有機化學(一)

本課程介紹有機分子的基本性質及反應。課程中將探討有機化合物的結構、形狀以及其對不同試劑的反應性，並介紹如何利用分子軌道的相互作用來理解有機反應的一般機制。本課程系統性地著重反應中的通用原理以及三維分子結構對反應性的影響。此外，課程將介紹用於鑑定有機分子結構的重要分析技術，例如質譜、核磁共振和紅外光譜。 課程目標： o 理解用來描述有機分子形狀與鍵結的方法。 o 辨識並解釋各類飽和與不飽和有機化合物的結構與反應性；這些化合物包括但不限於烷類、烯類、炔類、羰基化合物以及芳香族化合物。 o 透過分析反應物的結構和反應條件，預測反應的結果。 o 基於已知的反應途徑及其反應機制，推測未知但類似反應的可能機制。 o 連結分子的立體三維結構與其反應性。 o 根據課程中所涵蓋的反應，設計簡單分子的合成路徑。 This course introduces students to the fundamental principles governing the chemical behavior of organic molecules. It explores the structure, shape, and reactivity of organic compounds toward different classes of reagents, focusing on a mechanistic understanding of key functional group transformations, in terms of orbital interactions and electron flow. The course emphasizes general principles that reveal systematic patterns of reactivity and the role of three-dimensional molecular structure in influencing organic reactions. Additionally, students will be introduced to key analytical techniques, such as MS, NMR, and IR, for determining organic structures. Course Objective: • Demonstrate an understanding of the methods and conventions used to describe the shapes and bonding in organic molecules. • Identify and explain the general structure and reactivity of a variety of saturated and unsaturated organic compounds, including but not limited to alkanes, alkenes, alkynes, carbonyls, and aromatic compounds. • Predict the outcome of reactions by analyzing the substrate structure and reaction conditions. • Infer likely mechanisms for unfamiliar but related reactions using mechanistic reasoning and known reaction pathways. • Correlate molecular structure and stereochemistry with reactivity across a broad range of organic reactions. • Design synthetic routes for simple molecules based on reactions covered in the syllabus.

普通化學 / General Chemistry

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• 作業 (10%)：每單元指定習題，手寫紙本繳交。習題內容與小考、期中期末考相關，請務必動手練習。依繳交狀況評分。 • 隨堂小考(15%)：全學期 5 次，授課教師於考試前一次上課時預告考試日期與範圍。每次3-4 題，約20分鐘。取最高 4 次計分，缺考該次以 0 分計，不另安排補考。 • 期中考 (30%)，涵蓋約學期前半內容，暫定 11月12日舉行。 • 期末考 (45%)，範圍涵蓋全學期，暫定 12月24日舉行。 缺考處理：檢附正當證明者，期中缺考則權重轉移至期末考（期末考調整為 75%），期末缺考則另安排補考；無正當證明者以 0 分計。正當證明指醫院診斷書、公家機關公文、直系親屬過世證明或學校核准之公假證明。 • Homework (10%): Assigned problems from each unit, submitted as handwritten hard copies. The problems relate directly to quizzes, midterm, and final exam questions, so please work through them carefully. Graded on submission. • In-class quizzes (15%): Five quizzes over the semester. The date and scope of each quiz will be announced during the previous class. Each quiz consists of 3-4 questions and takes about 20 minutes. The best four scores count toward the final grade; a missed quiz counts as zero, and no makeup will be arranged. • Midterm exam (30%): Covers approximately the first half of the semester. Tentatively scheduled for November 12. • Final exam (45%): Covers material from the entire semester. Tentatively scheduled for December 24. Missed exams: With valid documentation, the weight of a missed midterm will be transferred to the final exam (making the final worth 75%); a makeup will be arranged for a missed final. Missed exams without valid documentation will be graded as zero. Valid documentation includes a hospital medical certificate, official government document, immediate family death certificate, or university-approved official leave.

