Download CHM 260 – Fundamentals of Organic Chemistry

FARMINGDALE STATE COLLEGE
DEPARTMENT OF CHEMISTRY
COURSE OUTLINE:
Prepared by Dr. Victor Huang
September 2016
COURSE TITLE:
Fundamentals of Organic Chemistry
COURSE CODE:
CHM 260
CREDITS:
4
CONTACT HOURS:
Lecture: 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-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.
PREREQUISITE:
CHM 153
IMPORTANT NOTE:
BOTH THEORY AND LABORATORY PARTS OF THIS
COURSE MUST BE TAKEN CONCURRENTLY IN ORDER
TO 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 be
required by the instructor.
Laboratory: 3
FARMINGDALE STATE COLLEGE
DEPARTMENT 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 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.
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 with
mutiple 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, 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.
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 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
3.
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; FriedelCrafts 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.
Section 3 – At the end of this section, the student should be able to:
1. Draw resonance structures of cationic and anionic compounds
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
5. Predict the products of aromatic sidechain oxidation.
6. 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.
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 optical
activity in enantiomers.
11. 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
12. 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 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. 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 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.
5.
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.
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 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 pK a.
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
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 and
amines as the starting material.
FARMINGDALE STATE COLLEGE
DEPARTMENT OF CHEMISTRY
CHM 260 – Fundamentals of Organic Chemistry
Laboratory Schedule
Lab Period
Experiment
1
2
3
4
5
6
7
8
9
10
11
12
13
14
Check-in/Safety
Melting Points
Recrystallization
Distillation
Extraction of a 3-Component Mixture (Acid/Base/Neutral)
Synthesis of t-Butyl Chloride
Synthesis of Cyclohexene
Gas Chromatography
Reactions of Alcohols: Identification of Unknown Alcohol
Synthesis of Benzhydrol
Reactions of Aldehydes/Ketones: Identification of Unknown Carbonyl
Synthesis of Aspirin
Synthesis of Benzoic Acid
Check-out