Course Outline: Fundamentals of Organic Chemistry (CHM260)

Credits: 4
Contact Hours:
Lecture: 3
Lab: 3
NOTE on Laboratory: Both Lecture and Laboratory must be taken simultaneously; separate grades will not be given for either. Students must pass the laboratory section to receive a passing grade in the entire course.

Semesters Offered: Fall, Spring, & Summer

Prerequisites: General Chemistry Principles II (CHM 153) or equivalent.

Catalog Course Description:

A one-semester course in organic chemistry designed to provide background in the fundamentals of nomenclature, mechanisms, structures, and synthesis of carbon-based compounds. This course is designed for science and health science majors who desire a general rather than a detailed knowledge of the compounds of carbon. Topics to be covered include: structure and bonding; acid/base chemistry; stereochemistry. Functional groups to be covered include: hydrocarbons, alcohols, ethers, aldehydes and ketones, carboxylic acids, carboxylic acid derivatives, and amines. Laboratory work will include common organic techniques and experiments supporting the principles covered in lecture.

Required Course for:           Bioscience; Medical Laboratory Technology

Elective Course for:              Science, Technology, & Society; Health Sciences Certificate

Course Texts: 

Fundamentals of Organic Chemistry (McMurry, 7th Edition, Brooks/Cole)

CHM 260 Laboratory Manual for Fundamentals of Organic Chemistry (Huang, Victor, FSC Chemistry Dept.)

Other Required Course Materials

Calculator, laboratory coat and safety goggles.

Course Learning Objectives:

I. Review of structure/bonding; Alkanes

            Definition of organic chemistry. Atomic structure. Atomic orbitals and electron configuration. Chemical bonds: ionic; covalent. Molecular and structural formulas. Use of atomic orbitals in covalent bond formation. Sigma and pi bonds. Functional groups. Alkane nomenclature. Conformational analysis of simple alkanes and cyclohexane.

 At the end of this section, the student should be able to:

  1. Understand why there are so many organic compounds.
  2. List some common elements, besides carbon, found in many organic compounds.
  3. Describe the types of orbitals found in each of the first four main energy levels.
  4. Write the electronic configuration for any of the first twenty elements.
  5. State the octet rule and understand its significance.
  6. Describe the formation of covalent bonds.
  7. Write Lewis structures for covalent molecules, including organic molecules with multiple bonds.
  8. Differentiate between molecular and structural formulas.
  9. Draw structures based on formulas; write formulas based on structures.
  10. Describe covalent bond formation using atomic orbitals of atoms.
  11. Distinguish between a sigma and a pi bond.
  12. Recognize the structures of common organic compounds, such as: alkenes, alkynes, alcohols, phenols, ethers, aldehydes, ketones, amines, amides, arenes, and carboxylic acids based on their functional groups.
  13. Name alkanes (linear and cyclic) based on their structure; draw alkanes based on their names.
  14. Draw Newman projections for linear alkanes; identify least and most favorable conformations.
  15. Draw the chair forms of cyclohexane; identify the axial and equatorial positions; know how the axial and equatorial positions change between chair forms; identify least and most favorable conformations.

II. Alkenes and Organic Reactivity

General characteristics of alkenes. Alkene nomenclature. Cis/trans isomerism. E/Z configurations.

Nature of organic reactions; electrophiles vs nucleophiles. Reaction mechanisms. Reactions of alkenes. Markovnikov's rule.

At the end of this section, the student should be able to:

  1. Name alkenes (linear and cyclic) based on their structure; draw alkenes based on their name.
  2. Recognize whether an alkene can have cis and trans isomers.
  3. Assign E or Z configuration to an alkene.
  4. Recognize electrophiles and nucleophiles.
  5. Interpret a reaction mechanism to identify the initiating nucleophile and final electrophile; predict the products based on a reaction mechanism.
  6. Predict the products of the following electrophilic addition reactions...

-  halohydrin (HX, X = F, Cl, Br, I)

-  water

-  halogen

-  hydrogenation

        7. Predict the products of halohydrin or water addition using Markovnikov's rule

III. Resonance; Aromatic Compounds; Stereochemistry

Resonance. Rules for resonance. Effect of resonance on reactivity of conjugated  alkenes. Benzene. Effect of resonance on reactivity of benzene. Aromatic nomenclature: a) systematic and common names for common aromatic hydrocarbons; b) ortho, meta, and para convention for disubstituted aromatic compounds; c) numbering convention. Aromatic reactions: halogenation; nitration; Friedel-Crafts alkylation; Friedel-Crafts acylation; aromatic sidechain oxidation. Effect of substituents on electrophilic aromatic substitution reactions. Synthesis of simple aromatic compounds. Stereochemistry. Chirality. Absolute and relative stereochemical configurations. Optical activity. Diastereomers. Stereochemistry of amino acids and sugars.

