• AI글쓰기 2.1 업데이트
GOLD
GOLD 등급의 판매자 자료
리포트 / 자연과학

Regiospecific epoxidation of carvone

"Regiospecific epoxidation of carvone"에 대한 내용입니다.
16 페이지
어도비 PDF
최초등록일 2024.08.22 최종저작일 2024.05
유기화학실험 유기화학 실험레포트 화학과
16P 미리보기
Regiospecific epoxidation of carvone
상세정보 자료후기 0 자주묻는질문
  • 이 자료를 선택해야 하는 이유
    이 내용은 AI를 통해 자동 생성된 정보로, 참고용으로만 활용해 주세요.
    • 논리성
    • 전문성
    • 명확성
    • 유사도 지수
      참고용 안전
    • 🧪 유기화학 실험의 상세한 메커니즘과 절차 제공
    • 🔬 Carvone의 epoxidation 반응에 대한 심층적인 이론적 배경 설명
    • 📊 실험 결과 분석 및 NMR 스펙트럼 해석 방법 상세 제시
    본 문서는 PDF문서으로 복사 및 편집이 불가합니다.

    미리보기

    소개

    "Regiospecific epoxidation of carvone"에 대한 내용입니다.

    목차

    1. Title

    2. Purpose

    3. Theory
    1) Epoxidation of alkenes by peroxy acids (mCPBA)
    2) Epoxidation of alkenes by alkaline H2O2
    3) Epoxidation of α, β-unsaturated ketone
    4) Regiospecificity, Stereoselectivity
    5) (R-/S-) Carvone / terpenes
    6) Notation of R/S (absolute configuration) & D/L (relative configuration) & (+/-) or d/l(optical rotation)
    7) Selectivity of epoxidation reaction
    8) Reaction mechanisms
    9) Column chromatography (isocratic/gradient elution chromatography, Deemter equation)

    4. Chemical and Apparatus
    1) Chemical
    2) Apparatus

    5. Procedure
    1) Synthesis(Epoxidation of (R)-(-)-Carvone by m-Chloroperoxybenzoic Acid (mCPBA))
    2) Qualitative analysis (by thin-layer chromatography)
    3) Purification (by flash chromatography)
    4) Structural characterization and quantitative analysis (by 1H NMR spectroscopy)
    5) Synthes (Epoxidation of (R)-(-)-Carvone by Alkaline H2O2)
    6) Qualitative analysis (by thin-layer chromatography)
    7) Structural characterization and quantitative analysis (by 1H NMR spectroscopy)
    8) Part C: Relationships between Reaction Selectivity and Reaction Mechanism.

    6. 실험 시 주의해야 할 사항

    7. Data& Result
    1) Product
    2) Yield
    3) TLC result
    4) NMR (300MHz NMR)

    8. Discussion

    9. Conclusion

    본문내용

    1. Title: Regiospecific epoxidation of carvone

    2. Purpose: This is a discovery-oriented experiment in which you will investigate the selectivity and the mechanism of two commonly used epoxidation reactions: Epoxidation of alkenes by peroxy acids, Epoxidation of alkenes by alkaline H2O2

    3. Theory
    i. Epoxidation of alkenes by peroxy acids (mCPBA)
    epoxidation은 epoxide를 형성하는 반응이다. 먼저 epoxide는 oxygen이 다른 탄소와 고리 형태를 만들고 있는 화합물로, oxirane이라고도 부르는 고리 형태의 ether에 해당한 다. epoxide는 유기 화합물을 합성할 때 유용한 합성 중간체로 활용될 수 있다. epoxide 를 형성하기 위해서는 alkene과 peroxy acid를 활용할 수 있다. peroxyacid는 –O-O- 결 합을 포함한 carboxylic acid로, 과산화산이라고 불리는 반응성이 좋은 화학종이다. alkene과 peroxyacid 사이에서 반응이 일어날 때 하단에 첨부한 mechanism처럼 peroxyacid는 오각형으로 배열되어 고리 중간체를 거치고 epoxide와 R-COOH의 산을 형성한다. 이 반응은 One-step 과정이며 이중결합을 가진 두 탄소가 peroxyacid의 산소 와 같은 면에 배열되는 syn 첨가 생성물을 만든다. 또한, one-step 반응의 특성 상 분자 의 회전이나 변형이 불가능하다는 특징을 갖는다. mCPBA는 m-chloroperoxybenzoic acid로 epoxidation reagent로 자주 사용된다.

