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Video descriptions |
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Document
descriptions |
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Trigonometry: “Sine, cosine, and the unit
circle”. How
to use the unit circle to remember values of sine and cosine for certain
reference angles. |
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Calculus: “Percentage growth
rates. Elasticity of demand”. Calculating the
percentage growth rate; calculating the percentage growth rate using a
logarithmic derivative. Elasticity of demand; relation between elasticity of
demand and revenue |
Problems discussed in the videos |
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Calculus: “The chain rule for antidifferentiation”. The chain rule for antidifferentiation, also known as the inverse chain rule |
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Calculus: “First-semester calculus
final exam review”. First-semester calculus final exam review session. Evaluating a limit. Quotient Rule for derivatives. Chain rule. Implicit differentiation.
A 57th-order derivative. L'Hôpital's rule. Minimizing a function (First Derivative and Second Derivative
Tests). |
Problems discussed in the videos |
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Physics: how to solve kinematics problems about general one-dimensional motion |
Kinematics equations and method |
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Physics: “More on one-dimensional
kinematics”. One-dimensional kinematics. Unit conversion; metric prefixes. Time, position, displacement, velocity, acceleration. Vectors vs. scalars; vector arrows. Using the kinematics
equations—a problem. How to do problems with zero
acceleration (i.e., constant velocity). A two-object kinematics
problem |
Kinematics equations and method |
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Problems discussed in videos |
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Physics: how to solve kinematics problems about one-dimensional projectile motion |
Kinematics equations and method |
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Physics: trigonometry--how to break an overall vector into components, and how to determine an overall vector from its components |
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Physics: how to solve kinematics problems about general two-dimensional motion |
Kinematics equations and method |
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Physics:
“Two-dimensional projectile motion”. Kinematics
of general two-dimensional motion. Two-dimensional projectile motion |
Problems discussed in the videos |
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Kinematics equations and method |
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Physics: “Using |
Mechanics |
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Physics: “Work. Conservation of energy”. Kinetic energy. Work and the work-energy theorem. Conservative and nonconservative forces. Gravitational potential energy; spring potential energy. Total mechanical energy. Net Wnc = ΔE. Conservation of energy problems. A problem in which mechanical energy is not conserved. |
Work and energy |
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Physics: “Conservation of energy & momentum problem”. A problem involving conservation of energy, conservation of momentum, and elastic, inelastic, and totally inelastic collisions |
Problem discussed in the videos |
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Work and energy |
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Momentum |
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Physics: “Rotational kinematics
and torque”. Rotational kinematics. Angular displacement (Δθ); angular velocity
(ω); angular acceleration (α). Torque |
Problem discussed in the videos |
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Rotation |
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Physics: “Torque”. Torque and rotational motion. |
Rotation |
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Physics: “Conservation of energy with rotation”. Conservation of energy applied to rotational motion. |
Work and energy |
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Rotation |
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Physics: “Energy, momentum,
torque”. Conservation of momentum, conservation of energy, |
Work and energy |
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Rotation |
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Physics: “Statics”. Translational and rotational equilibrium |
Rotation |
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Physics: “Rotational statics and dynamics problems” |
Problems discussed in the videos |
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Rotation |
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Physics: “Waves and oscillations”. Period, frequency, angular frequency, wavelength, amplitude. Simple harmonic motion; springs; conservation of energy. |
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Physics: “Wave motion”. Transverse vs. longitudinal waves. Wave graphs. Velocity (v) versus frequency (f); frequency (f) versus angular frequency (ω) |
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Physics: “Fluids—pressure and buoyant force”. Pressure; gauge pressure. Density. Buoyant force |
Problems discussed in videos |
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Physics: “A buoyant-force problem” |
Problem discussed in the videos |
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Physics: “Ideal gas law. Heat, temperature, phase”. Pressure; gauge pressure. Ideal gas law. Heat, temperature, and phase changes; specific heat and heat of transformation |
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Physics: “First Law of Thermodynamics”. First Law of Thermodynamics; internal energy, heat, work. P-V curves. Special processes: isobaric (constant pressure); isochoric (constant volume); cyclic; isothermal (constant temperature); adiabatic (zero heat exchange). State functions |
First and Second Laws of Thermodynamics |
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Physics: “Thermodynamic processes”. First Law of Thermodynamics and thermodynamic
processes. Isobaric,
isochoric (constant volume), isothermal, and adiabatic processes. Molar specific heat (C). A problem involving thermodynamic
processes |
First and Second Laws of Thermodynamics |
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Problem discussed in the videos |
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Physics: “Entropy and Second Law of Thermodynamics”. Entropy and the Second Law of Thermodynamics. Entropy as a state function. General formulas for calculating entropy change. How to calculate entropy change for phase change or temperature change problems. The Second Law of Thermodynamics; reversible vs. irreversible processes. Entropy change in isothermal processes, adiabatic processes, and adiabatic free expansions |
First and Second Laws of Thermodynamics |
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Problem discussed in the videos |
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Physics: “Electric field and electric force”. Electric charge. Electric force; Coulomb’s law. Net electric force from a charge distribution; the superposition principle. Electric field. Coulomb’s law for electric field. Net electric field from a charge distribution; the superposition principle for electric field |
Electric field and force; electric potential and potential energy |
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Physics: “Coulomb’s law” |
Problem discussed in the videos |
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Physics: “Electric field lines and Gauss's law”. Electric
field lines. Electric flux. Gauss's law. Using Gauss's law to determine the electric
field from charge distributions with spherical symmetry and plane symmetry |
Electric field and force; electric potential and potential energy |
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Problem discussed in the videos |
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Physics: “Electric potential and potential energy”. Electric
potential energy. Electric potential. Electric
potential difference (“voltage”) and change in electric potential
energy |
Electric field and force; electric potential and potential energy |
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Physics: “Electric circuits.
