CHM 240 - Survey of Organic Chemistry

1. Predict patterns and properties, both physical and chemical, that occur in organic chemistry related to topics such as solubility and reactivity of different classes of compounds.
2. Apply the systematic method of nomenclature to organic compounds, including assignment of chiral centers for enantiomers and diastereomers.
3. Predict the products of a variety of organic reactions, including acid/base, substitution, elimination, addition, oxidation/reduction, and nucleophilic acyl substitution.
4. Write the correct mechanisms for a variety of organic chemical reactions.
5. Design efficient multi-step syntheses using retrosynthetic analysis.
6. Discuss and preform basic organic laboratory techniques such as recrystallization, extraction, distillation and chromatography.
7. Demonstrate correct laboratory techniques, including safety, recrystallization, TLC, extraction, and distillation to study the outcomes of organic reactions.

1. Structure of the atom, electron configuration, orbitals and orbital energy level diagrams
2. Ionic bonding
3. Covalent bonding and introduction to electron pushing
4. Lewis Structures, electronegativity, bond polarity and dipoles
5. Line-angle structures
6. Covalent bond formation with carbon, hybridization, orbital illustrations bond strength and bond length
7. Hybridization of other atoms: methyl cation, methyl anion, methyl radical, oxygen and nitrogen
8. Intermolecular forces and physical properties (boiling points, melting points and solubility)
9. Functional groups

II. Alkanes

1. Acyclic and cyclic saturated hydrocarbons
2. Nomenclature of acyclic and cyclic alkanes
3. Physical properties of saturated hydrocarbons
4. Classification of atoms as quaternary, tertiary, secondary or primary: alkane carbons, alcohols, alkyl halides and amines
5. Classification of carbon with formal charges (carbocations and carbanions)
6. Isomers: Constitutional, positional and functional group
7. Halogenation of alkanes

III. Resonance

1. Resonance and its importance
2. Resonance in ozone
3. Patterns for drawing resonance
4. When to consider resonance and deciding on the best resonance contributor
5. Resonance in heteroaromatic compounds

IV. Acids and Bases

1. Bronsted/Lowry Acids and Bases
2. Mechanisms for acid-base reactions
3. Which lone pair on a base with multiple receptor site will dominate as a base
4. Pi electrons as bases
5. Quantitative approach to decide if a proton transfer will occur: pKa
6. Qualitative approach to decide if a proton transfer will: ARIO
7. Lewis Acids and Bases

V. Conformational Analysis for Alkanes and Cycloalkanes

1. Wedge-dash
2. Sawhorse
3. Newman
4. Converting between the three projections and the most stable or least stable conformer
5. Conformers of cyclohexane
6. Chair conformer and flipping the chair
7. Stabilities of chair conformers
8. Converting between wedge-dash and chair
9. Cis-trans isomers in cyclohexane
10. Cis-declin and trans-declin fused rings and their chair conformers

VI. Stereochemistry

1. Cis-trans isomers in alkenes
2. Chiral carbons
3. Cahn-Ingold Prelog System (R or S)
4. Enantiomers
5. Diastereomers
6. Meso Compounds
7. Optical Activity and measuring specific rotation
8. Separating enantiomers
9. Chirality in biochemistry

VII. Substitution and Eliminations Reactions

1. Overview of nucleophilic substitution reactions and elimination reactions
2. Nucleophiles and electrophiles and how to identify them
3. Mechanisms between nucleophiles and electrophiles – characteristic mechanistic patterns (including rearrangements)
4. Combining patterns and writing reasonable mechanisms for reactions
5. Reaction coordinate diagrams for Sn1 and Sn2
6. Rates of reactions and factors that affect rates (activation energy, temperature and sterics)
7. Substitution reactions (Sn1 vs Sn2), leaving groups and stereospecificity
8. Stereochemistry of enzyme-catalyzed reactions
9. Deciding if Sn1 or Sn2 dominate
10. Elimination reactions (E1 and E2)
11. Deciding if Sn1, Sn2, E1 or E2 will dominate
12. Synthesis I: Introduction to synthesis using halogenation of alkanes and substitution/elimination reactions
13. Biological methylating reagents

