Organizing Organic Chemistry Basics E-Book

Jeongbin Park

• Herausgeber: 이즈그리민(izgrimean)
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 136

Veröffentlichungsjahr: 2024

Beschreibung

This book describes fundamental concepts for studying organic chemistry. It covers chemical concepts that are commonly applied across the entire spectrum of organic chemistry, from general chemistry principles like chemical bonding and orbitals to physical properties, nomenclature, and stereochemistry. Drawing on the collective wisdom of the masses, it was possible to complete the category of organic chemistry, and it is believed that this created category is the most efficient way to learn organic chemistry concepts.

I opened a blog called “Jeongbin’s Study Room” to collect knowledge from many people. The enthusiasm for organic chemistry is still strong today, but a few years ago, it was significant, as organic chemistry was essential for various exams. Since studying organic chemistry in elementary, middle, and high school was rare, I anticipated a significant academic demand for organic chemistry. Therefore, since 2018, I have been sharing articles on organic chemistry on “Jeongbin’s Study Room” and communicating, correcting, and discussing with people. I have had many discussions online with medical professionals, pharmacists, lawyers, current teachers, and professors, among others. Now, as we welcome the new year 2024, I declare that the compilation of organic chemistry knowledge through collective intelligence is complete and I am publishing this book. I hope that this book can lower the barrier of organic chemistry as a field of study.

Leseprobe

Creative Commons

Organizing Organic Chemistry Basics

Author ｜ Jeongbin Park

Editor ｜ EUNJOLEE, Jeongbin Park

Cover Design ｜ EUNJOLEE

Published by ｜ 이즈그리민(izgrimean)

Publisher ｜ EUNJOLEE

Date of Publication ｜ June 17, 2024

Publisher Registration ｜ May 24, 2023, No. 2023-000052

EMAIL ｜ [email protected]

First Edition eBook Published ｜ June 17, 2024

ISBN ｜ 979-11-987080-3-8(95430)

© 2024, 이즈그리민(izgrimean). All rights reserved. Reproduction or distribution of this work, in whole or in part, without explicit permission from 이즈그리민(izgrimean) is prohibited by law.

For reuse of any part of this book, permission must be obtained from both the copyright holder and 이즈그리민(izgrimean).

▶The cover, logos, text, and illustrations of this content utilize the following fonts.

- 'Cambria Math' and 'Arial', provided by Microsoft

- '속초바다 돋움', provided by 속초시

- '나눔고딕' and '나눔바른고딕', provided by 네이버(NAVER)

Some of the fonts used in the images of this book have not been verified, and should any copyright holder request, the content will be modified accordingly.

Getting Started

Comments from Jeongbin Park

I opened a blog called “Jeongbin’s Study Room” to collect knowledge from many people. The enthusiasm for organic chemistry is still strong today, but a few years ago, it was significant, as organic chemistry was essential for various exams. Since studying organic chemistry in elementary, middle, and high school was rare, I anticipated a significant academic demand for organic chemistry. Therefore, since 2018, I have been sharing articles on organic chemistry on “Jeongbin’s Study Room” and communicating, correcting, and discussing with people. I have had many discussions online with medical professionals, pharmacists, lawyers, current teachers, and professors, among others. Now, as we welcome the new year 2024, I declare that the compilation of organic chemistry knowledge through collective intelligence is complete and I am publishing this book. I hope that this book can lower the barrier of organic chemistry as a field of study.

◎ If you send the purchase receipt of the book to [email protected], we will provide you with additional lecture materials and problem sets.

Ch. 1: Basics of Chemistry

Ch. 1: Basics of Chemistry

1. What is Chemistry?

2. Grammar of Chemical Formulas

3. Chemical Reaction Equations

1. What is Chemistry?

⑴ Chemistry: The study of matter

① Composition, properties, structure of matter

② Changes in matter

⑵ Phases of Matter

① Solid

○ Has a definite shape and fixed volume.

② Liquid

○ More irregular than a solid.

○ Because its movements are relatively free, it has flowing properties.

○ It doesn't have a fixed shape and takes the shape of its container, though its volume remains constant.

③ Gas

○ More disordered than liquids.

○ Molecules are far apart, leading to negligible molecular interactions.

○ Much lighter compared to solids or liquids of the same volume.

○ Compression changes the shape and volume.

○ It occupies space.

⑶ Classification of Matter

① Class 1: Pure Substances: Classified into elements and compounds.

○ Class 1-1: Elements

○ Substances composed of only one type of atom.

