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Video descriptions |
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Document descriptions |
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Physics: ratio units |
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Physics: “One-dimensional
kinematics”. 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: “Multi-part one-dimensional motion
problems”.
Multi-part one-dimensional kinematics problems.
A multiple-object kinematics problem |
Problems discussed in the videos |
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Kinematics equations and method |
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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. Gravitational
potential energy. Total mechanical energy. Conservation of mechanical energy. Spring
potential energy. Conservation of energy problems |
Work and energy |
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Physics: “More on work and 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 |
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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 |
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 |
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: “Application of Gauss's law to line
symmetry”.
Using Gauss's law to determine the electric field
from a charge distribution with line symmetry. Determining
the electric potential difference from a nonuniform
electric field. |
Problem discussed in the videos |
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Electric field and force; electric potential and potential
energy |
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Physics: “Electric circuits. Resistors”. 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: “Electromagnetic induction. Faraday's law”. Magnetic flux. Electromagnetic
induction; induced emf; induced current. Faraday's law
of induction; Lenz's law.
Two problems with changing magnetic field; a problem with changing area |
Electric field and force; electric potential and potential
energy |
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Magnetic field and force |
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Electromagnetic induction |
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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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GENERAL CHEMISTRY |
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Video descriptions |
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Document descriptions |
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Chemistry: ratio units |
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Chemistry: “Stoichiometry.
Atoms, molecules, moles”. Stoichiometry. Atoms and molecules.
Unit conversion, metric prefixes, equivalence statements. Atomic
mass unit (amu), mole, Avogadro's number, molar
mass. Converting between grams and moles; converting between grams and
atoms or molecules |
Problem discussed in the videos |
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Conversion factors discussed in the videos |
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Sources of equivalence statements |
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Chemistry: “Stoichiometry. ICE tables. Limiting
reagent”. Stoichiometry. Balancing chemical equations. Initial-change-end (ICE) tables. Using stoichiometric calculations to determine the amounts of reactants
and products. Limiting reagent |
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Chemistry: “Stoichiometry
problems”. Stoichiometry problems. Atomic mass of
naturally occurring isotopes. “Mixture problems” |
Problems discussed in the videos |
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Chemistry: “Mass spectrometry
problems”. Stoichiometry problems involving mass spectrometry |
Problems discussed in the videos |
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Chemistry: “Equilibrium. Le Châtelier’s
Principle”. Chemical equilibrium. Reaction quotient (Q). Equilibrium
constant (K). Le Châtelier’s
principle |
Equilibrium and completion reactions |
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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: “Acids and bases. Calculating pH.
Titrations”. Acids and bases. Calculating pH and pOH. Water autoionization; water ion-product constant (Kw). Acid dissociation
constant (Ka). Buffer solutions;
Henderson-Hasselbach equation. Titrations;
equivalence point; half-equivalence point |
Types of acid/base problems |
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Problems discussed in the videos |
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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: “Calculating pH for
acid-base titrations”. Calculating 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 |
Types of acid/base problems |
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Chemistry: “Solubility product (Ksp)
and molar solubility”. Dissolution and precipitation reactions. Solubility product (Ksp) and
ion product (Q). Application of ICE tables to dissolution reactions. Molar solubility. How to find the
solubility from the Ksp; how to find the
Ksp from the solubility. Common
ion effect |
Solubility |
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Chemistry: “Photoelectric
effect”. Energy, frequency, and wavelength of photons. Photoelectric effect |
Problems discussed in the videos |
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Chemistry: “Bohr model
problems”. Problems involving the Bohr model of electronic
transitions for the hydrogen atom and other one-electron species |
Problems discussed in the videos |
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Chemistry: “Quantum numbers” |
Problems discussed in the videos |
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Chemistry: “Kinetics--rate laws
from experimental data”. Chemical
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: “Differential and integrated rate laws”. Chemical
kinetics. Differential rate laws. Method of initial rates. Rate constant;
order of the reaction. Zero-order, first-order, and
second-order integrated rate laws. |
Problems discussed in the videos |
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Table discussed in the videos |
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Chemistry: “Chemical kinetics.
Reaction mechanisms”. Chemical kinetics. Reaction mechanisms. Elementary steps; molecularity (unimolecular, bimolecular, termolecular).
Rate laws for the overall reaction and for elementary steps. Rate-determining step. Mechanisms with slow
first steps. Mechanisms with fast forward and reverse first steps |
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Chemistry: “Arrhenius equation.
Activation energy”. Chemical kinetics. Arrhenius equation. Logarithms. Activation energy. Reaction energy diagram. Transition
state. Catalysis |
Logarithm properties |
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Chemistry: “Balancing redox
reactions”.
