Preparation for Organic Chemistry - ALEKS

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Preparation for Organic Chemistry
This course covers the topics shown below.
Students navigate learning paths based on their level of readiness.
Institutional users may customize the scope and sequence to meet curricular needs.
Curriculum (184 topics + 438 additional topics)
   General Chemistry Review (122 topics)

      Electrostatics (5 topics)
           Understanding that opposite charges attract and like charges repel
           Understanding net electrical charge
           Understanding how electrostatic f orces cancel
           Understanding how electrostatic energy scales with charge and separation
           Sketching polarization induced by a nearby charge
      Chemical Elements (4 topics)
          Understanding periods and groups of the Periodic Table
          Understanding main-group periodic trends in ionization energy
          Understanding main-group periodic trends in atomic radius
          Ranking the oxidizing power of halogens
      Atoms (6 topics)
          Identif ying the parts of an atom
          Counting protons and electrons in atoms and atomic ions
          Predicting the ions f ormed by common main-group elements
          Counting valence electrons in a neutral atom
          Counting valence electrons in an atomic ion
          Drawing the Lewis dot diagram of a main group atom or common atomic ion
      Chemical Compounds (4 topics)
          Counting the number of atoms in a f ormula unit
          Writing a chemical f ormula given a molecular model
          Writing a chemical f ormula given a chemical structure
          Understanding the prefixes used in naming binary compounds
      Ionic Compounds (3 topics)
            Predicting the f ormula of binary ionic compounds
            Identif ying common polyatomic ions
            Naming ionic compounds with common polyatomic ions
      Chemical Reactions (7 topics)
          Writing a chemical equation f rom a molecular movie
          Writing the net equation f or a sequence of reactions
          Using a chemical equation to find moles of product f rom moles of reactant
          Identif ying the limiting reactant in a drawing of a mixture
          Understanding theoretical, actual, and percent yield
          Identif ying precipitation, combustion and acid-base reactions
          Predicting products f rom a general statement about reactivity

      Solution Chemistry (3 topics)
           Identif ying the correct sketch of a compound in aqueous solution
           Writing net ionic equations
           Applying like dissolves like
      Acids and Bases (22 topics)
           Predicting the products of a neutralization reaction
           Identif ying acids and bases by their reaction with water
           Understanding the diff erence between strong and weak acids
           Identif ying Bronsted-Lowry acids and bases
           Identif ying strong or weak acids and bases f rom a sketch
           Finding the conjugate of an acid or base
           Predicting the products of the reaction of a strong acid with water
           Predicting the reactants of a neutralization reaction
           Predicting the qualitative acid-base properties of salts
           Identif ying Lewis acids and bases in reactions
           Naming inorganic acids
           Deducing the f ormulae of inorganic acids f rom their names
           Predicting the relative acidity of binary acids
           Understanding the eff ect of induction on acidity
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Calculating the pH of a strong acid solution
              Calculating the pH of a strong base solution
              Diluting a strong acid solution to a given pH
              Preparing a strong base solution with a given pH
              Writing an acid dissociation constant expression
              Determining the strength of acids f rom a sketch
              Calculating the Ka of a weak acid f rom pH
              Interconverting Ka and pKa

     Oxidation and Reduction (3 topics)
          Assigning oxidation numbers
          Recognizing reduction and oxidation
          Identif ying oxidizing and reducing agents

     Reaction Thermodynamics (0 topics)
         Using the general properties of reaction enthalpy
         Calculating the heat of reaction f rom bond energies
         Qualitatively predicting reaction entropy
         Using the Second Law to predict spontaneous change
         Using the general properties of Gibbs f ree energy
         Calculating dG f rom dH and dS
         Using the conditions of spontaneity to deduce the signs of ΔH and ΔS
         Recognizing consistency between statements about standard Gibbs f ree energy