○ Examples: Copper (Cu), Nitrogen (N2), Iron (Fe), Diamond (C), Aluminum (Al)

○ Class 1-2: Compounds

○ Substances composed of two or more different elements in a fixed ratio.

○ Examples: Carbon Dioxide (CO2), Copper Sulfate (CuSO4), Water (H2O)

② Class 2. Mixtures: Classified into homogeneous and heterogeneous mixtures

○ Class 2-1: Homogeneous Mixtures

○ Also called solutions.

○ Mixtures where multiple pure substances are uniformly distributed, so the composition is the same throughout.

○ Examples: Air, Sugar Solution, Saltwater, Alloys

○ Class 2-2: Heterogeneous Mixtures

○ Mixtures where multiple pure substances are not uniformly distributed, so the composition varies in different parts.

○ Examples: Muddy Water, Milk, Granite, Blood, Smoke

⑷ Properties of Matter

① Physical Properties

○ Changes in phase or form of matter without altering its chemical composition.

○ Examples: Color, Melting Point, Boiling Point, Density, Solubility, etc.

② Chemical Properties

○ Transformation of a substance into new substances through chemical reactions.

2. Grammar of Chemical Formulas

⑴ Atoms, Elements, Molecules, Ions

① Atom: Fundamental unit in most chemical reactions. Units smaller than atoms were observed after the 1900s.

② Element: Collection of atoms with similar characteristics.

③ Molecule: Functional unit composed of bonded atoms.

④ Ion: Atom with a charge due to gaining or losing electrons.

⑤ Representation of Atoms or Ions

○ a: Number of protons + Number of neutrons

○ b: Number of protons

○ c: Indicates the charge of X. -2, -, +, +2, etc.

○ d: Indicates the number of X.

⑥ Isotope: Elements with the same atomic number but different neutron numbers, thus having different masses.

⑵ Mole

① Mole: Unit for counting atoms or molecules.

② Avogadro's Number (NA): Number of atoms in one mole. That is, the number of atoms in 12.00 g of carbon-12 (12C).

③ Gas volume of 1 mole is constant for all gases, at STP (0 ℃, 1 atm). That is, it's 22.4 L.

○ Derived from the ideal gas law.

④ Humans are composed of around 10,000 moles.

⑶ Chemical Formulas, Chemical Reaction Equations, and Reaction Yield

① Chemical Formula: Representation of a substance.

○ Empirical Formula: Simplest integer ratio of atoms.

○ Example: Empirical formula of glucose is CH2O.

○ Molecular Formula: Actual number of atoms in a molecule.

○ Example: Molecular formula of glucose is C6H12O6.

○ Determining Chemical Formula by Experiments

○ Step 1: Mass percentage composition analysis

○ Step 2: Empirical formula determination

○ Step 3: Molecular formula determination by using mass spectrometry

② Structural Formula

○ Sequence

○ Basic Structural Formulas

○ 3D Structural Formulas

⑷ Stoichiometry

① Mass

○ Molecular Weight: Relative mass of one molecule. Sum of atomic weights of atoms in the molecule (no units).

○ Experimental Weight: Sum of atomic weights in the experimental formula.

○ Average Atomic Weight: Weighted average considering the isotopic distribution. Calculation of carbon's average atomic weight is shown below.

② Concentration

○ Molar Concentration: Moles of solute (mol) ÷ Volume of solution (L)

○ Molal Concentration: Moles of solute (mol) ÷ Mass of solvent (kg)

○ Related to boiling point increase, freezing point decrease, etc.

○ Mole Fraction: Moles of a specific substance (mol) ÷ Total moles in the mixture (mol)

○ Dimensionless quantity.

○ Mass Percent (%): Mass of solute (kg) ÷ Mass of solution (kg) × 100 (%)

○ ppm (parts per million), ppb (parts per billion)

○ ppmv (parts per million by volume), ppbv (parts per billion by volume)

③ Gram Equivalent

○ The mass or molecular weight divided by the equivalent.

○ That is, it represents the number of grams corresponding to 1 mole equivalent.

3. Chemical Reaction Equations

⑴ Chemical Reaction Equation: Representation of chemical reactions using chemical formulas.

① Reactant

② Product

③ Reagent: Chemical substance available for use in the laboratory.

④ Spectator Ion: Ions indicated in the equation that do not participate in the reaction but are present.

○ The equation excluding spectator ions is called the net ionic equation.

⑤ Method for writing chemical reaction equations

○ Step 1: Represent reactants and products with chemical formulas.

○ Step 2: Skeletal equation: Write down which chemical species react.

○ Step 3: Balanced chemical equation: Calculate coefficients in the skeletal equation.

