Chapter 1

1. To be able to relate chemical formulas to chemical structures
2. To be able to convert condensed structural formulas to Lewis structure formulas.
3. To be able to represent Lewis structures of organic molecules as line drawings.
4. To be able to define and recognize constitutional isomers of an organic structure.
5. Definitions of both Lewis and Bronsted/Lowry acids/bases.
6. To understand the basic meanings of arrows in interpreting electron movement.
7. To understand the relationship of Ka and pKa to each other and to a compounds acid properties.
8. To understand the relationship of free energy and Ka (or pKa) and to be able to predict from these values which direction an equilibrium will lie.
9. To be able to predict the products of acid base reactions using pKa values.
10. To understand the factors that influence acidity including resonance, the inductive effect, and general periodic trends.
11. To be able to recognize common organic bases including amines, carbanions and oxygen containing molecules.
12. To be able to understnad the factors that influence basicity including resonance, the inductive effect and general periodic trends.

1. To be able to describe the orbitals used in forming both C-C and C-H bonds in alkanes
2. To be able to identify the types of bonds (sigma vs pi) in alkanes.
3. To be able to describe the hybridzation, shape and angles around individual carbon atoms in alkanes.
4. To be able to draw a representation of a tetrahedron on paper.
5. To be be able to draw the different constitutional isomers of a given molecular formula.
6. To be able to recognize and identify primary, secondary, and tertiary carbon and hydrogen atoms.
7. To be able to recognize identical hydrogen or carbon atoms in a molecule.
8. To be able to calculate the number of unsaturations in a molecule given the molecular formula.
9. To be able to use IUPAC rules to provide a proper name for an alkane.
10. To be able to draw the structure of an alkane given the correct IUPAC name.
11. To be able to recognize the alkyl groups derived from methane, ethane, propane and the two butane constitutional isomers.
12. To recognize and name cycloalkanes
13. To understand the basic trends in the physical properties of alkanes.
14. To be able to recognize and name the basic functional groups in organic chemistry
15. To be able to describe the orbitals used in forming the bonds in the various functional groups.
16. To be able to identify the types of bonds in the various functional groups.
17. To be able to describe the hybridization, shape and angles around the different atoms in functional groups.

Chapter 3

1. To be able to define conformation.
2. To be able to depict differnent conformations of ethane, butane and other alkanes as three-dimensional drawings and Newman projections.
3. To be able to identify staggered and eclipsed conformations of alkanes and rank these in terms of energy.
4. To be able to identify anti and gauche staggered conformations of alkanes.
5. To be able to depict the energy of different alkane conformations as a function of the angle of rotation graphically.
6. To be able to identify the both torsional strain and steric hinderance in alkane conformations.
7. To be able to depict the most stable conformations of cyclopentane, cyclobutane and cyclohexane.
8. To be able to recognize molecules that possess ring strain.
9. To be able to identify the causes of ring strain.
10. To be able to clearly depict the chair conformation of cyclohexane and clearly identify axial and equatorial hydrogens.
11. To be able to clearly depict the ring flip of one chair cyclohexane conformation to another chair cyclohexane conformation.
12. To be able to explain the stability of the chair form of cyclohexane and the relative instability of the boat form.
13. To be able to clearly depict the two chair conformations of mono and disubstituted cyclohexanes and clearly identify axial and equatorial substituents.
14. To be able to analyze the two chair conformations of mono and disubstituted cyclohexanes for the lowest energy conformation.

Chapter 7

1. To be able to categorize different molecules as isomers or different, constitutional or stereoisomers, configurational or conformational isomers and enantiomers or diastereomers.
2. To be able to determine if an object (or molecule) is chiral.
3. To be able to identify a plane of symmetry or a stereocenter in a molecule.
4. To understand that enantiomers have identical physical properties except for their interaction with other chiral objects or materials.
5. To understand the interaction of chiral materials with plane polarized light and the definition of optical activity.
6. To be able to calculate the specific rotation of a given chiral molecule.
7. To understand the definition of racemic mixture and enantiomeric excess.
8. To be able to calculate the enantiomeric excess and the actual stereoisomer composition of a mixture of enantiomers.
9. To be able to assign the absolute configuration (R or S) of a stereocenter and apply this designation to the IUPAC name of that compound.
10. To be able to calculate the possible number of stereoisomers from the number of stereocenters in a molecule.
11. To be able to distinguish different stereoisomers as diastereomers or enantiomers.
12. To be able to identify a meso compound.
13. To understand that diastereomers are different compounds with different physical and chemical properties.
14. To be able to determine how cyclic stereoisomers are related to each other (enantiomers, diastereomers, meso compounds).
15. To be able to interpret Fisher projections of stereocenters.