     Quantum Mechanics (1 topics)
         Recognizing s and p orbitals

     Electronic Structure of Atoms (12 topics)
          Deciding the relative energy of electron subshells
          Calculating the capacity of electron subshells
          Knowing the subshells of an electron shell
          Interpreting the electron configuration of a neutral atom
          Writing the electron configuration of a neutral atom with s and p electrons only
          Writing the electron configuration of an atom or atomic ion with s and p electrons only
          Writing the electron configuration of an atom using the Periodic Table
          Identif ying quantum mechanics errors in electron configurations
          Identif ying elements with a similar valence electron configuration
          Predicting the relative ionization energy of elements
          Understanding periodic trends in atomic size
          Understanding periodic trends in atomic ionizability
     Atomic Spectroscopy (5 topics)
         Understanding the organization of the electromagnetic spectrum
         Interconverting the wavelength and f requency of electromagnetic radiation
         Interconverting wavelength, f requency and photon energy
         Calculating the wavelength of a spectral line f rom an energy diagram
         Predicting the qualitative f eatures of a line spectrum
     Lewis Structures (16 topics)
          Counting bonding and nonbonding electron pairs in a Lewis structure
          Counting valence electrons in a molecule or polyatomic ion
          Deciding whether a Lewis structure satisfies the octet rule
          Writing Lewis structures f or diatomic molecules
          Calculating f ormal charge
          Writing Lewis structures f or a molecule with one central atom and no octet-rule exceptions
          Writing the Lewis structures f or a molecule with resonance
          Drawing Lewis structures f or simple organic compounds
          Predicting the relative electronegativities of atoms
          Predicting relative bond polarity
          Predicting the relative length and energy of chemical bonds
          Predicting the arrangement of electron groups around the central atom of a molecule
          Predicting bond angles in a small organic molecule
          Predicting whether molecules are polar or nonpolar
          Naming common chemical groups
          Identif ying common chemical groups in a Lewis structure

     Electronic Structure of Molecules (3 topics)
          Counting sigma and pi bonds in a small molecule
          Identif ying carbon hybridization in simple organic molecules
          Recognizing typical LCAO molecular orbitals
     Intermolecular Forces (4 topics)
          Identif ying a molecule f rom its electrostatic potential map
          Predicting the strength of intermolecular f orces f rom an electrostatic potential map

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Identif ying hydrogen-bonding interactions between molecules
              Identif ying the intermolecular f orces between atoms, ions and molecules
     Chemical Kinetics (10 topics)
         Using a rate law
         Using reactant reaction order to predict changes in initial rate
         Calculating the change in concentration af ter a whole number of half -lives of a first-order reaction
         Interpreting a reaction energy diagram
         Relating activation energy to reaction rate
         Drawing the reaction energy diagram of a catalyzed reaction
         Understanding the qualitative predictions of the Arrhenius equation
         Identif ying the molecularity of an elementary reaction
         Identif ying intermediates in a reaction mechanism
         Writing the rate law of an elementary reaction

     Chemical Equilibrium (6 topics)
         Using Le Chatelier's Principle to predict the result of changing temperature
         Writing a concentration equilibrium constant expression
         Calculating an equilibrium constant f rom an equilibrium composition
         Using an equilibrium constant to predict the direction of spontaneous reaction
         Recognizing equilibrium f rom a sketch
         Predicting equilibrium composition f rom a sketch
  Structure and Bonding (39 topics)

     Drawing Organic Molecules (10 topics)
         Identif ying carbon atoms in a skeletal structure
         Interpreting the skeletal structure of a neutral organic molecule
         Drawing a skeletal structure f rom a simple condensed structure
         Drawing a skeletal structure f rom a condensed structure
         Interpreting a skeletal structure with aromatic rings
         Recognizing diff erent skeletal structures
         Understanding H atoms in a skeletal structure
         Comparing skeletal structures related by one f ewer bond
         Using wedges and dashes in skeletal structures
         Understanding dash-wedge structures
     Formal Charge (5 topics)
         Assigning f ormal charges in simple Lewis structures
         Correcting f ormal charges in complex Lewis structures
         Placing lone pairs on simple Lewis structures
         Correcting lone pair placement in complex Lewis structures
         Evaluating octet compliance at carbon
     Interpreting Condensed Formulae (2 topics)
          Drawing a Lewis structure f rom the condensed f ormula of an unsaturated molecule
          Drawing a Lewis structure f rom a condensed f ormula with parentheses

     Principles of Organic Nomenclature (11 topics)
          Naming normal alkanes
          Identif ying organic f unctional groups
          Identif ying common chemical groups in a Lewis structure
          Using f amily suffixes to name organic compounds
          Identif ying f unctional groups in organic molecules written in skeletal f ormat
          Identif ying organic f unctional groups in simple structures
          Identif ying the main chain of branched alkanes
          Naming the parent hydrocarbon of branched alkanes
          Understanding the basic descriptive vocabulary of hydrocarbons
          Understanding the basic descriptive vocabulary of molecules with f unctional groups
          Naming and drawing small alkyl substituents
     Resonance (2 topics)
         Identif ying isomers and resonance structures
         Identif ying skeletal resonance structures