Resistors”. Physics: Electric circuits. Voltage
sources and drops. Current. Current and voltage for circuit elements in series or parallel.
Kirchhoff's loop law; Kirchhoff’s node law. Resistance. Ohm's law. Equivalent
resistance for resistors in series or parallel |
Electric field and force; electric potential and potential energy |
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Physics: “A problem involving electric current” |
Problem discussed in the video |
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Physics: “Adding resistors to electric circuits”. Adding or dropping resistors to electric circuits, in series or parallel--effects on equivalent resistance, current, voltage, and power. |
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Physics: “Magnetic field and force. Right-hand rules”.
Right-hand rule
for the direction of the magnetic force on a moving charge; right-hand rule
for the direction of the magnetic force on a current-carrying wire. Magnitude of the magnetic force on a moving charge; magnitude of
the magnetic force on a current-carrying wire. Right-hand
rule for the direction of the magnetic field from a long straight wire.
The magnitude of the magnetic field from a long straight wire |
Electric field and force; electric potential and potential
energy |
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Magnetic field and force |
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Physics: “Net magnetic field from current-carrying wires”. Sources of electric and magnetic fields. Net magnetic field from multiple current-carrying wires. Magnetic force on a moving charge. Right-hand rules. Circular trajectory of a charged particle in a magnetic field |
Problem discussed in the videos |
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Electric field and force; electric potential and potential energy |
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Magnetic field and force |
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Physics: “Balancing electric and magnetic forces”. Selecting particles of a particular velocity by adjusting electric and magnetic fields; using the right-hand rule for magnetic force. |
Problem discussed in the videos |
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Physics: “Capacitors and inductors; RC and RL circuits”. Behavior of voltage, charge and current over time in electric circuits with capactors; charging and discharging RC circuits; the time constant. Behavior of voltage and current over time in circuits with inductors; RL circuit with battery, and with battery removed |
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Physics: “Alternating current; RLC circuits”. Alternating current (AC) circuits. Root-mean-square (rms) voltage and current. Resistors, capacitors, and inductors in AC circuits; phasor diagrams for resistors, capacitors, and inductors. Power in AC circuits. Reactance (X); impedance (Z). Resonant frequency. An RLC circuit problem |
Problems discussed in videos |
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Physics: “Optics of lenses and
mirrors”. Introduction to the optics of lenses and mirrors. Concave, convex, converging, diverging; real, virtual; upright,
inverted, magnified, shrunk. Sign conventions for focal length, image
distance, object distance, magnification. The lens/mirror
equation; the magnification equation. Introduction to ray tracing. |
Problems discussed in videos |
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Optics |
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Physics: “Lenses and mirrors.