VIII. Alkenes

1. Nomenclature of alkenes
2. Review orbital illustration of alkene structure/bonding
3. Physical properties of alkenes
4. Review of cis-trans isomers in alkenes
5. Naming alkenes using the E,Z system
6. Relative stabilities of alkenes
7. Review mechanisms of pi electrons as a base
8. Mechanism of pi electrons as nucleophiles

IX. Reactions of Alkenes and Alkynes

1. Electrophilic addition reactions
2. Hydrogenation of an alkene
3. Addition of hydrogen halide to an alkene
4. Review of carbocation stability
5. Regioselectivity in electrophilic addition reactions (Markovnikov’s rule)
6. Hydration of an alkene (Markovnikov, Markovnikov without rearrangement, and anti-Markovnikov)
7. Addition of an alcohol to an alkene
8. Halogenation of an alkene
9. Halohydrin formation
10. Epoxidation of an alkene
11. Dihydroxylation of an alkene (anti and syn)
12. Ozonolysis of an alkane
13. Synthesis II: Synthesis using alkanes and alkenes
14. Introduction to alkynes
15. Acidity of terminal alkynes
16. Synthesis of complex alkynes using acetylide ions
17. N. Nomenclature of alkynes
18. Addition of a hydrogen halide to an alkyne (1 and 2 equivalents)
19. Hydration of an alkyne (Markovnikov and anti-Markovnikov)
20. Keto-enol tautomerization mechanism under acidic and basic conditions
21. Hydrogenation of alkynes
22. Ozonolysis of alkynes
23. R. Synthesis III: Multi-step synthesis with alkanes, alkenes, and alkynes
24. S. Synthetic polymers
25. Radicals in biological systems

X. Reactions of Alcohols, Amines, Ethers and Epoxides

1. Nomenclature of alcohols
2. Physical properties of alcohols
3. Substitution reactions of alcohols
4. Elimination reactions of alcohols
5. Oxidation of alcohols
6. Amines and their reactivity compared to alcohols
7. Nomenclature of amines
8. Nomenclature of ethers
9. Nucleophilic substitution reactions of ethers
10. Reactions of epoxides (ring opening under acidic and basic conditions)
11. Carcinogenicity of arene oxide
12. Synthesis VI: More multi-step synthesis including alcohols, ethers and epoxides

XI. Carbonyl Compounds I (Carboxylic Acids and Derivatives)

1. Nomenclature of carboxylic acids, acyl chlorides, esters and amides
2. Structure of carboxylic acids and their derivatives
3. Physical properties of carboxylic acids and their derivatives
4. Carboxylic acids and their derivatives found in nature
5. Nucleophilic acyl substitution reactions
6. F.Relative reactivities of carboxylic acids and their derivatives
7. Reactions of acyl chlorides with various nucleophiles
8. Reactions of esters including acid-catalyzed hydrolysis, transesterification and aminolysis
9. Ester hydrolysis under basic conditions and soaps, detergents and micelles
10. Reactions of carboxylic acids including Fisher esterification
11. Reactions of amides including acid-catalyzed hydrolysis
12. Synthesis of carboxylic acid derivatives
13. Nitriles and their reactions including hydrolysis and Sn2 reactions with the cyanide ion
14. Synthesis V: More multi-step synthesis including carboxylic acids and their derivatives

XII. Carbonyl Compounds II (Aldehydes and Ketones)

1. Nomenclature of aldehydes and ketones
2. Structure of aldehydes and ketones
3. Physical properties of aldehydes and ketones
4. Relative reactivity of aldehydes and ketones and their reactivity related to class I carbonyl compounds
5. Nucleophilic addition reactions
6. Grignard reagents and reactions with ketones, aldehydes, acyl chlorides and esters
7. Reduction of ketones and aldehydes with the hydride ion
8. Reduction of class I carbonyls with hydride ion
9. Reactions of aldehydes and ketones with amines (formation of imines and enamines)
10. Hydration of aldehydes and ketones
11. Hemiacetal and hemiketal formation
12. Acetal and Ketal formation
13. 1,2- and 1,4-addition to alpha, beta unsaturated carbonyl compounds
14. Biological conjugate addition reactions
15. Synthesis VI: More multi-step synthesis including aldehydes and ketones

