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"유기화학실험 Nitration"에 대한 내용입니다.목차
1. subject2. date
3. name
4. principle and object
5. material(apparatus, instruments, reagents)
6. procedure and observation
7. result
8. reference
본문내용
-treatment of methyl benzoate with HNO3, H2SO4 : methyl benzoate에 HNO3, H2SO4를 친전자성 방향족 치환반응(Electrophilic Aromatic Substitution)시키면 methyl 3-nitrobenzoate를 생성할 수 있다. 먼저, HNO3, H2SO4가 반응의 친전자체인 NO2+(Nitronium cation; the reactivity is very high because it is very unstable and has electronegative positive charged nitrogen)를 생성하는데, 전부 액체상인 반응물들로부터 고체상인 product를 얻은 뒤에는 purification을 위해 recrystallization하고(액체상이 아니므로 Column Chromatography 대신 recrystallization한다.) product structure을 알기 위해 melting point나 NMR을 하면 된다.-NMR: spectra를 분석해 Proton을 확인할 수 있는 기계이다. 과정은 다음과 같다.
○,1 NMR 기기 찍기
○,2 spectra 얻기
○,3 이미 알려진 NMR spectrum과 겹쳐지는지 확인하기
-reaction of methyl benzoate: methyl benzoate를 반응물로 하여 다음과 같은 생성물을 얻을 수 있다.
-resonance form of protonation including ortho/meta/para Regiochemistry: Figure 2.의 ○,2번은 옥텟을 만족하여 기여도가 높고, ○,3번의 탄소양이온 6전자 때문에 기여도가 낮지만 EWG ability를 설명하기 위해 공명구조 그림에 포함시켰다. ○,2번의 작용기는 protonation되어 strong EWG인데, ipso carbon positive charge를 destabilization시키므로 ipso carbon(electron withdrawing substituent에 바로 붙은 carbon) positive charge되는 Regiochemistry는 피해야 한다.
참고 자료
John Mcmurry. Organic Chemistry. 9th edition. Cengage Learning. 2016.The handout prepared by chemistry department. nitration
생화학분자생물학회. 생화학백과. 극성. https://www.ksbmb.or.kr/html/
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산업재해예방 안전보건공단. MSDS. Acetone. https://msds.kosha.or.kr/MSDSInfo/AIViewer/msdsAireport/msds_summary/A_OnePage.jsp
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David A. Widdowson. the chemistry of nitrogen compounds. https://www.ch.ic.ac.uk/widdowson/teach_files/nitrogen/dw1.html