    참고자료

    · Fulmer, G. R., Miller, A. J., Sherden, N. H., Gottlieb, H. E., Nudelman, A., Stoltz, B. M., ... & Goldberg, K. I. (2010). NMR chemical shifts of trace impurities: common laboratory solvents, organics, and gases in deuterated solvents relevant to the organometallic chemist. Organometallics, 29(9), 2176- 2179.
    · Mak, Kendrew & Lai, Y. & Siu, Yuk-Hong. (2006). Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions. Journal of Chemical Education - J CHEM EDUC. 83. 10.1021/ed083p1058.

  • AI와 토픽 톺아보기

    • 1. Epoxidation of alkenes by peroxy acids
      Epoxidation of alkenes by peroxy acids is a widely used organic reaction for the synthesis of epoxides, which are important intermediates in organic chemistry. This reaction involves the nucleophilic attack of the alkene on the peroxy acid, forming a cyclic transition state that leads to the formation of the epoxide product. The reaction is typically carried out using a peroxy acid such as m-chloroperoxybenzoic acid (mCPBA) in an organic solvent. The reaction is generally stereospecific, meaning that the stereochemistry of the alkene is retained in the epoxide product. The regioselectivity of the reaction can be influenced by the substituents on the alkene, with more substituted alkenes typically giving the more substituted epoxide. Overall, the epoxidation of alkenes by peroxy acids is a useful and versatile reaction in organic synthesis.
    • 2. Epoxidation of alkenes by alkaline H2O2
      The epoxidation of alkenes using alkaline hydrogen peroxide (H2O2) is another important method for the synthesis of epoxides. This reaction is typically carried out in the presence of a base, such as sodium hydroxide or potassium hydroxide, which activates the H2O2 to form a peroxide anion that can then attack the alkene. The reaction is generally less stereospecific than the epoxidation by peroxy acids, as the peroxide anion can approach the alkene from either side. However, the regioselectivity of the reaction can still be influenced by the substituents on the alkene, with more substituted alkenes typically giving the more substituted epoxide. The use of alkaline H2O2 as the oxidizing agent can be advantageous in some cases, as it is a relatively inexpensive and environmentally friendly reagent. Overall, the epoxidation of alkenes by alkaline H2O2 is a useful alternative to the peroxy acid method, with its own advantages and limitations.
    • 3. Epoxidation of α,β-unsaturated ketones
      The epoxidation of α,β-unsaturated ketones is a more challenging reaction, as the presence of the carbonyl group can affect the reactivity and selectivity of the epoxidation. In this case, the epoxidation can occur at either the alkene or the carbonyl group, depending on the reaction conditions and the substituents on the molecule. The use of peroxy acids or alkaline H2O2 can lead to the formation of both the desired epoxide and undesired side products, such as the epoxidation of the carbonyl group. Careful control of the reaction conditions, such as the choice of oxidizing agent, solvent, and temperature, is necessary to achieve the desired selectivity and yield. Additionally, the presence of the carbonyl group can influence the stereochemistry of the epoxide product, leading to potential complications in the overall synthetic strategy. Overall, the epoxidation of α,β-unsaturated ketones requires a more nuanced approach compared to the epoxidation of simple alkenes.
    • 4. Regioselectivity and stereoselectivity
      Regioselectivity and stereoselectivity are important considerations in epoxidation reactions. Regioselectivity refers to the preference for the formation of one regioisomeric epoxide over another, while stereoselectivity refers to the preference for the formation of one stereoisomeric epoxide over another. The regioselectivity of epoxidation reactions can be influenced by the substituents on the alkene, with more substituted alkenes typically giving the more substituted epoxide. The stereoselectivity of the reaction can be influenced by the choice of oxidizing agent, with peroxy acids generally giving more stereospecific reactions compared to alkaline H2O2. The presence of other functional groups, such as carbonyl groups, can also affect the regioselectivity and stereoselectivity of the epoxidation. Understanding and controlling these selectivity factors is crucial for the efficient synthesis of desired epoxide products in organic chemistry.
    • 5. R/S and D/L configurations
      The R/S and D/L configurations are important concepts in the context of epoxidation reactions, as they describe the stereochemistry of the epoxide products. The R/S system is used to assign the absolute configuration of chiral centers, while the D/L system is used to assign the configuration of stereogenic centers in carbohydrates and other biomolecules. In epoxidation reactions, the stereochemistry of the epoxide product is typically determined by the stereochemistry of the starting alkene and the mechanism of the epoxidation reaction. Peroxy acid epoxidations are generally stereospecific, meaning that the stereochemistry of the alkene is retained in the epoxide product. In contrast, epoxidation using alkaline H2O2 can be less stereospecific, leading to a mixture of epoxide stereoisomers. Understanding the R/S and D/L configurations is crucial for the interpretation of experimental data and the design of synthetic strategies involving epoxidation reactions.