     Electron Movement (6 topics)
          Determining the product of a curved arrow drawn on a Lewis structure
          Drawing simple curved arrows on a Lewis structure to show how electrons move
          Drawing cascading curved arrows on a Lewis structure to show how electrons move
          Drawing curved arrows on a skeletal structure to show how electrons move
          Determining the product of curved arrows drawn on a skeletal structure
          Recalculating f ormal charge when electrons move

     Molecular Quantum Mechanics (3 topics)

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Understanding how to make sp hybrid orbitals
              Understanding how AOs combine to make MOs
              Using hybridization to predict relative length and strength of chemical bonds

  Organic Acids and Bases (5 topics)

     Acid-Base Reactions and Mechanisms (3 topics)
          Recognizing organic acids and bases
          Identif ying acidic and basic sites on an organic molecule
          Drawing the conjugate acid or base of an organic molecule without significant C-H acidity

     Structure-Acidity Relationships (2 topics)
          Using a pKa table to rank acids and bases
          Using pKa to evaluate acid-base equilibria

  Hydrocarbons (18 topics)

     Alkanes (6 topics)
          Classif ying hydrocarbons
          Naming and drawing normal alkanes.
          Naming and drawing simple cyclic alkanes
          Naming and drawing branched alkanes
          Naming and drawing simple substituted cycloalkanes
          Identif ying primary, secondary, tertiary, and quaternary carbons

     Constitutional Isomerism (3 topics)
         Identif ying constitutional isomers
         Drawing the condensed structure of a constitutional isomer
         Drawing the skeletal structure of a constitutional isomer

     Conf ormation (7 topics)
          Drawing Newman projections of simple organic molecules
          Describing the relative positions of substituents in a Newman projection
          Drawing the Newman projection of a molecule f rom its name
          Drawing a 6-atom ring in chair perspective
          Distinguishing axial and equatorial substituents
          Drawing axial and equatorial substituents
          Interconverting line structure and chair drawing

     Unsaturated Hydrocarbons (2 topics)
         Naming and drawing normal alkynes
         Naming and drawing alkynes

  Other Topics Available(*) (438 additional topics)