Snell’s law”. Radius of curvature. Plane
mirrors; ray tracing. Magnification. Special
cases--object distance = infinity; object distance = f; object distance = 2f;
object distance = 0. Reflection. The
speed of light and index of refraction. Refraction;
Snell’s law. |
Problems discussed in videos |
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Optics |
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Physics: “Lenses, mirrors, the eye”. Lenses and mirrors. Magnification. Ray tracing. Optics of the eye—normal vision |
Optics |
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Physics: “Lenses, mirrors, reflection, refraction”. Lenses, mirrors, ray tracing. Reflection. Refraction; Snell's Law; the index of refraction; n=c/v |
Optics |
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Problem discussed in video (1) |
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Physics: “Huygens’ principle; mirrors; the eye”. Huygens’ principle. A lens/mirror problem. An eye problem. |
Optics |
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Problems discussed in videos |
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Physics: “Light, lenses, mirrors; relativity”. Light and waves. Lenses and mirrors. A relativity problem. |
Optics |
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Problems discussed in videos |
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Physics: “Interference and diffraction”. "In phase" vs. "out of phase". Constructive vs. destructive interference. Double-slit interference. Multiple slit interference / diffraction gratings. Single-slit diffraction; Huygens' principle. Thin films |
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Physics: “Thin films”. Thin films. Double-slit interference |
Problems discussed in this video series |
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Physics: “Thin films; the eye; lenses and mirrors”. A relativity problem. A problem involving the Doppler effect and diffraction gratings. Thin films. Optics of the eye and of corrective lenses. Lenses and mirrors |
Problems discussed in this video series |
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Optics |
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Physics: “Intensity of EM waves. Multiple lenses”. Power, intensity, and radiation pressure from electromagnetic waves; the Poynting vector. A multiple lens problem. An eye problem. A contact lens problem |
Problems discussed in this video series |
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Optics |
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Physics: “Polarization.
Total internal reflection”. Polarization of light;
the law of Malus. CDs, DVDs, and the
diffraction limit. A glasses problem. Refraction, Snell's law, total internal reflection. The Brewster (polarizing) angle. |
Problems discussed in this video series |
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Physics: “Intensity. Multiple
lenses. Polarization”. Electromagnetic
waves—intensity, power, peak electric and magnetic
fields. Ray tracing for multiple lenses. Polarization. The Brewster (polarizing)
angle. A camera problem. |
Problems discussed in this video series |
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Optics |
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Physics: “De Broglie wavelength. Bohr atom”. Quantum mechanics--wave/particle duality and quantization. Photons: wavelength, energy, frequency (E=hf). Electrons and other particles with mass: de Broglie wavelength, momentum, energy. The Bohr model of the atom |
Problems discussed in this video series |
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Physics: “De Broglie wavelength. Photon energy”. Power and intensity of electromagnetic wavefronts. Blackbody radiation. Photons (E=hf). The de Broglie wavelength. The Bohr atom |
Problems discussed in this video series |
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Physics: “Photoelectric effect”. Quantum mechanics. Photoelectric effect. De Broglie wavelength. Heisenberg’s uncertainty principle. |
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Physics: “Quantum numbers. Intensity, photons”. Quantum mechanics. Quantum numbers and the periodic table; allowed quantum numbers. Problems about intensity, photon energy (E=hf), de Broglie wavelength, and the Bohr model of the atom. |
Problems discussed in this video series |
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Physics: “Particle in a box. Quantum numbers”. Quantum mechanics. Infinite square well (“particle in a box”)—how to calculate probabilities using the wave function; electron energy-level transitions via photon absorption. Quantum numbers and the periodic table; allowed quantum numbers |
Problems discussed in this video series |
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Physics: “Some quantum number problems”. Some quantum number problems, involving possible quantum numbers and ground-state electron configurations |
Problems discussed in this video series |
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Physics: “Nuclear physics”. Nuclear physics. Protons, neutrons, and electrons. Mass number (A) and atomic number (“charge number”, Z); conventional symbolism for nuclei. Alpha, beta, and gamma particles; alpha, beta, and gamma decay. Mathematics of radioactive decay; decay constant; half-life. Radioactive dating (carbon-14) |
Problems discussed in this video series |
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Physics: “More nuclear physics”. Nuclear physics. Protons, neutrons, and electrons. Mass number (A) and atomic number (“charge number”, Z); conventional symbolism for nuclei. Alpha, beta, and gamma particles; how decay particles behave in magnetic fields. Mathematics of radioactive decay; decay constant; half-life. Biological effects of radiation; rads, RBE (relative biological effect), rems. |
Problems discussed in this video series |
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Physics: “Mass defect and binding energy”. Nuclear physics—mass defect and binding energy. |
Table and problem discussed in this video series |
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Chemistry: “Chemical bonding: energy vs. distance graph”. Graph of energy vs. internuclear distance; chemical bonding, bond length, and bond energy |
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Chemistry: “Buffer solutions. Logarithms”. Qualitative introduction to buffer solutions (acid/base chemistry). How to approximate logarithms and pHs without a calculator. |
