Learning Targets

Course Goal 1

I can clearly communicate the structure and properties of organic molecules using common drawing and naming conventions.

LT1.1 Lewis structures and bonding CORE

• I can describe properties of an atom (hybridization, geometry, number of non-bonding electron pairs, partial charge, formal charge)
• I can identify the main characteristics of a given bond (type, angle, polarization)
• I can interconvert between different drawing styles (Lewis dot structures, bond–line/zig–zag structures, condensed formulas, and composition formulas)
• I can draw a complete Lewis structure of organic molecules

LT1.2 Basic nomenclature CORE

• I can draw a molecule representative of a given functional group
• I can and use basic IUPAC nomenclature rules to convert structure to name
• I can and use basic IUPAC nomenclature rules to convert name to structure (simple alkanes, cycloalkanes, and alkyl halides).
• Identify functional groups that can participate in intermolecular bonding interactions
• I can describe the basic nature of all intermolecular forces and how they affect basic physicochemical properties

LT1.3 Electron delocalization and basic arrow pushing CORE

• I can identify areas in a molecule where resonance applies
• I can use MO theory to illustrate electron delocalization in the allyl-type system
• I can draw valid resonance contributors and assess their relative importance
• I can use electron-pushing arrows to interconvert between resonance structures
• I can classify a bond (or lone pair) as localized or delocalized

LT1.4 Stereochemistry CORE

• I can identify all types of (stereo)isomeric relationship (or lack thereof) between two molecules
• I can identify chirality centers and assign absolute configuration
• I can predict if a liquid sample of an organic compound will rotate the plane of polarized light
• I can communicate enantiomeric enrichment using specific rotation, %ee, and er
• I can interconvert between Fisher projection and bond–line structures

LT1.5 Advanced nomenclature

• I can draw a molecule given its common name
• I can use IUPAC nomenclature rules to convert structure to name and name to structure (alkanes, alkenes, alkynes, halides, alcohols, ethers).
• I can calculate the degree of unsaturation
• I can draw a representative molecule with given constraints.

Course Goal 2

I can analyze chemical structures and reactions to make and defend predictions about chemical processes

LT2.1 Acid–base reactions CORE

• I can identify and label the components of a acid–base reaction
• I can use cureved arrows to illustrate electron flow in an acid–base reaction
• I am able to asses relative acidity and basicity of organic molecules by means of pKa
• I am able to asses relative acidity and basicity of organic molecules by analyzing the stability of their conjugate bases
• I can predict the direction of the acid–base equilibrium for a given reaction

LT2.2 Molecular conformations

• I can draw different projections of conformations of acyclic molecules (wedge/dash, sawhorse, Newman projections)
• I can assess the relative energy of conformations
• I can draw a chair conformation of substituted cyclohexane and it’s flipped conformer, and label substituents as axial and equatorial
• I can assess the relative energy of chair conformations to predict the position of ring flip equilibrium.

LT2.3 Communicating reactivity CORE

• I can recognize nucleophilic and electrophilic sites in organic molecules
• I can identify the elementary reaction steps given the reaction and curved arrows
• I can describe the relationship between structure and stability of reactive intermediates (carbocations, carbanions, radicals)
• I can use curved arrows to show how bonds form and break in an ionic (2-electron) reaction
• I can use curved arrows to show how bonds form and break in a radical (1-electron) reaction

LT2.4 Characteristics of reactions

• I can identify different categories of chemical reactions (substitution, elimination, addition)
• I can predict the sign deltaH, deltaS, and deltaG for a given reaction
• I can deconstruct energy diagrams to extract relevant information about a chemical reaction
• I can draw an energy diagram of a reaction with specified parameters
• I can explain how different factors (temperature, sterics, catalysts) affect the reaction rate

LT2.5 Chemistry of free radicals

• I can describe the key parts of the radical chain reaction mechanism
• I can discriminate between common patterns in radical reactions
• I can use thermodynamic and kinetic analysis to explain and predict the regiochemistry of radical halogenation of alkanes
• I can use curved arrows to communicate electron flow in a radical reaction
• I can propose a selective synthesis of an alkyl halide using a radical reaction

LT2.6 Substitution

• I can identify a substitution reaction among other classes of reactions
• I can draw a TS and a complete mechanism of a given an SN1 and SN2 process
• I can complete a reaction scheme in which one component (reactant, reagents & conditions, or products) is missing
• I can predict which mechanism will dominate given the reactants and reaction conditions
• I can make predictions about the stereochemistry of reactants or products in simple nucleophilic substitution reactions

LT2.7 Elimination

• I can identify an elimination reaction among other classes of reactions
• I can draw a TS and a complete mechanism of a given E1 and E2 process
• I can complete a reaction scheme in which one component (reactant, reagents & conditions, or products) is missing
• I can predict which mechanism will dominate given the reactants and reaction conditions
• I can recognize the kinetic and thermodynamic product of elimination
• I can analyze reaction conditions and predict product(s) in cases where both substitution and elimination is possible

LT2.8 Reactions of alkenes

• I can identify an addition reaction among other classes of reactions
• I can evaluate and complete a reaction scheme in which one of the components (reactant, reagents & conditions, or products) is missing
• I can predict and defend the regioselectivity of additions to alkenes
• I can propose an addition–elimination sequence to transpose the double bond in an alkene

LT2.9 Reactions of alkynes

• I can identify an addition to alkynes among other classes of reactions
• I can identify a deprotonation reaction of alkynes
• I can identify a C–C bond forming reaction
• I can evaluate and complete a reaction scheme in which one of the components (reactant, reagents & conditions, or products) is missing for reactions that involve alkynes
• I can predict and defend the regioselectivity of additions to alkynes

LT2.10 Stereochemistry in reactions

• I can predict and defend the stereoselectivity of additions to alkenes
• I can predict and defend the stereoselectivity of additions to alkynes
• I can predict whether the product of a reaction will be optically active or not

LT2.11 Synthesis of complex molecules

• I can develop a synthetic strategy using retrosynthetic analysis
• I can identify problems in a flawed multitep synthesis
• I can propose and defend a plausible synthesis of a molecule given constraints
• I can complete a multistep synthesis scheme in which structures or reaction conditions are missing