     General Chemistry Review (120 topics)
         Understanding how electrostatic f orce scales with charge and separation
         Calculating the magnitude of an electrostatic f orce using Coulomb's Law
         Understanding that electrostatic f orces add as vectors
         Calculating electrostatic energy using Coulomb's Law
         Names and symbols of important elements
         Reading a Periodic Table entry
         Recognizing element f amilies
         Predicting the type of bonding in a main-group element
         Counting the number of protons and electrons in a neutral atom
         Isotopes
         Counting the electron shells in a neutral atom
         Interpreting the symbol f or a nuclide
         Knowing the properties of the common types of nuclear radiation
         Understanding the common modes of radioactive decay
         Understanding radioactive half lif e
         Understanding the diff erence between a molecular and empirical f ormula
         Naming binary covalent compounds
         Naming binary ionic compounds
         Deducing the ions in a binary ionic compound f rom its empirical f ormula
         Deducing the empirical f ormula of a binary ionic compound f rom its name
         Predicting ionic compounds f ormed by two elements
         Predicting and naming ionic compounds f ormed by two elements
         Predicting the f ormula of ionic compounds with common polyatomic ions
         Deducing the ions in a polyatomic ionic compound f rom its empirical f ormula
         Identif ying oxoanions
         Naming ionic compounds with common oxoanions
         Finding molar mass f rom chemical f ormulae
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Interconverting number of atoms and mass of compound
              Stoichiometric coefficients
              Balancing chemical equations with noninterf ering coefficients
              Balancing chemical equations with interf ering coefficients
              Writing a chemical equation f rom a description of the reaction
              Solving f or a reactant using a chemical equation
              Limiting reactants
              Theoretical yield of chemical reactions
              Percent yield of chemical reactions
              Reaction sequence stoichiometry
              Calculating molarity using solute moles
              Using molarity to find solute moles and solution volume
              Calculating molarity using solute mass
              Using molarity to find solute mass and solution volume
              Identif ying acids and bases by their chemical f ormula
              Determining the volume of base needed to titrate a given mass of acid
              Determining the molar mass of an acid by titration
              Standardizing a base solution by titration
              Predicting acid or base strength f rom the conjugate
              Predicting the qualitative acid-base properties of metal cations
              Interconverting pH and hydronium ion concentration
              Interconverting pH and pOH at 25°C
              Interconverting hydronium and hydroxide concentration at 25°C
              Identif ying the major species in weak acid or weak base equilibria
              Calculating the pH of a buff er
              Calculating the composition of a buff er of a given pH
              Writing the dissociation reactions of a polyprotic acid
              Identif ying oxidized and reduced reactants in a metal-nonmetal reaction
              Identif ying oxidized and reduced reactants in a single-displacement reaction
              Predicting whether simple electrochemical reactions happen
              Solving a redox titration problem
              Calculating the heat of reaction f rom molar reaction enthalpy and the mass of a reactant
              Using Hess's Law to calculate net reaction enthalpy
              Writing a standard f ormation reaction
              Calculating a molar heat of reaction f rom f ormation enthalpies
              Solving combustion thermochemistry problems
              Calculating the heat of reaction f rom bond energies and Lewis structures
              Calculating entropy change f rom reversible heat flow
              Calculating absolute entropy using the Boltzmann hypothesis
              Calculating entropy change using the Boltzmann hypothesis
              Predicting qualitatively how entropy changes with temperature and volume
              Predicting qualitatively how entropy changes with mixing and separation
              Calculating reaction entropy using the standard molar entropies of reactants
              Calculating standard reaction f ree energy f rom standard f ree energies of f ormation
              Interconverting standard Gibbs f ree energy and K
              Using thermodynamic data to calculate K
              Interpreting the radial probability distribution of an orbital
              Interpreting the angular probability distribution of an orbital
              Deducing n and l f rom a subshell label
              Drawing a box diagram of the electron configuration of an atom
              Deducing the allowed quantum numbers of an atomic electron
              Interpreting the electron configuration of a neutral atom in noble-gas notation
              Writing the electron configuration of a neutral atom with a filled d subshell
              Interpreting the electron configuration of an atom or atomic ion
              Interpreting the electron configuration of an atom or atomic ion in noble-gas notation
              Identif ying the electron added or removed to f orm an ion f rom an s or p block atom
              Identif ying the electron added or removed to f orm an ion
              Identif ying s, p, d and f block elements
              Understanding the definitions of ionization energy and electron affinity
              Deducing valence electron configuration f rom trends in successive ionization energies
              Ranking the screening efficacy of atomic orbitals
              Understanding periodic trends in eff ective nuclear charge
              Deducing the block of an element f rom an electron configuration
              Calculating the wavelength of a line in the spectrum of hydrogen
              Counting electron pairs in a Lewis structure with double or triple bonds
              Predicting the single-bonded molecular compounds f ormed by two elements
              Recognizing exceptions to the octet rule
              Identif ying hybridization in a small molecule
              Drawing the MO energy diagram f or a Period 2 homodiatom
              Using the MO model to predict bond order and paramagnetism
              Identif ying the important intermolecular f orces in pure compounds
              Predicting the relative strength of the dispersion f orce between molecules
              Predicting the relative boiling points of pure substances
              Predicting how reaction rate varies with pressure, concentration and temperature

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Calculating the reaction rate of one reactant f rom that of another
              Calculating average and instantaneous reaction rate f rom a graph of concentration versus time
              Deducing a rate law f rom initial reaction rate data
              Using a zero order integrated rate law to find concentration change
              Using an integrated rate law f or a first-order reaction
              Using a second-order integrated rate law to find concentration change
              Using first- and second-order integrated rate laws
              Finding half lif e and rate constant f rom a graph of concentration versus time
              Solving applied problems with first-order kinetics
              Using the Arrhenius equation to calculate k at one temperature f rom k at another
              Using the Arrhenius equation to calculate Ea f rom k versus T data
              Writing a plausible missing step f or a simple reaction mechanism
              Deducing inf ormation about reaction mechanisms f rom a reaction energy diagram
              Predicting relative f orward and reverse rates of reaction in a dynamic equilibrium
              Using Le Chatelier's Principle to predict the result of changing concentration
              Writing the concentration equilibrium expression f or a heterogeneous equilibrium
              Calculating an equilibrium constant f rom a heterogeneous equilibrium composition
              Using the general properties of equilibrium constants
              Writing an equilibrium constant f or a reaction sequence

