CHEM 250 - Survey of Organic Chemistry

5 Credit: (3 lecture, 3 lab, 0 clinical) 6 Contact Hours: [CHEM 105  or CHEM 221 ]

Objectives:

1. Use and understand electron configuration and orbital diagrams.
2. Predict the hybridization of a carbon atom in different structures.
3. Differentiate between polar and non-polar substances.
4. Calculate formal charge.
5. Draw Kekule and condensed structures for various organic compounds.
6. Understand the relationship between pKa and pH.
7. Describe how pH affects the structure of an organic compound.
8. Distinguish between Lewis acids and Lewis bases.

Goal 2:  Develop an understanding for the nomenclature, physical properties, and structural representation of organic compounds.

Objectives:

1. Describe the physical characteristics of alkanes in terms of melting points, boiling points, and densities.
2. Memorize the various alkyl substituents covered in class.
3. Name and write formulas for alkanes C1 - C10.
4. Recognize and describe various functional groups, including alkyl halides, alcohols, amines, and ethers.
5. Draw an describe alkanes and cycloalkanes in various conformations.

Goal 3:  Understand the structure, nomenclature, stability, and reactivity of alkenes and alkynes.

Objectives:

1. Recognize and describe the bonding in alkenes.
2. Name and write formulas for alkenes.
3. Name various geometrical isomers using cis/trans and e/z systems.
4. Determine the relative stability of alkenes.
5. Understand the basics of how mechanisms are used in organic chemistry.
6. Predict the products of alkene and alkyne reactions.
7. Understand carbocation rearrangement through hydride or methyl shifts.
8. Devise an approach to multistep synthesis.

Goal 4:  Describe the various types of isomers.

Objectives:

1. Recognize the difference between cis and trans isomers.
2. Determine the asymmetric center of chiral molecules.
3. Differentiate between meso compounds and chiral compounds.
4. Draw and name enantiomers using the R, S system.

Goal 5:  Describe resonance effects and predict aromaticity.

Objectives:

1. Draw resonance contributors and resonance hybrids.
2. Understand stabilities of resonance structures and predict acidic or basic properties.
3. Predict aromaticity for various compounds.
4. Name and draw various monosubstituted benzenes.
5. Recite the general mechanism for electrophilic aromatic substitutions (EAS).
6. Predict the products for EAS reactions (halogenation, nitration, sulfonation, Friedel-Crafts Acylation/Alkylation).
7. Name and recognize disubstituted benzenes.
8. Recognize the effect of ortho, para directors, versus meta directors.
9. Recognize the effect of activation/deactivation substituents on reactions of substituted benzenes.

Goal 6:  Differentiate between substitution and elimination reactions of alkyl halides.

Objectives:

1. Describe kinetics, possible rearrangements, nucleophilic attack, reactivity order, leaving groups, and solvent effects for Sn1, Sn2, E1, and E2 reactions.
2. Describe the mechanisms for Sn1, Sn2, E1, and E2 reactions.
3. Determine if a particular reaction will undergo substitution, elimination, or both.

Goal 7:  Describe the reactions of alcohols, amines, ethers, and epoxides.

Objectives:

1. Name and draw structures for various alcohols and ethers.
2. Predict the products of elimination, substitution, and oxidation reactions for alcohols.
3. Predict the products of nucleophilic substitution reactions of ethers and epoxides.
4. Explain why amines do not undergo substitution or elimination reactions.

Goal 8:  Develop familiarity with the properties of carbonyl compounds.

Objectives:

1. Name and draw structures for carboxylic acids and their derivatives.
2. Differentiate between class I and class II carbonyl compounds.
3. Recite the general mechanism for nucleophilic acyl substitution and determine relative reactivities.
4. Apply the general mechanism to acyl halides, esters, carboxylic acids, and amides.
5. Explain the use of Grignard Reagents.

Goal 9:  Explain the various methods in-which the structures of organic compounds can be determined experimentally.

Objectives:

1. Describe Mass Spectrometry (MS) and identify compounds based on fragmentation patterns.
2. Describe Infrared Spectroscopy (IR) and recognize the common IR frequencies of various organic functional groups.
3. Describe Proton Nuclear Magnetic Resonance (1H NMR) Spectroscopy and identify compounds based chemical shifts and signal splitting.
4. Utilize MS, IR, and 1HNMR collectively to identify organic compounds.

Goal 10:  Become familiar with the equipment used in the organic chemistry laboratory.

Objectives:

1. Demonstrate how to properly use the melting point apparatus, thin-layer chromatography, gas chromatograph, Fourier Transform Infrared Spectrometer (FTIR), and a large variety of organic glassware.
2. Practice safe laboratory practices when working with organic chemicals.