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Chemistry: “Buffers. The Henderson-Hasselbach equation”. How to solve quantitative problems about buffer solutions using the Henderson-Hasselbach equation (acid/base chemistry) |
Problem discussed in the videos |
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Chemistry: “Determining pH for acid-base titrations”. Finding pH at various points on a titration curve. Titration of a strong acid with a strong base--vertical intercept; left of equivalence point; equivalence point; right of equivalence point. Titration of a weak acid with a strong base—vertical intercept; half-equivalence point; equivalence point; right of equivalence point. How to do titration calculations without a calculator |
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Chemistry: “Kinetics--rate laws from experimental data”. Kinetics--determining the rate law from experimental data through the method of initial rates. Exponents, rate constant, units for the rate constant. Order of the reaction |
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Chemistry: “Electrochemistry and electrochemical cells”. Electrochemistry and electrochemical cells. Anode vs. cathode; oxidation vs. reduction; reduction potentials, oxidation potentials, and cell potentials; electron flow; positive and negative electrodes for galvanic vs. electrolytic cells |
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Organic chemistry: how to draw resonance structures |
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Organic chemistry: “Orbital hybridization. Sigma and pi bonds”. Hybridization
of atomic orbitals: sp3, sp2,
and sp hybridizations. Sigma vs. pi bonds. |
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Organic chemistry: “IUPAC nomenclature for branched substituents” |
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Organic chemistry: “R and S naming” |
Stereochemistry |
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Organic chemistry: “R and S naming problems”. |
Stereochemistry |
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Organic chemistry: “Stereochemistry”. Stereochemistry. Chiral carbons ("stereocenters") vs. chiral molecules. Meso molecules. Enantiomers and diastereomers. R and S naming |
Stereochemistry |
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Organic chemistry: “Stereochemistry and meso molecules” |
Stereochemistry |
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Organic chemistry: “Electron-pushing arrows”. How to use electron-pushing arrows, also known as “curved arrows,” to draw intermediates and products in reaction mechanisms. |
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Organic chemistry: more on electron-pushing arrows |
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Organic chemistry: “SN2—‘ionically bonded’ nucleophiles”. How to use electron-pushing arrows and numbering to draw the product of an SN2 reaction. How to recognize “ionically bonded” nucleophiles. |
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Organic chemistry: Three types of SN2 reaction |
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Organic chemistry: “SN2, SN1, E2, and E1 reactions” |
Reactivity and arrow-pushing |
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SN2, SN1, E2, E1 |
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Organic chemistry: “E2 reactions”. Introduction to the E2 mechanism. E2 stereochemistry--cis vs. trans, determined by anti-periplanar transition state. Protic vs. aprotic solvents. SN2 stereochemistry |
SN2, SN1, E2, E1 (this revised handout differs somewhat from the older version discussed in the video) |
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Organic chemistry: “SN2 and E2 topics”. How to determine whether a reaction will be SN2, SN1, E2, or E1. Sulfonates; the “tosyl” (Ts, toluenesulfonyl) group; “tosylate” (TsOR, toluenesulfonate). How to rank compounds in order of nucleophilicity. |
SN2, SN1, E2, E1 |
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Organic chemistry: “More on SN2, SN1, E2, and E1 reactions” |
Stereochemistry |
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SN2, SN1, E2, E1 (this revised handout differs somewhat from the older version discussed in the video) |
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Organic chemistry: “Some SN2, SN1, E2, and E1 topics”. Polar protic vs. aprotic solvents. Carbocation rearrangements. E2 and E1 regiochemistry (Zaitsev vs. Hofmann). Antiperiplanar transition state for E2; E2 and cyclohexane |
SN2, SN1, E2, E1 |
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Organic chemistry: “Introduction to Grignard reagents”. Reaction of Grignard reagents as bases with protic solvents. Reaction of Grignards as nucleophiles with aldehydes and ketones. Introduction to synthesis with Grignards. |
SN2, SN1, E2, E1 |
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Organic chemistry: “Alcohol nomenclature” |
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Organic chemistry: “Alcohols, oxidation, and reduction”. Oxidation of alcohols (PCC). Reduction of aldehydes and ketones with Grignards to form alcohols. Synthesis with Grignards. Reduction of aldehydes with NaBH4 or LiAlH4 to form alcohols. |
Reduction and oxidation with alcohols |
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Organic chemistry: “Alcohols”. Reaction of alcohols with acids and bases. Oxidation and reduction involving alcohols—PCC, Grignard reagents. |
SN2, SN1, E2, E1 |
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Reduction and oxidation with alcohols |
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Organic chemistry: “Grignards”. How to make Grignards and alkyl lithiums (organometallics). Reactions of Grignards and alkyl lithiums (with protic solvents, aldehydes and ketones, and epoxides/oxacyclopropanes). Synthesis problems—using radical halogenation, E2, SN2, oxidation (PCC), and Grignards for synthesis. The “retrosynthesis” technique for solving synthesis problems. |
Radical halogenation of alkanes |
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SN2, SN1, E2, E1 |
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Reduction and oxidation with alcohols |
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Organic chemistry: “Organometallics”. Halogenation of alcohols (PBr3,
SOCl2). Organometallics (Grignards,
alkyl lithiums, organocuprates).