     Structure and Bonding (21 topics)
          Interpreting a flipped or rotated dash-wedge skeletal structure
          Understanding the 3D shape of molecules with pi bonds
          Drawing a Lewis structure f or a simple organic molecule f rom a description
          Completing the Lewis structure f or an organic molecule with non-zero f ormal charges
          Identif ying hydrogen atoms in a skeletal structure
          Expanding a chemical group and drawing in lone pairs on a skeletal structure
          Converting a skeletal structure to a Lewis structure
          Drawing a skeletal structure f rom a Lewis structure
          Interpreting condensed chemical structures
          Drawing a Lewis structure f rom a condensed f ormula with N and O
          Drawing a Lewis structure f rom a condensed f ormula with a carbonyl-containing f unctional group
          Numbering the main chain of branched alkanes
          Naming and drawing alkyl and alkoxy substituents
          Drawing resonance structures with complete octets
          Ranking resonance structures
          Drawing the second best resonance structure
          Ranking the stability of carbocation intermediates
          Predicting simple carbocation rearrangements
          Drawing the mechanism f or a carbocation rearrangement in a skeletal structure
          Determining the electron group geometry and hybridization state of atoms in a skeletal structure
          Recognizing orbital representations
     Organic Acids and Bases (22 topics)
         Understanding organic acids and bases
         Drawing the conjugate of a carbon acid or base
         Drawing organic conjugate acids and bases
         Drawing the products of an organic acid-base reaction shown in condensed Lewis f ormat
         Drawing the products of an organic acid-base reaction shown in skeletal f ormat
         Drawing the structure of a missing acid or base in an equilibrium reaction
         Identif ying an organic acid-base reaction f rom its mechanism
         Drawing the mechanism of an organic acid-base reaction
         Finding ionization f raction f rom pKa f or an organic acid or base
         Predicting an organic acid-base equilibrium using structural similarity and a pKa table
         Understanding the influence of element identity on site acidity
         Using a pKa table to estimate site acidities in complex molecules
         Understanding the solvent leveling eff ect
         Using periodic trends to identif y an organic molecule's most acidic or basic site
         Understanding the influence of resonance on site acidity
         Understanding how resonance aff ects organic acid and base strength
         Understanding the influence of induction on site acidity
         Understanding how induction aff ects organic acid and base strength
         Understanding the influence of hybridization on site acidity
         Understanding how hybridization aff ects organic acid and base strength
         Identif ying the stronger base f rom its structure
         Identif ying Lewis acids and bases f rom their structures
     Hydrocarbons (16 topics)
         Using multiplying affixes in the names of branched alkanes
         Identif ying degree of carbon substitution
         Understanding partial charge notation and comparing relative bond polarities
         Identif ying isomers
         Drawing constitutional isomers
         Matching Lewis structures to a 3D model

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Identif ying bond rotations in dash-wedge skeletal structures
              Understanding how strain aff ects the energy of a conf ormation
              Understanding the relative energy of rotational conf ormations
              Drawing a molecule in chair perspective af ter a chair flip
              Identif ying the more stable chair conf ormation of a 6-atom ring
              Understanding the stereochemical relationship between pairs of substituted cyclohexanes
              Naming and drawing linear alkenes with one double bond
              Interpreting condensed chemical structures with benzene rings
              Naming benzene derivatives
              Naming and drawing enynes and dienes (no E or Z required)

     Functional Groups (22 topics)
         Naming and drawing alcohols without alkyl side groups
         Naming and drawing alcohols
         Naming and drawing thiols without alkyl side groups
         Identif ying primary, secondary, and tertiary alcohols
         Identif ying common alcohols f rom a description
         Understanding the common names of simple ethers
         Understanding the common names of simple ketones
         Naming and drawing ketones
         Naming and drawing aldehydes
         Identif ying and drawing hemiacetals and acetals
         Understanding the common names of simple amines
         Identif ying primary, secondary, and tertiary amines
         Naming and drawing primary amines without alkyl side groups
         Naming and drawing secondary and tertiary amines
         Naming and drawing carboxylic acids
         Understanding the names of carboxylate salts
         Naming and drawing unsubstituted esters
         Identif ying primary, secondary, and tertiary amides
         Naming and drawing unsubstituted amides
         Understanding common names of carboxylic acids and derivatives
         Identif ying positions labeled with Greek letters in acids and derivatives
         Knowing the common names of small diacids