Electrochemistry. Oxidation and
reduction. Oxidizing agent and reducing agent.
Oxidation number, also known as oxidation state.
Balancing oxidation-reduction reactions, also known as redox
reactions, using the half-reaction method in acidic and basic solutions |
Redox reactions |
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Chemistry: “Electrochemistry and
electrochemical cells”. Electrochemistry
and electrochemical cells. Oxidation and reduction; oxidizing agents
vs. reducing agents. Galvanic/voltaic cells. Cathode, anode. Free energy and cell
potential. Half-reactions; reduction potentials,
oxidation potentials. Salt bridge. Calculating cell potential. Faraday's constant. Work. Equilibrium constant. Nernst equation. Electrolytic cells |
Problem discussed in the videos |
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Table discussed in the videos |
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Chemistry: “More on
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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Chemistry: “Molecular orbital model”. Molecular
orbital model of covalent bonding. Molecular orbital (MO) energy-level diagrams. Sigma and pi
molecular orbitals; bonding and antibonding
molecular orbitals; bond order; paramagnetism
and diamagnetism. Bonding in homonuclear and
heteronuclear diatomic molecules |
Figure discussed in the videos |
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Chemistry: “Transition metals and isomerism”. Transition
metals and isomerism. Transition metal electron
configurations for neutral atoms and cations.
Coordination compounds; oxidation number and coordination
number. Coordination isomers; linkage isomers.
Structural isomers vs. stereoisomers. Geometric isomers. Optical isomers |
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Chemistry: “More on transition metals and isomerism”. Transition metals and
coordination compounds. Electron configurations for
neutral and cation transition metals. Coordination number; oxidation number. Bidentate ligands;
ethylenediamine (“en”). Complex ion geometries (octahedral, square planar, tetrahedral,
linear). Isomerism. Geometric
isomers; cis and trans. Optical isomers;
enantiomers. |
Tables discussed in the videos |
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Chemistry: “Nomenclature for coordination compounds”. Nomenclature for transition metal
coordination compounds |
Tables discussed in the videos |
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Chemistry: “Transition metals and the crystal field model”. Transition
metals and the crystal field model. Strong-field case and
weak-field case; low-spin case and high-spin case; paramagnetism
and diamagnetism; spectrochemical series; colors of
complex ions. The localized electron model of bonding in complex ions,
also known as the valence bond model |
Figures discussed in the videos |
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Chemistry: “Kinetics of
radioactive decay. Half-life”. Nuclear chemistry. Kinetics of radioactive
decay. Decay constant; rate of decay (“activity”). Half-life. Integrated rate law for radioactive decay and
other key equations |
Problems discussed in the videos |
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Nuclear chemistry |
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Logarithm properties |
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Chemistry: “Nuclear chemistry. Binding energy”. Nuclear chemistry. Atomic number, mass
number. Mass defect and binding energy |
Nuclear chemistry |
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Chemistry: “IUPAC alkane nomenclature”. Introductory
organic chemistry topics from the perspective of a general chemistry course.
IUPAC alkane
nomenclature. Bond-line notation. How to draw all the
structural isomers of a compound. Common names for
branched substituents: isopropyl, isobutyl,
sec-butyl, tert-butyl. Naming cyclic alkanes |
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ORGANIC CHEMISTRY |
I receive a referral fee for any items purchased via this link. |
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Video descriptions |
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Document descriptions |
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Organic chemistry: “Introduction to drawing resonance
structures”. How to
draw resonance structures. |
Resonance structures |
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Organic chemistry: “How to draw
resonance structures”. The meaning of
resonance. The purpose of resonance is to determine the locations of
the charges. How to interpret electron-pushing arrows.
Rules for drawing legal and significant resonance
structures. |
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 alkane nomenclature”. IUPAC
alkane nomenclature. Bond-line notation.
How to draw all the structural isomers of a compound.
Common names for branched substituents
(isopropyl, isobutyl, sec-butyl, tert-butyl).
Naming cyclic alkanes |
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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. |
Proton NMR spectroscopy |
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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 |
Proton NMR spectroscopy |
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Organic chemistry: “Proton NMR
problems”. Proton NMR (nuclear magnetic resonance) problems |
NMR table and problems |
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Proton NMR spectroscopy |
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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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I recommend this
book:
I receive a referral fee for any items purchased via this link. |
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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: “A radical allylic halogenation problem”. A synthesis problem involving
radical allylic halogenation |
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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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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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Video descriptions |
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Document descriptions |
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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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