Using the retrosynthesis
technique to solve synthesis problems involving organocuprates
(Gilman reagents). |
SN2, SN1, E2, E1 |
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R- and H- |
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Reduction and oxidation with alcohols |
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Organic chemistry: “Ethers”. Ethers. Williamson ether synthesis (preparation of ethers via SN2); retrosynthesis. Digression on how to remember the Brønsted-Lowry and Lewis definitions of acids and bases. Cleavage of ethers with haloacid (HX). Effect of positive formal charges on reactivity. Effect of acid or base on reactivity. |
SN2, SN1, E2, E1 |
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Reactivity and arrow-pushing |
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Organic chemistry: “Oxacyclopropanes, also known as epoxides”. Oxacyclopropanes, also known as epoxides, oxiranes, or ethylene oxides. Ring strain. Synthesis of oxacyclopropanes with peroxycarboxylic acids (“peracids”) such as peracetic acid or MCPBA. Acid-catalyzed ring opening; ring opening with anionic nucleophiles; ring opening with lithium aluminum hydride (LiAlH4). Diol (“glycol”) synthesis--anti dihydroxylation of an alkene via hydrolysis of oxacyclopropane intermediate; syn dihydroxylation of an alkene with osmium tetroxide (OsO4). Effect of a negative formal charge on reactivity. Regiochemistry of oxacyclopropane ring opening—when does the nucleophile attack the more substituted carbon and when does it attack the less substituted carbon? |
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Organic chemistry: “Introduction to proton NMR spectroscopy”. Introduction to proton NMR (nuclear magnetic resonance) spectroscopy. Equivalent vs. nonequivalent hydrogens; chemical shift; integration; spin-spin splitting. |
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Organic chemistry: “Another introduction to proton NMR”. Introduction to proton NMR (nuclear magnetic resonance) spectroscopy. Equivalent vs. nonequivalent hydrogens; chemical shift; integration; spin-spin splitting. Degrees of unsaturation |
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Organic chemistry: “Proton NMR problems”. Proton NMR (nuclear magnetic resonance) problems |
NMR table and problems |
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Organic chemistry: “Infrared spectroscopy problems” |
Problems discussed in the videos |
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Organic chemistry: “Introduction to mass spectrometry”. Mass spectrometry. Molecular/parent ion; base peak. Carbon-13; bromine and chlorine isotopes. Fragmentation and substitution |
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Organic chemistry: “Addition to alkenes: H2, HX, H2O”. Alkene addition reactions. Addition of H2 (hydrogenation). Electrophilic additions: addition of HX (hydrohalogenation); addition of H2SO4, H2O (hydration); addition of H2SO4, ROH. Addition of HX in presence of ROOR (radical addition using peroxide initiator). Regiochemistry: Markovnikov vs. anti-Markovnikov |
Alkenes |
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SN2, SN1, E2, E1 |
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Reactivity and arrow-pushing |
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Organic chemistry: “Alkenes: hydrogenation; addition of HX”. Addition reactions with alkenes: addition of H2 (hydrogenation); electrophilic addition of HX (hydrohalogenation). Markovnikov vs. anti-Markovnikov. |
Alkenes |
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Organic chemistry: “Addition of halogens (HX or X2) to alkenes”. Addition to alkenes. Electrophilic addition of HX (halohydrogenation). Addition of H2 (hydrogenation). Addition of HBr with ROOR (radical addition). Addition of Br2 or Cl2 (halogenation). |
Reactivity and arrow-pushing |
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Alkenes |
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Organic chemistry: “Alkenes: addition of HBr, BH3, X2”. Alkene addition reactions. Addition of H2 (hydrogenation). Addition of HBr, with or without peroxides. Addition of BH3 to get alcohols (hydroboration-oxidation). Addition of X2. |
Alkenes |
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Reactivity and arrow-pushing |
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Organic chemistry: “Hydrogenation and halogenation”. Alkene addition reactions. Problems involving degrees of unsaturation and hydrogenation (addition of H2). E/Z naming of alkenes. Problems involving addition of X2 (halogenation). Forming alkenes from alcohols via E1 (dehydration with H2SO4) or E2. |
Problems discussed in this video series |
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SN2, SN1, E2, E1 |
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Organic chemistry: “Synthesis of alcohols from alkenes”. Alkene addition reactions. Addition of HX, with or without peroxides. Addition of sulfuric acid and water (hydration). Addition of BH3 (hydroboration-oxidation). Oxymercuration-demercuration. Addition of X2 in alcohol. Creation of expoxides (oxacyclopropanes): from alkenes using MCPBA; from vicinal haloalcohols with base. Ozonolysis. |
Alkenes |
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Reduction and oxidation with alcohols |
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Organic chemistry: “Dihydroxylation of alkenes”. Alkene addition reactions. Addition of OsO4 (osmium tetroxide) to achieve syn dihydroxylation. Using epoxides to achieve anti dihydroxylation. A synthesis problem. The synthetic toolbox. When does steric hindrance block one face of a trigonal planar intermediate? |
Synthetic toolbox |