     Stereochemistry (16 topics)
          Identif ying rigid parts of an acyclic organic molecule
          Identif ying bonds with restricted rotation
          Identif ying cis/trans isomerism in a small condensed structure
          Identif ying cis/trans isomerism in a skeletal structure
          Drawing the cis or trans isomer of a small alkene
          Using Cahn-Ingold-Prelog priority rules f or alkenes
          Assigning E and Z labels to simple alkenes
          Naming and drawing cis- and trans-disubstituted cycloalkanes
          Identif ying a chiral molecule f rom its condensed structure
          Identif ying chiral centers in an acyclic organic molecule
          Identif ying chiral centers in a cyclic molecule
          Drawing the mirror image of a simple organic molecule
          Identif ying the enantiomer of a simple organic molecule
          Using Cahn-Ingold-Prelog priority rules f or small organic molecules
          Assigning R and S labels to small acyclic molecules
          Assigning R and S labels to small cyclic molecules
     Spectroscopy (5 topics)
         Understanding terms used to describe NMR spectra
         Converting chemical shif t to absorption f requency
         Identif ying the protons with unique NMR signals in a simple molecule
         Identif ying the protons with unique NMR signals in a molecule with a double bond
         Identif ying the protons with unique NMR signals in a molecule with a ring

     Organic Reactions and Mechanisms (15 topics)
         Classif ying organic reactions
         Recognizing substitution, addition, elimination, reduction, and oxidation in organic reactions
         Interpreting the components of organic reaction equations
         Identif ying nucleophiles and electrophiles in a reaction mechanism
         Using a model reaction to predict the product f or a similar reaction
         Using the Hammond Postulate to predict the starting material or products of a reaction
         Identif ying possible mechanisms f or a reaction using a reaction coordinate diagram
         Identif ying bond changes in Lewis structures f or an organic reaction
         Identif ying bond changes in skeletal structures f or an organic reaction
         Determining the product of a reaction mechanism that shows a sigma bond change at an explicit atom
         Drawing the mechanism f or a reaction that shows a sigma bonding change with partially condensed Lewis structures
         Drawing the mechanism f or a reaction that shows multiple bonding changes with partially condensed Lewis structures
         Determining the product of a reaction mechanism drawn with skeletal structures

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Drawing a mechanism on skeletal structures f or a reaction with no implicit bond changes
              Drawing the mechanism f or an acid base reaction involving an implicit hydrogen atom

     Substitution Reactions (15 topics)
         Naming and drawing alkyl halides
         Identif ying primary, secondary, and tertiary alkyl halides
         Identif ying electrophilic carbons in an alkyl halide
         Identif ying the important roles in a nucleophilic substitution reaction
         Predicting the product of a nucleophilic substitution reaction
         Comparing leaving group ability and nucleophilicity in substitution reactions
         Drawing the steps f or an SN2 or SN1 mechanism
         Drawing an SN1 mechanism including deprotonation
         Understanding the stereoselectivity of a nucleophilic substitution reaction
         Understanding how nucleophile strength impacts the mechanism in a substitution reaction
         Understanding how the degree of substrate substitution influences the mechanism of substitution
         Identif ying resonance stabilized carbocation intermediates in substitution reactions
         Predicting the eff ect of carbocation stability on the rate of reactivity
         Predicting the correct substitution products f or the reaction conditions.
         Drawing the correct substitution mechanism f or the reaction conditions.

     Elimination Reactions (12 topics)
           Identif ying beta hydrogens
           Identif ying the important roles in an elimination reaction
           Predicting the product of an elimination reaction
           Recognizing regiochemistry in elimination reactions
           Predicting major and minor elimination products
           Drawing the steps f or an E2 or E1 mechanism
           Understanding how the degree of substrate substitution influences the mechanism of elimination
           Understanding how the base influences the mechanism and products of elimination
           Recognizing the anti-periplanar requirement f or E2 elimination
           Predicting the correct elimination products f or the reaction conditions.
           Drawing the correct elimination mechanism f or the reaction conditions
           Predicting the major products when both substitution and elimination are possible

     Applications of Substitution and Elimination (10 topics)
          Predicting the products of symmetric alcohol dehydration
          Drawing the mechanism of the reaction of HX and an alcohol
          Drawing the mechanism of HX addition to an alcohol with a shif t
          Drawing the mechanism of acid-catalyzed alcohol dehydration
          Using alcohol dehydration to synthesize an alkene
          Preparing an alkyl halide f rom an alcohol in one step
          Using substitution and elimination on alcohols via tosylates
          Preparing an acyclic ether f rom an alcohol in two steps
          Predicting the products of nucleophilic epoxide ring opening
          Predicting the products of acetylide ion additions