○ Step 4: Detailed chemical equation: Include states of each chemical species (e.g., g , l, s, aq) and conditions (e.g., Δ, hν).

○ Gas state: (g)

○ Liquid state: (l)

○ Solid state: (s)

○ Aqueous solution state: (aq)

⑵ Laws of Chemical Reaction Equations

① Law of Conservation of Mass: Number of atoms must be conserved for all atoms, except in nuclear reactions.

② Law of Conservation of Charge: Sum of charges in reactants equals sum of charges in products.

③ Law of Definite Proportions: Elements combine in fixed ratios.

④ Law of Multiple Proportions: Different elements combine in integer ratios to a fixed mass of one element.

○ Except when two elements form more than one compound.

⑶ Coefficient Calculation in Chemical Reaction Equations

① For redox reactions, the reciprocal ratio of oxidation number change between oxidized and reduced species gives the coefficient ratio.

○ Usually, the redox reaction involves determining the coefficients for species by considering the changes of oxidation numbers, then balancing the coefficients of H2O and H+.

② Example

○ C6H14 + O2 → CO2 + H2O

○ 1C6H14 + O2 → CO2 + H2O

○ 1C6H14 + O2 → 6CO2 + H2O (∵ C)

○ 1C6H14 + O2 → 6CO2 + 7H2O (∵ H)

○ 1C6H14 + 19/2O2 → 6CO2 + 7H2O (∵ O)

○ 2C6H14 + 19O2 → 12CO2 + 14H2O

⑷ Limiting Reactant

① Substance consumed entirely in a reaction.

② Amount of products formed is proportional to the amount of limiting reactant.

① Reactions are not always complete due to chemical equilibrium and reverse reactions.

⑹ Classification of Reactions

① All reactions involve electron movement, breaking and forming bonds.

② Reactions with electron movement and change in oxidation number: Redox Reactions

③ Reactions with electron movement but no change in oxidation number: Acid-Base Reactions.

○ Further categorized into precipitation reactions and non-precipitation reactions.

Ch. 2: Classical Atomic Theory

Ch 2: Classical Atomic Theory

1. History of Atomic Models

2. Classical Atomic Model

3. Classical Molecular Model

4. Drawing Molecular Structures

5. Formal Charge

1. History of Atomic Models

⑴ 1st. Democritus

① Particle Theory (5th century BC): Proposed that all matter is composed of indivisible particles.

② Atom: Derived from the Greek word "atomos," meaning indivisible.

③ Refuted by Plato and Aristotle.

⑵ 2nd. Dalton

① Atomic Theory: Accurate definition of the atom (1808).

② Hypothesis 1: All matter consists of indivisible particles.

○ Exception: Atoms can be divided into a nucleus and electrons.

○ Exception: Atoms can be further broken down by nuclear fission.

③ Hypothesis 2: Same types of atoms have the same size and properties; different types have different sizes and masses.

○ Exception: Isotopes

④ Hypothesis 3: Atoms are neither created nor destroyed and do not change into different kinds.

○ Exception: Nuclear reactions

⑤ Hypothesis 4: Different atoms combine in fixed ratios to form new substances.

⑶ 3rd. Thomson

Figure 1. Thomson's Cathode Ray Experiment

① Thomson's Cathode Ray Experiment: In 1897, using a vacuum discharge tube, it was discovered that the flow of cathode rays was the flow of particles known as electrons.

② Rejection of Dalton's Atomic Theory: Atoms can be divided into negatively charged electrons and positively charged protons.

③ Proposal of the Plum Pudding Model

○ Overall structure resembles a positively charged sphere.

○ Electrons with equal negative charges are scattered throughout.

○ Significance: Partial explanation of atomic electric properties.

○ Limitation: Challenged by Rutherford's alpha particle scattering experiment.

⑷ 4th. Millikan

① Millikan Experiment: He determined the quantized charge of electrons.

② He calculated the mass of electrons from their charge.

⑸ 5th. Rutherford

Figure 2. Rutherford's Experiment

① Purpose of Rutherford's Experiment: To verify Thomson's Plum Pudding Model

② Experimental Process (1911)

○ Created a thin gold foil with a thickness of 1/20,000 cm.

○ Fired alpha particles from radioactive sources at the gold foil.

○ Placed a zinc sulfide screen behind the foil to detect small flashes produced by alpha particles hitting.

③ Expected Results: According to Thomson's model, there should be no deflection of alpha particles.

④ Experimental Results

Figure 3. Model of α-Particle Scattering

○ A few alpha particles scattered in unexpected directions upon impact, that is the particles failed to pass through the foil.

