Section 1.    -    At the end of this section, the student should be able to:

1. Predict the number of valence-shell electrons of an element.

2. Predict the electronegativity of an element.

3. Draw Lewis electron dot structures for simple compounds.

4. Draw line-bond structures for compounds.

5. Predict and describe the hybridization of bonds in organic compounds.

6. Draw organic structures with correct three-dimensional geometry.

7. Identify bonds in a molecule as ionic or covalent.

8. Predict the polarity of a bond.

9. Distinguish between a sigma and a Pi molecular orbital.

10. Identify the conjugate acid-base pairs in Bronsted-Lowry acid-base reactions.

11. Identify Lewis acids and bases.

Section II.  -  At the end of this section, the student should be able to:

1. Draw all isomers of a given alkane molecular formula.

2. Name alkanes by the IUPAC system.

3. Draw structures of alkanes corresponding to a given IUPAC name.

4. Identify carbon atoms as primary, secondary, tertiary or quarternarly.

5. Identify and draw structures of alkyl groups.

6. List methods of preparing alkanes.

7. List reactions of alkanes.

8. Write a mechanism for the halogenation of an alkane.

9.  Write a mechanism for the cracking of an alkane.

10. Apply the free radical mechanism to other compounds.

Section III. -  At the end of this section, the student should be able to:

1. Name alkenes by the IUPAC system.

2. Draw structures of alkenes corresponding to a given IUPAC name.

3. Draw all the isomers of a given alkene molecule.

4. Draw a molecular orbital picture of an alkene.

5. Differentiate between cis and trans isomers.

6.  Write chemical equations for the preparation of alkenes.

7. Write chemical equations for the reactions of alkenes.

8. Write a general mechanism for addition reactions of alkenes.

9.  Explain Markovnikov’s Rule and “the peroxide effect”.

10. Write a mechanism for Markovnikov’s addition reactions.

11. Write a mechanism for anti-Markovnikov’s addition reaction.

12. Explain how a carbanion forms.   

1. Name alkynes and dienes by the IUPAC system.
2. Draw structures of alkynes and dienes corresponding to a given IUPAC name.
3. Draw all isomers of a given alkyne molecule.
4. Draw the molecular orbital picture of a typical alkyne and diene.
5. Explain resonance and resonance energy concepts.
6. Write chemical equations for the preparation of alkynes and dienes.
7. Write chemical equations for the reactions of alkynes and dienes.
8. Explain the principle behind 1, 4 - addition reactions of dienes.
9. Propose a mechanism for 1, 4 - addition reactions.
10. Explain keto-enol tautomerization.

1. Explain the reactivity of small rings.
2. Define Baeyer, Transannular and Pitzer strains.
3. Write chemical equations for the formation of cycloalkanes.
4. Explain how carbenes are formed.
5. Explain carbene insertion reaction mechanism.
6. Describe the three dimensional shapes of cycloalkanes of five carbon atoms or less.
7. Describe the three dimensional shapes of cycloalkanes of six carbon atoms or greater.
8. Locate axial and equitorial positions on cyclohexane.
9. Identify cis and trans positions on a cyclohexane ring.
10. Write chemical equations for the formation of cycloalkenes and cycloalkynes.

1. Explain the meaning of isomer number.
2. Explain the causes of optical activity.
3. Calculate the specific rotation of a solution.
4. Decide whether objects are chiral.
5. Locate stereocenters in molecules.
   6. Draw the enantiomer of a given chiral compound.
6. Draw the diastereoisomer of a given chiral compound.
7. Apply Van't Hoff's Rule.
8. Identify racemic modifications.
9. Draw chiral molecules in Newman and Sawhorse projections.
10. Assign priorities to substituents around a carbon stereocenter.
11. Assign r,s configurations to stereocenters.
12. Decide if a stereoisomer is a meso compound.
13. Predict the stereochemistry of reaction products.

Section VII. - At the end of this section, the student should be able to:

1. Explain how molecular weights are determined via mass spectrometry.
2. Apply splitting rules to simple organic molecules.
3. Identify the functional group giving rise to specific infrared absorptions.
4. Use infrared spectroscopy to identify compounds.
5. Predict if compounds show ultraviolet absorption in the range 100 - 400 nm.
6. Predict the number of chemical shifts appearing in the HNMR spectra of compounds.
7. Explain the relationships, which exist between delta values, chemical shifts and spectrometer operating frequency.
8. Explain J - values.
9. Predict chemical shifts.
10. Use integration values of chemical shifts to calculate the number of protons giving rise to specific absorptions.
11. Predict first order splitting patterns in NMR spectra.
12. Propose structures for compounds given their NMR Spectra
13. Propose structures for complex organic molecules given their mass, infrared, ultraviolet, and nuclear magnetic resonance spectras.

Introduction to Organic Laboratory Techniques 
by Pavia, Lampman and Kriz

Lab Period

Experiment