     Electrophilic Addition Reactions (21 topics)
          Recognizing common alkene addition reactions
          Recognizing regiochemistry in HX or H2O alkene addition
          Inf erring an HX or H2O alkene addition f rom its products
          Recognizing when alkene addition creates chiral centers
          Recognizing syn and anti alkene addition
          Drawing the first step in the mechanism f or acid-catalyzed alkene addition
          Drawing the ionic mechanism f or HX alkene addition
          Drawing the mechanism f or acid-catalyzed alkene hydration
          Drawing the mechanism f or H2O or HX alkene addition with a shif t
          Predicting the products of HX alkene addition with stereochemistry
          Predicting the products of alkene hydration via acid catalysis or hydroboration-oxidation
          Fixing mistakes in an H2O or HX alkene addition reaction
          Predicting the products of alkene hydration via oxymercuration-demercuration
          Predicting the products of alkene halogenation with stereochemistry
          Predicting the products of alkene halohydrin f ormation with stereochemistry
          Predicting the reactants or products of alkene hydration
          Designing two-step syntheses using addition, elimination, and substitution reactions
          Predicting the products of alkyne halogenation or hydrohalogenation
          Recognizing keto-enol tautomerization
          Drawing the mechanism f or keto-enol tautomerization
          Predicting the products of alkyne hydration

     Organic Oxidation and Reduction (16 topics)
         Deducing oxidation state f rom a Lewis structure
         Identif ying oxidation and reduction in organic reactions
         Ranking relative oxidation or reduction f or a set organic molecules
         Predicting the reactants or products of alkene hydrogenation

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Predicting the reactants or products of carbonyl reduction
              Predicting the products of alkene hydrogenation with stereochemistry
              Predicting the products of alkyne hydrogenation
              Choosing reagents f or the reduction of ketones and aldehydes
              Predicting the reactants or products of carbonyl reduction using metal hydride reagents
              Predicting the reactants or products of nitrile reduction
              Predicting the products of alkene dihydroxylation
              Predicting the products of alkene ozonolysis
              Predicting the reactants or products of alcohol oxidation
              Predicting the reactants or products of alcohol and aldehyde oxidation
              Choosing reagents f or the oxidation of an alcohol
              Predicting the products of alkene epoxidation

     Radical Reactions (4 topics)
          Ranking the stability of hydrocarbon radicals
          Predicting the mechanism and products of a radical reaction step
          Predicting the products of alkane halogenation
          Predicting the products of allylic bromination

     Conjugated Pi Systems (14 topics)
          Identif ying conjugated double bonds
          Identif ying where a conjugated alkene may be protonated
          Predicting the products of electrophilic addition to conjugated alkenes
          Predicting the products of simple Diels-Alder reactions
          Predicting the products of a Diels-Alder reaction with a cyclic diene
          Deducing the reactants of a Diels-Alder reaction
          Using the Huckel Rule to Identif y Aromaticity
          Predicting the products of benzene halogenation, nitration, and sulf onation
          Predicting the products of Friedel‑Craf ts alkylation or acylation
          Using Friedel-Craf ts reactions f or synthesis
          Identif ying electron-donating and electron-withdrawing eff ects on benzene
          Understanding how substituents activate or deactivate a benzene ring
          Understanding directing eff ects in electrophilic aromatic substitution
          Predicting the products of electrophilic aromatic substitution with multiple directing groups
     Carbonyl Chemistry (39 topics)
         Drawing the mechanism of aldehyde or ketone hydration
         Predicting the reactants or products of hemiacetal and acetal f ormation
         Drawing the mechanism of hemiacetal f ormation
         Drawing the mechanism of acetal f ormation
         Predicting the reactants or products of acetal hydrolysis
         Drawing the mechanism of acetal or hemiacetal hydrolysis
         Predicting the products of cyclic acetal and hemiacetal f ormation or hydrolysis
         Choosing reagents and conditions f or acetal f ormation or hydrolysis
         Predicting the reactants or products of an imine or enamine f ormation reaction
         Choosing reagants f or a Wittig reaction
         Predicting the reactants or products of reductive amination.
         Predicting the products of organometallic additions to aldehydes and ketones
         Predicting the products of organometallic substitution with carboxylic acid derivatives
         Determining how mild and strong organometallic reagents react with carbonyl compounds
         Predicting the reactants or products of esterification
         Predicting the reactants or products of ester hydrolysis
         Predicting the products of ester saponification
         Predicting the reactants or products of amidation
         Predicting the products of amide hydrolysis
         Drawing the mechanism f or Fischer esterification
         Predicting the relative rates of generic nucleophilic acyl substitution reactions
         Predicting the products or reactants f or the nucleophilic acyl substitution of an acid chloride
         Drawing the mechanism f or the nucleophilic acyl substitution of an acid chloride
         Choosing conditions f or the transf ormation of a carboxylic acid to a carboxylic acid derivative
         Predicting the reactants or products of nitrile hydrolysis
         Identif ying acidic alpha H atoms in ketones, aldehydes, and esters
         Identif ying acidic alpha H atoms in 1,3-dicarbonyl and related compounds
         Drawing the mechanism of enol halogenation
         Predicting the products of enolate alkylation
         Understanding the steps of an acetoacetic ester synthesis
         Understanding the steps of a malonic ester synthesis
         Drawing the mechanism f or an aldol addition
         Predicting the products or reactants of an aldol condensation
         Predicting the product or reactant of an intramolecular aldol condensation
         Drawing the mechanism f or the first step of a Claisen condensation
         Predicting the products or reactants of a Claisen condensation
         Predicting the product or reactant of a Dieckmann condensation
         Predicting whether a carbon nucleophile adds 1,2 or 1,4 to a carbonyl or nitrile