• Semester 1: Structure, Arrows, π Reactivity, and Structure Determination

  1: Molecular Architecture in 3D (McMurry Chapters: 1-4) - Draw valid Lewis structures and line-bond structures for simple organic molecules. - Calculate formal charges for atoms within organic molecules. - Identify the hybridization state (sp3, sp2, sp) of carbon and heteroatoms. - Evaluate the electronegativity of atoms to identify polar covalent bonds and molecular dipoles. - Analyze Newman projections to predict the most stable conformation of open-chain alkanes. - Identify axial and equatorial positions on cyclohexane chairs and predict the lowest-energy ring-flip conformation. 2: Stereochemistry and Chirality (McMurry Chapters: 5) - Identify stereocenters and assign absolute configurations (R or S). - Differentiate between enantiomers, diastereomers, and meso compounds. - Predict the stereochemical relationships between molecules presented in different orientations. 3: The Basic Grammar of Reactivity (or Curved Arrows, Resonance, and Acid-Base Chemistry, McMurry Chapters: 2, 6) - Master the electron-pushing formalism by tracking electrons with curved arrows to construct resonance forms. - Rank resonance contributors based on complete octets, charge separation, and electronegativity. - Predict the direction of acid-base equilibria using qualitative structural features and quantitative pKa values - Identify nucleophilic (electron-rich) and electrophilic (electron-poor) sites on a molecule using resonance. 4: Electron Flow Patterns in Carbonyls (π* Bonds as Electrophiles I, McMurry Chapters: 19) - Draw mechanisms for nucleophilic additions to carbonyl π bonds. - Draw mechanisms for the reversible formation of acetals from ketones/aldehydes and alcohols. - Predict the products of addition of Grignard reagents, organolithiums, and hydride reducing agents to carbonyls. - Predict the stereochemical outcomes when nucleophiles add to planar sp2 hybridized electrophiles. 5: Electron Flow Patterns in Alkenes & Alkynes (π Bonds as Nucleophiles I, McMurry Chapters: 7, 9) - Predict the major regioisomer formed during electrophilic addition to alkenes and alkynes - Evaluate relative carbocation stability (3° > 2° > 1° > methyl) via hyperconjugation and inductive effects. - Predict spontaneous hydride or alkyl shifts that convert less stable carbocations into more stable ones. 6: Complex Additions to π Bonds (π Bonds as Nucleophiles II, McMurry Chapters: 7, 8) - Draw mechanisms for the reactions of π bonds with halogens via the halonium ion intermediate. - Differentiate between reagents that result in syn versus anti addition across a π bond. - Draw mechanisms for the epoxidation by peroxyacids. - Understand the principles that convert less stable intermediates into more stable ones in rearrangement reactions. 7: Conjugated Systems and Aromaticity (McMurry Chapters: 14, 15) - Use molecular orbital theory to explain the increased stability and altered bond lengths of conjugated dienes. - Apply Hückel's rule (4n+2 π electrons) to classify rings as aromatic, anti-aromatic, or non-aromatic. - Predict whether a heteroatom's lone pair participates in a conjugated π system. 8: Electrophilic Reactivity of Aromatic Rings (π Bonds as Nucleophiles III, McMurry Chapters: 16) - Draw the general electron flow for electrophilic aromatic substitution, explicitly showing the resonance stabilization of the intermediate and recognizing its mechanistic similarity to alkene addition. - Predict the (de)activate and directing effects (ortho/para vs. meta) of electron-donating and electron-withdrawing substituents. - Design multi-step syntheses of polysubstituted benzenes, demonstrating the critical importance of reaction order. 9: Single-Electron Movements and Polymer Chemistry (McMurry Chapters: 6, 8, 10, 31) - Track single-electron flow using fishhook arrows through the initiation, propagation, and termination steps of a radical chain reaction. - Predict the regioselectivity of free-radical halogenation based on the stability of carbon radical intermediates. - Apply the radical propagation cycle to explain the industrial synthesis of chain-growth polymers. 10: Structure Determination (Intro to Mass Spectrometry, IR Spectroscopy & Nuclear Magnetic Resonance, McMurry Chapters: 12, 13) - Interpret Mass Spectrometry (MS) data to deduce the molecular weight, formula, and presence of isotopes in organic molecules. - Identify key functional groups (e.g., OH, C=O, C≡N) using characteristic Infrared (IR) frequencies. - Interpret 1H and 13C NMR spectra using chemical shift, integration, and spin-spin splitting (2nI+1 rule) to determine structural fragments. - Deduce simple organic structures purely from a combination of MS, IR, and NMR data.

McMurry, J. E. Organic Chemistry, 10th ed. (OpenStax, 2023). Freely available online at https://openstax.org/details/books/organic-chemistry. Licensed under CC BY-NC-SA.

地點

科學二館 R517 SB R517

時間

週一 15:30-16:30；或 email 另約時間。 Mondays 15:30-16:30; other times available by appointment via email.

聯絡方式

Email: yilin.wu@nycu.edu.tw