At the end of this section, the student should be able to:

  1. Draw resonance structures of cationic and anionic compound.
  2. Use resonance to predict products of electrophilic addition reactions with conjugated alkenes.
  3. Name aromatic hydrocarbons from their structures; draw aromatic hydrocarbons from their names.
  4. Understand the mechanism and predict the products of the following electrophilic aromatic substitution reactions...

-  halogenation

-  nitration

-  Friedel-Crafts alkylation

-  Friedel-Crafts acylation

  1. Predict the products of aromatic sidechain oxidation.
  2. Understand the effects of electron-donating and electron-withdrawing groups on electrophilic aromatic substitution reactions. Predict the products of electrophilic aromatic substitution reactions starting with monosubstituted benezenes.
  3. Use the five aromatic reactions to propose syntheses of simple aromatic compounds.
  4. Recognize chiral vs achiral centers.
  5. Assign R or S configurations to chiral centers.
  6. Understand the concept of optical activity. Know the relationship between optical activity in enantiomers.
  7. Diastereomers of compounds with 2 stereocenters... given one configuration determine the configuration of the enantiomer and the two diastereomers; predict the optical activity of the enantiomer based on the optical activity of the original compound
  8. Know the stereochemical preference of naturally occurring amino acids and sugars.

IV. Alcohols and Related Compounds; Aldehydes and Ketones

General characteristics of alcohols. Alcohol and ether nomenclature; thiol and sulfide nomenclature. Reactions of alcohols and thiols. Substitution vs elimination reactions. General characteristics of carbonyl compounds. Aldehyde and ketone nomenclature. Reactions of aldehydes and ketones. Ketoenol tautomerization.

At the end of this section, the student should be able to:

  1. Name alcohols/ethers/thiols/sulfides based on their structures; draw alcohols/ethers/ thiols/sulfides from their names.
  2. Predict the products of acid-catalyzed dehydration of alcohols using Zaitsev's rule.
  3. Predict the products of oxidation of primary and secondary alcohols.
  4. Predict the products of thiol oxidation.
  5. Understand the difference between elimination vs nucleophilic substitution reactions. Predict whether an alkyl halide will undergo elimination or substitution.
  6. Name aldehydes/ketones based on their structures; draw aldehydes/ketones from their names.
  7. Predict the products of reduction of aldehydes or ketones.
  8. Predict the products of nucleophilic addition to aldehydes/ketones under acidic or basic conditions.
  9. Understand how hemiacetals and acetals form. Predict the products of hemiacetal or acetal reactions.
  10. Predict the products of Grignard reactions with aldehydes/ketones.
  11. Use alcohol and aldehyde/ketone reactions to propose syntheses of simple compounds using alcohols and aldehyde/ketones as starting material.
  12. Predict products of keto-enol tautomerization.

V. Carboxylic Acids and Derivatives; Amines

General characteristics of carboxylic acids. Nomenclature of carboxylic acids and their derivatives (acid halides; anhydrides; esters; amides). Acid/base equilibrium. Reactions of carboxylic acids and their

derivatives. General characteristics of amines. Nomenclature of amines. Reactions of amines.

At the end of this section, the student should be able to:

  1. Name carboxylic acids and their derivatives (acid halides; anhydrides; esters; amides) based on their structures; draw carboxlic acids and their derivatives based on their name.
  2. Write chemical equations for the equilibrium of carboxylic acids and amines in aqueous solution. Identify acid/conjugate base pairs and base/conjugate acid pairs.
  3. Use Ka and pKa values to assess relative strengths of carboxylic acids and their conjugate bases; use Kb and pKb values to assess relative strengths of amines and their conjugate acids.
  4. Use Henderson-Hasselbach equation to understand and predict ratio of acid/conjugate base or base/conjugate acid based on pH and pKa.
  5. Understand the effects of resonance on the strengths of carboxylic acids and amines.
  6. Predict the products of nucleophilic acyl substitution of carboxylic acids and their derivatives with...

-  water

-  alcohols

-  amines

-  reducing agent

  1. Name amines based on their structures; draw amines from their name.
  2. Predict the products of amide reduction.
  3. Propose syntheses of simple compounds using carboxylic acids/derivatives and amines as the starting material.

Laboratory Schedule

Experiment                                   Title                                                                  Pages

1                                                     Check-In & Safety Lecture

2                                                     Melting Points                                                     3-9

3                                                     Recrystallization                                                10-17

4                                                     Distillation                                                          18-25

5                                                     Extraction of Three-Component Mixture            26-35

6                                                     Synthesis of t-Butyl Chloride                              36-44

7                                                     Synthesis of Cyclohexene                                  45-51

8                                                     Gas Chromatography                                         52-61

9                                                     Identification of Unknown Alcohol                      62-69

10                                                   Synthesis of Benzhydrol                                     70-73

11                                                   Identification of Unknown Carbonyl                    74-80

12                                                   Synthesis of Aspirin                                            81-86

13                                                   Synthesis of Benzoic Acid                                  87-91

14                                                   Checkout