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Predicting the products or reactants of a Michael addition
     Carbohydrates (19 topics)
         Understanding the descriptive vocabulary of monosaccharides
         Drawing the Fischer projection of the enantiomer of a monosaccharide
         Drawing the Haworth projection of an aldose f rom its Fischer projection
         Drawing the Haworth projection of a ketose f rom its Fischer projection
         Naming and drawing cyclic monosaccharides
         Identif ying a given carbon in a cyclic monosaccharide
         Naming and drawing the products of aldose oxidation and reduction
         Identif ying the parts of a disaccharide
         Knowing the names and properties of common sugars
         Identif ying common polysaccharides
         Understanding the glycosidic links in common polysaccharides
         Knowing inputs and outputs of glycolysis
         Completing a simplified diagram of glycolysis
         Completing a simplified diagram of glucose catabolism
         Solving carbohydrate catabolic stoichiometry problems
         Understanding the biochemistry of digestion
         Knowing inputs and outputs of the citric acid cycle
         Understanding the general mechanism of oxidative phosphorylation
         Solving citric acid cycle ATP stoichiometry problems

     Lipids (17 topics)
          Understanding the basic descriptive vocabulary of f atty acids
          Understanding lipid number notation
          Understanding melting points trends of f atty acids
          Identif ying the components of wax esters
          Identif ying the parts of a triacylglycerol
          Identif ying the parts of a glycerophospholipid
          Identif ying the parts of a sphingomyelin
          Identif ying molecules that could be in a cell membrane
          Recognizing the steroid nucleus
          Classif ying lipids derived f rom f atty acids
          Matching structure and f unction of common lipids
          Predicting the products or reactants of triacylglycerol hydrogenation
          Predicting the products or reactants of triacylglycerol hydrolysis or saponification
          Knowing the steps of beta oxidation
          Predicting the product of beta oxidation activation
          Knowing inputs and outputs of beta oxidation
          Solving f atty acid catabolic stoichiometry problems
     Proteins (22 topics)
          Recognizing alpha amino acids
          Classif ying amino acids
          Identif ying the stereochemistry of natural amino acids
          Understanding the general acid-base properties of amino acids
          Identif ying and drawing peptide bonds
          Describing peptides with 3-letter codes
          Identif ying specific interactions between residues in a protein
          Predicting the location in a protein of a residue sequence
          Naming an element of protein secondary structure f rom a description
          Identif ying changes at diff erent levels of protein structure
          Predicting reactants or products of phosphorylation
          Predicting the products of phosphoester or phosphoanhydride hydrolysis
          Understanding major biochemical energy storage and release reactions
          Understanding the f ormation and hydrolysis of acyl-CoA
          Knowing basic f acts about enzymes
          Classif ying enzymes
          Identif ying common redox coenzymes by their roles in a reaction
          Identif ying reactants and products f rom an enzyme name
          Understanding basic models of competitive and noncompetitive inhibition
          Predicting the eff ect of temperature or pH on enzyme activity
          Predicting the products of catabolic amino acid transamination
          Completing a diagram of protein catabolism

     Nucleic Acids (12 topics)
         Recognizing nucleotides
         Numbering the carbons in nucleotides
         Naming and drawing nucleosides
         Naming and drawing nucleotides
         Understanding the arrangement of hydrogen bonds in DNA base pairs
         Understanding the structure of nucleic acid strands
         Writing complementary DNA sequences

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Understanding that DNA replication is semiconservative
            Identif ying the major types of RNA f rom a description
            Understanding the relationship between DNA and mRNA base sequences
            Using the genetic code
            Classif ying mutations

*Other Topics Available By def ault, these topics are NOT included in the course, but can be added using the content editor in
the Teacher Module.

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