    • 6. Selectivity of epoxidation reactions
      The selectivity of epoxidation reactions is a critical factor in organic synthesis, as it determines the yield and purity of the desired epoxide product. Factors that can influence the selectivity of epoxidation reactions include the choice of oxidizing agent, the presence of other functional groups, the substituents on the alkene, and the reaction conditions. Peroxy acid epoxidations are generally more stereoselective, while alkaline H2O2 epoxidations can be less selective. The presence of carbonyl groups or other functional groups can also affect the regioselectivity and stereoselectivity of the epoxidation. Careful optimization of the reaction conditions, such as the choice of solvent, temperature, and reaction time, can help to improve the selectivity of the epoxidation. Understanding and controlling the selectivity of epoxidation reactions is essential for the efficient synthesis of complex organic molecules.
    • 7. Reaction mechanisms
      The reaction mechanisms underlying epoxidation reactions are important to understand, as they can provide insights into the factors that influence the selectivity and efficiency of these transformations. The epoxidation of alkenes by peroxy acids is generally believed to proceed through a cyclic transition state, where the peroxy acid attacks the alkene in a concerted, stereospecific manner. In contrast, the epoxidation of alkenes by alkaline H2O2 is thought to involve the formation of a peroxide anion intermediate, which can attack the alkene from either side, leading to a less stereospecific reaction. The presence of other functional groups, such as carbonyl groups, can also affect the reaction mechanism, leading to the formation of undesired side products. Understanding the detailed reaction mechanisms underlying epoxidation reactions can help chemists design more efficient and selective synthetic strategies, as well as predict and rationalize the outcomes of these transformations.
    • 8. Column chromatography
      Column chromatography is a widely used technique for the purification and separation of epoxide products from epoxidation reactions. The choice of stationary phase, mobile phase, and column dimensions can all have a significant impact on the efficiency and selectivity of the chromatographic separation. For example, the use of silica gel as the stationary phase can be effective for the separation of epoxides, as the polarity of the epoxide group can interact with the silica surface. The choice of mobile phase, such as a mixture of hexane and ethyl acetate, can also be optimized to achieve the desired separation. Additionally, the scale of the reaction and the amount of material to be purified can influence the choice of column size and the overall chromatographic strategy. Careful optimization of the column chromatography conditions is essential for the efficient isolation and purification of epoxide products in organic synthesis.
    • 9. Experimental procedures and safety
      The experimental procedures and safety considerations are crucial aspects of epoxidation reactions, as these transformations can involve the use of hazardous reagents and the generation of potentially toxic or reactive intermediates. Proper safety protocols, such as the use of personal protective equipment, appropriate ventilation, and the handling of waste materials, must be followed to minimize the risks associated with these reactions. The choice of reaction conditions, such as temperature, solvent, and reaction time, can also impact the safety and efficiency of the epoxidation. Additionally, the scale-up of epoxidation reactions may require further optimization of the experimental procedures to ensure consistent and reproducible results. Careful attention to experimental details and safety considerations is essential for the successful and safe execution of epoxidation reactions in the laboratory.
    • 10. Results and discussion
      The results and discussion section of a research paper on epoxidation reactions is where the experimental findings, data analysis, and interpretation of the results are presented. This section should provide a clear and comprehensive overview of the key outcomes of the study, including the yields, selectivities, and stereochemical outcomes of the epoxidation reactions. The discussion should also address any unexpected or interesting observations, and provide a critical analysis of the factors that influenced the selectivity and efficiency of the epoxidation. Comparisons to previous literature reports, as well as the implications of the findings for the broader field of organic synthesis, should also be included. The results and discussion section is crucial for the dissemination of the research findings and the advancement of the understanding of epoxidation reactions and their applications in organic chemistry.