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Organic chemistry: “Synthesis using addition to alkenes”. Some synthesis problems involving alkenes and electrophilic addition. |
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Organic chemistry: “Alkyne synthesis and reactions”. Electronegativity of alkyne carbons; acidity of alkynes; use of alkynyl anions as nucleophiles for SN2 reactions and for attack on oxacyclopropanes (epoxides). Alkyne synthesis from dihaloalkanes by double elimination; alkyne synthesis from alkenes by halogenation-double dehydrohalogenation. Alkyne reactions. Hydrogenation of alkynes; hydrogenation of alkynes with Lindlar catalyst to form cis alkenes; sequential one-electron reduction of alkynes with sodium metal to form trans alkenes. Electrophilic addition of HX to alkynes; electrophilic addition of X2 to alkynes (halogenation). Enols; tautomerization; mercuric ion-catalyzed hydration of alkynes to form ketones |
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Organic chemistry: “Radical halogenation reactions”. Radical halogenation via radical chain
mechanisms. Radical halogenation of alkanes (a
radical substitution reaction). Radical allylic halogenation using NBS
(radical substitution). Radical addition of hydrogen bromide to
alkenes in the presence of peroxides (an anti-Markovnikov
addition). |
Radical halogenation of alkanes |
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Alkenes |
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Organic chemistry: “Synthesis problems”. Single- and multi-step synthesis problems. (First-semester final exam review session.) |
Problems discussed in the videos |
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SN2, SN1, E2, E1 |
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Synthetic toolbox |
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Organic chemistry: “Organic chemistry tips” |
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Organic chemistry: “Electrophilic attack on conjugated dienes”. Conjugation. UV-vis (ultraviolet-visible) spectroscopy. Electrophilic attack on conjugated dienes (1,2- and 1,4-addition). |
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Organic chemistry: “Radical allylic halogenation”. Radical allylic halogenation
using NBS (N-bromosuccinimide). |
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Organic chemistry: “Conjugated pi molecular orbitals”. Pi molecular orbital diagrams for conjugated systems. HOMO and LUMO |
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Organic chemistry: “Diels-Alder reaction”. Diels-Alder reaction. Dienes, dienophiles; s-cis, s-trans; electron-donating and electron-withdrawing substituents; “outside” vs. “inside” positions; “endo” vs. “exo” approaches. Molecular orbital diagram for Diels-Alder transition state (Frontier Molecular Orbital Theory); molecular orbital diagrams for endo vs. exo transition states. |
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Organic chemistry: “Retro
Diels-Alder reaction”.
The Diels-Alder and retro
Diels-Alder reactions. A
synthesis problem. |
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Organic chemistry: “Electrocyclic reactions”. Electrocyclic reactions (a type of “pericyclic”
reaction”). Woodward-Hoffmann
selection rules; conrotatory vs
disrotatory. Molecular orbital explanation
for the selection rules, using Frontier Molecular Orbital Theory |
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Organic chemistry: “Huckel’s rule: aromatic vs. antiaromatic”. Using Huckel’s rule to determine whether a molecule is aromatic, antiaromatic, or nonaromatic |
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Organic chemistry: “Benzenes and phenols”. Benzene nomenclature; “phenyl” vs. “benzyl”; ortho, meta, and para. Phenol nomenclature. Acidity of phenols. Deprotonated phenols as nucleophiles; preparation of alkyl aryl ethers using Williamson ether synthesis. Kolbe carboxylation. Hydrogenolysis of benzylic ethers |
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Organic chemistry: “Electrophilic aromatic substitution”. Electrophilic aromatic substitution (EAS) of benzene—halogenation, nitration, sulfonation, Friedel-Crafts alkylation and alkanoylation. Electron-withdrawing and electron-donating groups—activators vs deactivators, ortho/para-directors vs. meta-directors. |
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Organic chemistry: “Electrophilic aromatic substitution problems” |
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Organic chemistry: “Synthetic
strategies for substituted benzenes”. Strategies for synthesizing substituted
benzenes using electrophilic aromatic
substitutions--interconversion of nitro and amino substituents; interconversion
of alkanoyl and alkyl substituents,
Clemmensen reduction, disadvantages of Friedel-Crafts alkylation (rearrangements and overalkylation); reversible sulfonation
as a blocking procedure; moderating the activating power of amino and hydroxy substituents. Arenediazonium
salts; Sandmeyer reactions; synthesis of phenol
from an arenediazonium salt. “Phenyl”
vs. “benzyl”; oxidation of benzylic
carbons to carboxylic acids with hot potassium permanganate (KMnO4) |
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Organic chemistry: “Nucleophilic aromatic substitution”. Nucleophilic aromatic substitution of benzene. Substitution through benzyne intermediates. Summary of methods for synthesis of phenols. Benzylic oxidation to carboxylic acids; synthesis problems involving benzylic oxidation. Radical benzylic halogenation |
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Organic chemistry: “Aldehydes and ketones. Acetals and ketals”. Nucleophilic attack
on aldehydes and ketones;
the three main categories of nucleophilic attack.