○ About 1 out of 8,000 alpha particles scattered at 180° (backward scattering).

⑤ Interpretation of Results

Figure 4. Rutherford's Atomic Model

○ Alpha particles not passing through the 1/20,000 cm gold foil ≒ Bullets not passing through thin tissue paper

○ Presence of a heavy, dense structure with significant positive charge: It leads to the introduction of atomic nucleus.

○ In other words, alpha particles scatter because their mass is smaller than the gold foil's atomic nucleus.

○ Solar system model proposed (1910): Atoms with a central nucleus around which electrons orbit.

⑥ Limitations 1: Stability of Atoms

○ Cannot explain stability of electrons in circular orbits.

○ That is, accelerating or rotating electrons emit light energy and eventually fall into the nucleus.

⑦ Limitations 2: Hydrogen Gas Line Spectrum: According to the solar system model, a continuous spectrum should be observed.

⑹ 6th. Bohr Atomic Model

⑺ 7th. Discovery of Protons and Neutrons

① In 1896, E. Goldstein discovered positive rays.

② 1914, Rutherford Experiment: Suggested the existence of protons.

③ In 1932, J. Chadwick discovered particles (neutrons) in the atomic nucleus without a charge.

○ Note that Chadwick was a student of Rutherford.

2. Classical Atomic Model

⑴ Atom

① Atomic Theory: Introduced by Dalton.

○ Etymology: Indivisible (a-) particles (tom)

○ In ions, number of protons ≠ number of electrons.

⑥ Atomic Symbol

○ A: Atomic Mass

○ B: Atomic Number

○ C: Charge

○ D: Number of atoms

⑦ Isotopes

○ Elements with the same atomic number but different mass numbers: Difference in number of neutrons.

○ All elements have two or more isotopes.

⑵ Periodicity

① Periodic Table: Related to electrons, protons, neutrons, atomic mass.

Figure 5. Periodic Table

○ Period: Number of electron shells. 1st period, 2nd period, ···

○ Group: Set of atoms with the same number of outermost electrons.

○ Metal: Group of atoms with a strong tendency to donate electrons.

○ Nonmetal: Group of atoms with a strong tendency to gain electrons.

○ Metalloid: Possesses properties of both metals and nonmetals. 7 elements (B, Si, Ge, As, Sb, Te, Po)

○ Main Group Elements: s-block, p-block

○ Transition Elements: d-block

○ Lanthanides: f-block

○ Common oxidation state is +3.

○ Typically form coordination compounds with coordination numbers greater than 6.

○ React with acids to release hydrogen

○ Form stable complexes using oxygen as a ligand.

○ Actinides: f-block

② Periodic Behavior of Atoms: Driven by forces between nucleus and electrons (related to the number of protons in the nucleus and nuclear-electron distance) and electron-electron repulsion.

③ Atomic Radius

○ Atomic size cannot be precisely defined due to the probabilistic nature of electron clouds.

○ Definition 1: Half the distance between the nuclei of two atoms bonded together, excluding noble gases.

○ Reasonable to define the atomic radii of O2 and N2 as half the distance between their nuclei.

○ Unreasonable to define the atomic radius of HF using this approach.

○ Definition 1: concept can also be applied to metallic bonding.

○ Definition 2: It defines atomic size using Van der Waals radius for noble gases.

○ Ion Radius Definition: It considers distance and weighting between ions in ionic bonding.

○ Trend 1: Atomic radius decreases with increasing atomic number in the same period.

○ Trend 2: Atomic radius increases with increasing number of electron shells in the same group.

④ Effective Nuclear Charge

○ The positive charge felt by an electron. A measure of the attractive force considering electron repulsion.

○ Comparison of effective nuclear charge within an atom: Inner orbitals experience greater effective nuclear charge.

○ Comparison of effective nuclear charge of outermost electrons between atoms

○ Within the same period, atomic radius decreases as atomic number increases, leading to an increase in effective nuclear charge.

○ Within the same group, effective nuclear charge slightly increases as the number of electron shells increases. Opposite trend to ionization energy.

○ Comparison of effective nuclear charge of specific orbitals between atoms

○ With an increase in atomic number, the effective nuclear charge of a specific orbital mentioned in the problem increases.

○ Comparison of the nuclear repulsive force between atoms

○ As the number of electron shells increases, the nuclear repulsive force becomes stronger.

○ Reason: Because the influence of the atomic number is greater than the shielding effect of the electrons.

○ Slater's Rule: A formula for effective nuclear charge.

○ If the principal quantum number of valence electrons in the outermost shell is denoted as n