FARMINGDALE STATE COLLEGEDEPARTMENT OF CHEMISTRY

COURSE OUTLINE: Prepared by Dr. Victor HuangSeptember 2016

COURSE TITLE: Fundamentals of Organic Chemistry

COURSE CODE: CHM 260

CREDITS: 4

CONTACT HOURS: Lecture: 3 Laboratory: 3

CATALOG DESCRIPTION: A one-semester course in organic chemistry designed to provide background in the fundamentals of nomenclature,mechanisms, structures, and synthesis of carbon-basedcompounds. This course is designed for science and healthscience majors who desire a general rather than a detailedknowledge of the compounds of carbon. Topics to be coveredinclude: structure and bonding; acid/base chemistry; stereo-chemistry. Functional groups to be covered include: hydro-carbons, alcohols, ethers, aldehydes and ketones,carboxylic acids, carboxylic acid derivatives, and amines.Laboratory work will include common organic techniquesand experiments supporting the principles covered in lecture.

PREREQUISITE: CHM 153

IMPORTANT NOTE: BOTH THEORY AND LABORATORY PARTS OF THISCOURSE MUST BE TAKEN CONCURRENTLY IN ORDERTO RECEIVE CREDIT.

REQUIRED FOR: Bioscience; Medical Laboratory Technology

RECOMMENDED TEXT: Fundamentals of Organic Chemistry, 7th Edition; McMurry;Brooks/Cole publishers.

OPTIONAL TEXT: None

REQUIRED SUPPLIES: Laboratory coat and safety goggles. Other equipment may berequired by the instructor.

FARMINGDALE STATE COLLEGEDEPARTMENT OF CHEMISTRY

CHM 260 – Fundamentals of Organic Chemistry

Lecture Schedule

Learning objectives are listed after each section below:

1. Review of structure/bonding; Alkanes

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

Section 1 – 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 withmutiple 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 strucutures of common organic compounds, such as: alkenes,alkynes, alcohols, phenols, ethers, aldehydes, ketones, amines, amides, arenes, andcarboxylic acids based on their functional groups.13. Name alkanes (linear and cyclic) based on their structure; draw alkanes based ontheir names.14. Draw Newman projections for linear alkanes; identify least and most favorableconformations.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 leastand most favorable conformations.

2. 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.

Section 2 – 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 ontheir 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 electro-phile; 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

3. Resonance; Aromatic Compounds; Stereochemistry

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

Section 3 – At the end of this section, the student should be able to:

1. Draw resonance structures of cationic and anionic compounds2. Use resonance to predict products of electrophilic addition reactions with conjugatedalkenes.3. Name aromatic hydrocarbons from their structures; draw aromatic hydrocarbons fromtheir names.4. Understand the mechanism and predict the products of the following electrophilicaromatic substitution reactions...

- halogenation- nitration- Friedel-Crafts alkylation- Friedel-Crafts acylation

5. Predict the products of aromatic sidechain oxidation.6. Understand the effects of electron-donating and electron-withdrawing groups onelectrophilic aromatic substitution reactions. Predict the products of electrophilicaromatic substitution reactions starting with monosubstituted benezenes.7. Use the five aromatic reactions to propose syntheses of simple aromatic compounds.8. Recognize chiral vs achiral centers.9. Assign R or S configurations to chiral centers.10. Understand the concept of optical activity. Know the relationship between opticalactivity in enantiomers.11. Diastereomers of compounds with 2 stereocenters... given one configurationdetermine the configuration of the enantiomer and the two diastereomers; predict theoptical activity of the enantiomer based on the optical activity of the original compound12. Know the stereochemical preference of naturally occurring amino acids and sugars.

4. Alcohols and Related Compounds; Aldehydes and Ketones

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

Section 4 – 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 fromtheir names.7. Predict the products of reduction of aldehydes or ketones.8. Predict the products of nucleophilic addition to aldehydes/ketones under acidic orbasic conditions.9. Understand how hemiacetals and acetals form. Predict the products of hemiacetal oracetal reactions.10. Predict the products of Grignard reactions with aldehydes/ketones.11. Use alcohol and aldehyde/ketone reactions to propose syntheses of simplecompounds using alcohols and aldehyde/ketones as starting material.12. Predict products of keto-enol tautomerization.

5. Carboxylic Acids and Derivatives; Amines

General characteristics of carboxylic acids. Nomenclature of carboxylic acids and theirderivatives (acid halides; anhydrides; esters; amides). Acid/base equilibrium. Reactionsof carboxylic acids and their derivatives. General characteristics of amines. Nomen-clature of amines. Reactions of amines.

Section 5 – 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 ontheir name.2. Write chemical equations for the equilibrium of carboxylic acids and amines inaqueous 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 con-jugate bases; use Kb and pKb values to assess relative strengths of amines and theirconjugate 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 theirderivatives with...

- water- alcohols

- amines- reducing agent

7. Name amines based on their structures; draw amines from their name.8. Predict the products of amide reduction.9. Propose syntheses of simple compounds using carboxylic acids/derivatives andamines as the starting material.

FARMINGDALE STATE COLLEGEDEPARTMENT OF CHEMISTRY

CHM 260 – Fundamentals of Organic Chemistry

Laboratory Schedule

Lab Period Experiment

1 Check-in/Safety2 Melting Points3 Recrystallization4 Distillation5 Extraction of a 3-Component Mixture (Acid/Base/Neutral)6 Synthesis of t-Butyl Chloride7 Synthesis of Cyclohexene8 Gas Chromatography9 Reactions of Alcohols: Identification of Unknown Alcohol10 Synthesis of Benzhydrol11 Reactions of Aldehydes/Ketones: Identification of Unknown Carbonyl12 Synthesis of Aspirin13 Synthesis of Benzoic Acid14 Check-out