A category 1 reaction: attack by a Grignard to
form an alcohol. A category
2 reaction: attack by alcohol in acidic conditions to form an acetal or ketal. A category 2 “reverse” reaction: reaction of
an acetal or ketal with
aqueous acid to form an aldehyde or ketone. How treatment of reagents with acid or base
affects reactivity |
Nucleophilic attack on aldehydes and ketones |
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Organic chemistry: “More on aldehydes and ketones”. Nucleophilic attack on aldehydes and ketones; the three main categories of nucleophilic attack. Two category 1 reactions: attack by a Grignard to form an alcohol; attack by LAH to form an alcohol. A category 2 reaction: attack by alcohol in acidic conditions to form an acetal or ketal. A category 2 “reverse” reaction: reaction of an acetal or ketal with aqueous acid to form an aldehyde or ketone |
Nucleophilic attack on aldehydes and ketones |
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Organic chemistry: “Aldehyde and ketone
problems”. Aldehyde/ketone nomenclature problems. Spectroscopy problems. Hydration
(nucleophilic addition of water to aldehydes and ketones to form geminal diols. Reactivity of aldehydes and ketones. Effects of acid or base
on reactivity. Mass spectrometry of aldehydes and ketones; McLafferty rearrangement. Nucleophilic addition of thiols to aldehydes and ketones to form thioacetals;
desulfurization of thioacetals with Raney nickel.
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Nucleophilic attack on aldehydes and ketones |
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Organic chemistry: “Attack of amines on aldehydes and ketones”. Nucleophilic attack by amines on aldehydes and ketones to form imines (category 3) and enamines (category 4). Wolff-Kishner reduction. Nucleophilic addition by hydrogen cyanide on aldehydes and ketones (category 1). The Wittig reaction (category 3); how to make phosphorus ylides |
Nucleophilic attack on aldehydes and ketones |
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Organic chemistry: “Baeyer-Villiger oxidation”. Baeyer-Villiger oxidation of aldehydes and ketones to form esters. Oxidation of aldehydes to form carboxylic acids |
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Organic chemistry: “Enols and tautomerism”. Enols and enolates; tautomerism. Racemization at an α-carbon; deuterium exchange at an α-carbon. Enols as nucleophiles; acid-catalyzed α-halogenation. Boiling point of aldehydes and ketones |
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Organic chemistry: “Aldehydes, ketones, enolates”. Nucleophilic attack on aldehydes and ketones; acetals and ketals. Enolates. Ylides; Wittig reaction. Mechanism problems. |
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Organic chemistry: “Aldol condensation”. Enolates. Tautomerism between aldehydes or ketones and enols. Aldol condensation |
Nucleophilic attack on aldehydes and ketones |
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Organic chemistry: “1,2- and 1,4-addition”. 1,2-addition and 1,4-addition (“conjugate addition”) to α,β-unsaturated aldehydes and ketones. (This video does not cover 1,2- or 1,4-addition to dienes; that material is covered in the video “Electrophilic attack on conjugated dienes”.) |
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Organic chemistry: “Michael addition. Robinson annulation”. Michael addition (conjugate addition of enolate ions). Robinson annulation (Michael addition followed by aldol condensation). |
Nucleophilic attack on aldehydes and ketones |
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Organic chemistry: “Naming aldehydes, ketones, carboxylic acids”. Nomenclature for aldehydes, ketones, carboxylic acids, and ethers. General names for the types of carboxylic acid derivatives |
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Organic chemistry: “Carboxylic acids and acid derivatives”. Acidity of carboxylic acids; ranking compounds in order of acidity. How to synthesize carboxylic acids: oxidation; carbonation; nitrile hydrolysis. The types of carboxylic acid derivative. The general pattern for nucleophilic attack on carboxylic acids and acid derivatives (addition-elimination). Esterification. Ranking carboxylic acids derivatives in order of reactivity |
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Organic chemistry: “Carboxylic acids”. Acidity of carboxylic acids; ranking compounds in order of acidity; acid/base reactions with carboxylic acids; extraction (laboratory separation technique). Carbonation (reaction of Grignard reagent with carbon dioxide to form carboxylic acid). Reduction of carboxylic acids with lithium aluminum hydride (LiAlH4, or LAH) to form alcohols. Reaction of carboxylic acids with SOCl2 (thionyl chloride) to form acyl chlorides. Decarboxylation |
Reactivity and arrow-pushing |
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Organic chemistry: “Nomenclature for carboxylic acid derivatives”. Nomenclature for acyl halides, anhydrides, esters, amides, nitriles. |
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Organic chemistry: “Carboxylic acid derivatives”. Nucleophilic attack on carboxylic acid derivatives, including hydrolysis, saponification, transesterification. |
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Organic chemistry: “More on carboxylic acid derivatives”. Nucleophilic attack on carboxylic acid derivatives, including transesterification, ester hydrolysis, attack by Grignards on esters, amide hydrolysis |
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Organic chemistry: “Hydrolysis of carboxylic acid derivatives”. Hydrolysis of carboxylic acid derivatives (acyl halides, anhydrides, esters, amides, and nitriles) to form carboxylic acids. Nucleophilic attack of alcohols and amines on carboxylic acids and acid derivatives to form esters and amides. Lithium aluminum hydride reduction of aldehydes and ketones, carboxylic acids, and esters to form alcohols |
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Organic chemistry: “Claisen condensation. 1,3-dicarbonyls”.
