent, which is determined by the distribution of charge within its molecules, plays a crucial role in determining the solubility, reactivity, and selectivity of chemical processes. Understanding solvent polarity is essential for designing effective extraction and purification procedures, selecting appropriate solvents for chemical reactions, and predicting the behavior of molecules in biological systems. The ability to manipulate solvent polarity can also be leveraged to control the solubility, reactivity, and selectivity of organic reactions, enabling chemists to develop more efficient and selective synthetic routes. Furthermore, the study of solvent polarity has contributed to the development of green chemistry principles, as the selection of appropriate solvents can minimize environmental impact and improve the sustainability of chemical processes. Continued research and advancements in the understanding of solvent polarity will undoubtedly lead to further innovations in chemistry and related fields.
    • 4. Oxidation Reagents
      Oxidation reagents are a diverse class of chemical compounds that play a crucial role in organic synthesis, analytical chemistry, and various industrial processes. These reagents facilitate the selective oxidation of specific functional groups, allowing chemists to transform and manipulate organic molecules in a controlled manner. The development and understanding of oxidation reagents have been instrumental in the synthesis of complex organic compounds, the characterization of chemical species, and the development of new materials and technologies. The selection of the appropriate oxidation reagent is often a critical step in synthetic pathways, as it can determine the efficiency, selectivity, and overall success of the reaction. Continued research in this area has led to the discovery of novel oxidation reagents with improved selectivity, milder reaction conditions, and reduced environmental impact, contributing to the advancement of sustainable and green chemistry practices. As our understanding of oxidation mechanisms and the properties of oxidation reagents deepens, we can expect further innovations that will expand the capabilities of chemists and drive progress in a wide range of scientific and technological domains.
    • 5. Mechanism of Alcohol Oxidation
      The mechanism of alcohol oxidation is a fundamental topic in organic chemistry, with significant implications in various fields, including synthetic organic chemistry, biochemistry, and materials science. Understanding the detailed steps and factors that govern the oxidation of alcohols is crucial for designing efficient and selective synthetic routes, as well as for elucidating the role of alcohol oxidation in biological processes. The ability to selectively oxidize alcohols to aldehydes, ketones, or carboxylic acids is a valuable tool in organic synthesis, enabling the construction of complex molecules and the functionalization of existing compounds. Furthermore, the study of alcohol oxidation mechanisms has contributed to the development of new oxidation reagents and catalysts, which have expanded the scope and efficiency of these transformations. Additionally, the oxidation of alcohols is a key step in many biological pathways, such as the metabolism of ethanol and the regulation of cellular signaling. Continued research in this area will not only deepen our fundamental understanding of chemical reactivity but also lead to the development of new synthetic methodologies, improved analytical techniques, and a better understanding of the role of alcohol oxidation in biological systems.
    • 6. Pinnick Oxidation
      The Pinnick oxidation is a valuable synthetic transformation in organic chemistry, which involves the selective oxidation of aldehydes to carboxylic acids. This reaction, developed by Harold Pinnick in the 1980s, has become a widely used tool in the synthesis of complex organic molecules, particularly in the context of natural product synthesis and medicinal chemistry. The Pinnick oxidation is known for its mild reaction conditions, excellent functional group tolerance, and high selectivity, making it a preferred choice for the late-stage oxidation of sensitive intermediates. The ability to convert aldehydes to carboxylic acids without affecting other functional groups present in the molecule is a significant advantage of this transformation, as it allows for the efficient construction of more complex structures. Furthermore, the Pinnick oxidation has found applications in the synthesis of various biologically active compounds, contributing to the development of new therapeutic agents and the understanding of structure-activity relationships. As research in organic synthesis continues to evolve, the Pinnick oxidation and its variants will likely remain an important tool in the chemist's arsenal, enabling the efficient and selective construction of complex organic molecules with diverse applications.
    • 7. Dess-Martin Oxidation
      The Dess-Martin oxidation is a powerful and widely used method for the selective oxidation of alcohols to aldehydes or ketones in organic synthesis. Developed by David Dess and James Martin in the 1980s, this transformation has become a staple in the synthetic chemist's toolkit due to its reliability, functional group tolerance, and mild reaction conditions. The Dess-Martin reagent, a hypervalent iodine compound, is able to selectively oxidize primary and secondary alcohols without affecting other sensitive functional groups, making it a valuable tool in the synthesis of complex organic molecules, particularly in the context of natural product synthesis and medicinal chemistry. The ability to perform this oxidation under neutral conditions and the ease of handling the Dess-Martin reagent have contributed to its widespread adoption in both academic and industrial settings. Furthermore, the Dess-Martin oxidation has been the subject of extensive mechanistic studies, providing valuable insights into the factors that govern the selectivity and efficiency of this transformation. As organic synthesis continues to evolve, the Dess-Martin oxidation and related hypervalent iodine-based oxidation methods will likely remain an indispensable part of the synthetic chemist's toolkit, enabling the efficient and selective construction of a wide range of organic compounds with diverse applications.
    • 8. Stoichiometry Calculation
      Stoichiometry calculation is a fundamental concept in chemistry that underpins our understanding of chemical reactions and the quantitative relationships between reactants and products. This skill is essential for chemists, as it allows them to predict the amounts of starting materials required, the quantities of products formed, and the limiting reagents in a given reaction. Accurate stoichiometry calculations are crucial for the design and optimization of synthetic procedures, the characterization of chemical processes, and the development of new materials and technologies. Furthermore, the ability to perform stoichiometry calculations is a key component of many analytical techniques, such as titrations and spectrophotometric analyses, which rely on the quantitative relationships between chemical species. As chemistry continues to advance, the importance of stoichiometry calculations will only grow, as chemists strive to develop more efficient, sustainable, and scalable chemical processes. Mastering this fundamental skill not only enhances one's understanding of chemical principles but also equips chemists with the necessary tools to tackle complex problems and drive innovation in various fields, from organic synthesis to materials science and beyond.

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