Chapter 13

1. To understand the relationship between energy and both frequency and wavelenght.
2. To be familiar with the different portions of the electromagnetic spectrum including relative energies and types of transfomations.
3. To understand the basic principle of ultraviolet-visible spectroscopy.
4. To understand the effect of conjugation on absorbance of ultraviolet-visible light
5. To understand the basic principles of infrared spectroscopy (model of a chemical bond as two weights attached by spring).
6. To be able to distinguish areas of the infrared spectrum useful for functional group identification vs. the Fingerprint region.
7. To know the basic predictions of absorption of infrared light based on bond strenght, dipoles and weights of atoms.
8. To know the general areas of absorption in the infrared spectrum for common organic functional groups.
9. To understand the effects of conjugation on the absorption of infrared light by carbonyl bonds.
10. To be able to propose a reasonable molecular structure from a molecular formula and an infrared spectra.
11. To be able to predict whether a certain nucleus will give rise to an NMR spectra
12. To understand the basic principle of radio wave absorption by nuclei and NMR spectroscopy.
13. To understand the difference in energy of the states is proportional to the strength of the applied magnetic field.
14. To be able to convert frequency (given the frequency of the external maget) to delta (ppm).
15. To realize that proton NMR spectroscopy indicates the number of chemically unique protons in a molecule.
16. To understand that integration gives the relative number of each type of proton.
17. To understand that the chemical shift of a resonance provides information regarding the electronic environment of a proton.
18. To understand that electrons shield the nucleus from the external magentic field. Thus, "deshielded" nuclei experience a greater external field and require more energy to resonate and appear "downfield". The opposite occurs for "shielded" nuclei.
19. To understand the concept of magnetic anisotropy.
20. To be familiar with the general chemical shifts of typical protons in organic molecules as a result of both electronegativity and magnetic anisotropy.
21. To understand the basis of spin-spin coupling in proton NMR.
22. To be able to predict how a resonance will appear (be split) depending on the number of neighboring protons.
23. To be able to recognize common proton NMR splitting patterns.
24. To understand that carbon NMR gives the number of chemically different carbons, information on electronic environment and the number of attached hydrogens, but not integration.
25. To understand the meaning of a "proton-decoupled" carbon NMR spectrum.
26. To be able to predict the structure of a molecule given its molecular formula, IR and NMR spectra.
27. To be able to predict the IR and NMR spectra of a given molecule.

Chapters 4 and 8

1. To be able to classify alkyl halides and alcohols as primary, secondary or tertiary.
2. To be able to name alkyl halides and alcohols.
3. To know the common methods for conversion of alcohols to alkyl halides.
4. To be able to identify the nucleophile, electrophile and leaving group in a nucleophilic substitution reaction.
5. To be able to identify new bonds produced in a nucleophilic substitution reaction.
6. To be able to use acid-base chemistry to suggest a base to convert a neutral nucleophile to its anion.
7. To understand the trends that influence nucleophilicity.
8. To be able to define a polar aprotic solvent.
9. To be able to recognize good leaving groups.
10. To understanding the mechanism of the Sn2 reaction including the structure of the transition state, the reaction coordinate, the kinetics and stereochemistry.
11. To understanding the mechanism of the Sn1 reaction including the structure of the intemediate carbocations, the reaction coordinate, the kinetics and stereochemistry.
12. To know what types of alkyl halides tend to undergo Sn1 vs Sn2 reactions.
13. To be able to judge the stability of a carbocation.
14. To be able to recognize a carbocation rearrangement and to be able to propose an arrow pushing mechanism to explain the products.
15. To understand methods for converting alchols to better leaving groups (acid-base chemistry) and tosylate formation.

Chapter 5

1. To be able to correctly name alkenes including stereochemistry
2. To be able to identify the allyl and vinyl groups.
3. To be able to rank alkenes according to stability.
4. To be able to define and recognize an elimination reaction.
5. To understand the mechanim of the E1 reaction including the structure of the intermediate carbocation, the reaction coordinate, the kinetics and stereochemistry.
6. To be able to recognize carbocation rearrangements during E1 reactions.
7. To understand the mechanism of the E2 reaction including the structure of the transition state, the reaction coordinate, the kinetics and stereochemistry.
8. To be able to predict the products of an E2 reaction in a cyclic compound.
9. To be able to judge the most likely reaction pathway (SN1, SN2, E1, E2) of given the structure of the alkyl halide and the reaction conditions.

Chapter 6

1. To be able to show how a catalyst effects the reaction coordinate of a reaction.
2. To be able to predict the products of a catalytic hydrogenation of an alkene.
3. To be able to predict the products of the addition of H-X to an alkene (Markovnikov's rule).
4. To be able to predict the products of addition of water to an alkene.
5. To be able to predict the products of the dehydration of an alchol.
6. To be able to draw electron pushing mechanisms for each of these reactions.
7. To be able to predict the products of an oxymercuration of an alkene.
8. To be able to predict the products of the addition of borane to alkene.
9. To understand the mechanism of borane addition to an alkene.
10. To be able to predict the products and draw a mechanism for the oxidation of an organoborane.
11. To be able to predict the products of the addition of borane to an alkene followed by oxidation.
12. To be able to predict the the products of the addition of H-X to an alkene in the presence of a radical initiator.
13. To understand the three basic steps of radical chain reactions.
14. To be able to predict the product and draw a mechanism for the addition of halogens to an alkene.
15. To be able to predict that correct stereoisomers formed from the addition of halogens to symmetric and asymmetric alkenes.
16. To be able to predict and draw a mechanism for the addition of water and a halogen to an alkene (halohydrin formation).
17. To be able to predict (including stereoisomers) the epoxide products for the addition of a peroxyacid to an alkene.
18. To be able to predict the products resulting from the ozonolysis of an alkene under both oxidative and reductive conditions.
19. To be able to predict the products of the reaction of potassium permanganate or osmium tetroxide with an alkene.

Chapter 9

1. To be able to describe the bonding and hybrization in alkynes.
2. To be able to correctly name alkynes.
3. To understand the acid/base properties of alkynes and be able to predict their reactions with acids and bases.
4. To be able to use alkyne anions as nucleophiles to generate more complex carbon frameworks.
5. To be able to use alkyne chemistry in the synthesis of organic molecules.
6. To be able to predict the products of the hydrogenation of an alkyne.
7. To be able to predict the product of the metal reduction of an alkyne.
8. To be able to predict the product of the addition of H-X to alkynes.
9. To be able to predict the product and depict a mechanism for the acidic hydration of an alkyne.
10. To be able to recognize an enol and draw a mechanism for the converion to the ketone form.
11. To be able to predict the reactions of ozone with alkynes.