Overview of nucleophilic
attacks on carboxylic acids and acid derivatives through the
addition-elimination mechanism. How to make 1,3-dicarbonyls through the Claisen
condensation; the Dieckmann condensation (intramolecular Claisen
condensation). Reactions of 1,3-dicarbonyls—acetoacetic
ester synthesis; malonic ester synthesis |
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Organic chemistry: “Reactions of enamines and enolates”. Enamine formation through attack of secondary amines on aldehydes and ketones; enamines as nucleophiles; alkylation of enamines; synthesis problems involving enamines. Aldol condensation; crossed aldol condensation; intramolecular aldol condensation. Claisen condensation; intramolecular Claisen condensation; crossed Claisen condensation; Claisen condensation as a route to ketones. Acetoacetic ester synthesis; malonic ester synthesis. Michael addition; Michael acceptors; Michael donors |
Nucleophilic attack on aldehydes and ketones |
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Organic chemistry: “Introduction to amines”. Amine nomenclature. Nucleophilicity and basicity of amines. Synthesis of amines—through SN2, through lithium aluminum hydride (LAH) reduction of amides or nitriles, through the Gabriel synthesis, or through reductive amination. Overview of LAH reductions—of aldehydes and ketones, of carboxylic acids, of esters, of amides, and of nitriles. |
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Organic chemistry: “Basicity of aliphatic and aromatic amines” |
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Organic chemistry:
“Carbohydrates”.
Carbohydrates (sugars). D
vs. L sugars; epimers. Ring formation; |
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Organic chemistry: “Introduction to amino acids and peptides”. Biochemistry. How to draw amino acids. Acid/base properties of amino acids. Finding net charge of amino acids and peptides (proteins) at a specified pH. pI of amino acids and peptides. Peptide (amide) bonds. Amino acid sequencing with partial digestion by proteolytic enzymes such as trypsin. Total acid hydrolysis (TAH) |
Amino acid table |
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Problem discussed in videos |
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Organic chemistry: “Amino acids and peptides”. Biochemistry--amino acids, peptides, and polypeptide sequencing. Acid/base properties of amino acids. How to draw amino acids at various pH’s. How to determine pI of a peptide; zwitterion. Acylation of the N-terminus; conversion of the C-terminus into an amide. Total acid hydrolysis (TAH). Sanger’s reagent and Dansyl chloride. Hydrazine (NH2NH2). Proteolytic enzymes--chymotrypsin, trypsin, thermolysin. A polypeptide sequencing problem |
Amino acid table |
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Problems discussed in videos |
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Organic chemistry: “Amino acid and polypeptide synthesis”. Amino acid synthesis--Gabriel synthesis; Strecker synthesis. Edman degradation. Polypeptide synthesis--Cbz (carbobenzoxy) and Boc (tert-butoxycarbonyl) amino-protecting groups; protection of the carboxy terminus via ester formation; DCC (dicyclohexylcarbodiimide) carboxy-activating reagent. An example of calculating pI and charge at a specific pH for a long polypeptide |
Amino acid table |
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Biology: “Mendelian
genetics”. Mendelian genetics. A Mendelian genetics
problem, using a Punnett square. Law of segregation. Law of independent
assortment. Exception to the law of independent
assortment: linked genes. Crossing over. Wild
type vs. mutant phenotype (Morgan notation); true-breeding plants |
Problems discussed in the videos |
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