  • 자료후기

      Ai 리뷰
      이 실험은 carvone의 두 가지 다른 특성의 이중결합에서 일어나는 epoxidation 반응을 관찰하여 반응 선택성과 메커니즘의 관계를 규명하고자 한다.

    • 자주묻는질문의 답변을 확인해 주세요

      해피캠퍼스 FAQ 더보기

      꼭 알아주세요

      • 자료의 정보 및 내용의 진실성에 대하여 해피캠퍼스는 보증하지 않으며, 해당 정보 및 게시물 저작권과 기타 법적 책임은 자료 등록자에게 있습니다.
        자료 및 게시물 내용의 불법적 이용, 무단 전재∙배포는 금지되어 있습니다.
        저작권침해, 명예훼손 등 분쟁 요소 발견 시 고객센터의 저작권침해 신고센터를 이용해 주시기 바랍니다.
      • 해피캠퍼스는 구매자와 판매자 모두가 만족하는 서비스가 되도록 노력하고 있으며, 아래의 4가지 자료환불 조건을 꼭 확인해주시기 바랍니다.
        파일오류 중복자료 저작권 없음 설명과 실제 내용 불일치
        파일의 다운로드가 제대로 되지 않거나 파일형식에 맞는 프로그램으로 정상 작동하지 않는 경우 다른 자료와 70% 이상 내용이 일치하는 경우 (중복임을 확인할 수 있는 근거 필요함) 인터넷의 다른 사이트, 연구기관, 학교, 서적 등의 자료를 도용한 경우 자료의 설명과 실제 자료의 내용이 일치하지 않는 경우
    • 정가
      4,000원
      판매자스토어판매자스토어 자료문의자료문의 링크복사 링크복사
      • 지식판매자
        difje G
      • 페이지
        16 페이지 어도비 PDF
      • 최초등록일
        2024.08.22
      • 최종저작일
        2024.05
    문서 초안을 생성해주는 EasyAI
    안녕하세요 해피캠퍼스의 20년의 운영 노하우를 이용하여 당신만의 초안을 만들어주는 EasyAI 입니다.
    저는 아래와 같이 작업을 도와드립니다.
    - 주제만 입력하면 AI가 방대한 정보를 재가공하여, 최적의 목차와 내용을 자동으로 만들어 드립니다.
    - 장문의 콘텐츠를 쉽고 빠르게 작성해 드립니다.
    - 스토어에서 무료 이용권를 계정별로 1회 발급 받을 수 있습니다. 지금 바로 체험해 보세요!
    이런 주제들을 입력해 보세요.
    - 유아에게 적합한 문학작품의 기준과 특성
    - 한국인의 가치관 중에서 정신적 가치관을 이루는 것들을 문화적 문법으로 정리하고, 현대한국사회에서 일어나는 사건과 사고를 비교하여 자신의 의견으로 기술하세요
    - 작별인사 독후감
    “EasyAI 가 작성한 문서 초안은 완벽하지 않을 수 있습니다"
    EasyAI 이동하기
    해캠 AI 챗봇과 대화하기
    챗봇으로 간편하게 상담해보세요.
    2025년 12월 31일 수요일
    AI 챗봇
    안녕하세요. 해피캠퍼스 AI 챗봇입니다. 무엇이 궁금하신가요?
    3:18 오후