XIII. Carbonyl Compounds III (Reactions at the alpha carbon) (Optional)

1. Alkylation of enolate ions
2. Aldol addition
3. Claisen condensation
4. Decarboxylation of ketoacids
5. Malonic ester synthesis
6. Acetoacetic ester synthesis

XIV. Aromaticity and Reactions of Benzene and Substituted Benzenes

1. Aromaticity and criteria for aromaticity
2. Aromatic heterocyclic compounds
3. Nomenclature of monosubstituted benzenes
4. Electrophilic aromatic substitution reaction mechanism
5. Halogenation, nitration and sulfonation of benzene
6. Friedel-Crafts acylation and alkylation of benzene
7. Reduction of carbonyl groups and nitro groups on benzene
8. Oxidation of alkyl groups on benzene
9. Nomenclature of disubstituted benzenes
10. Substituent effect on benzene reactivity
11. Directing effect of substituents on benzene
12. Synthesis VII: More multi-step synthesis including substituted benzenes

XV. Infrared Spectroscopy

1. Spectroscopy and the electromagnetic spectrum
2. IR spectroscopy
3. Fingerprint vs functional group region
4. IR stretching frequencies of importance
5. Effect of bond order
6. Effect of resonance
7. Intensity of absorption bands
8. Shape of absorption bands
9. Absence of absorption bands
10. Identifying IR spectra

XVI. Proton Nuclear Magnetic Resonance Spectroscopy (Optional)

1. NMR fundamentals including alpha and beta spin states, applied magnetic field and resonance
2. Shielding and effective magnetic field
3. Chemically equivalent protons and number of signals in a ¹H NMR spectrum
4. Chemical shift, integration and splitting patterns in a¹H NMR spectrum
5. Chemical shifts of various protons
6. Using a formula and a ¹H NMR spectrum to determine a structure

Laboratory Portion of Course

 I. Structure of Organic Compounds

1. Molecular modeling
2. Polarity and intermolecular forces

II. Solubility of Some Organic Compounds

1. Solubility
2. Solubility trends

III. Melting Point Determination

1. Theory
2. Melting point apparatus

IV. Recrystallization and Melting Points

1. Recrystallization process
2. Determining the best recrystallization solvent
3. Percent recovery
4. Recrystallization of benzoic acid
5. Recrystallization of an unknown
6. Melting point and mixed melting point to determine the identity of recrystallized unknown

V. Thin-Layer Chromatography (TLC)

1. Mobile and stationary phases in the development of a TLC plate
2. Visualizing chromatograms
3. Calculating R_f values
4. Identification of the components of a dye mixture using TLC
5. Analysis of Analgesics and Caffeine using TLC
6. Using TLC to monitor the synthesis of aspirin

VI. Chemically Active Extraction

1. Acid-base chemistry of carboxylic acids, amines and phenols
2. Separatory funnels and separations of mixtures of organic acids, bases and phenols
3. Development of a procedure
4. Rotary evaporator

VII. Dehydration of an Alcohol-An Elimination Reaction

1. Elimination review
2. Distillation
3. Infrared (IR) spectroscopy
4. Tests for unsaturation

VIII. Reduction of Methyl Oleate

1. Generation of hydrogen gas via reaction of zinc with sulfuric acid
2. Catalytic hydrogenation
3. IR spectroscopy of methyl oleate vs methyl stearate

IX. Competing Nucleophiles

1. Stationary and mobile phases in gas chromatography (GC)
2. Separation in gas chromatography
3. Nucleophilicities of chloride and bromide ions toward primary and tertiary substrates
4. GC analysis of substitution reactions with bromide and chloride ions

X. Chemiluminescence: Synthesis of Cyalume™

1. Theory
2. Synthesis of Cyalume™
3. Chemiluminescence with a fluorophore

XI. IR spectroscopy

1. IR of known compounds
2. Identification of unknowns using IR

XII. Grignard Reaction

1. Flame drying glassware
2. Synthesis of triphenylmethanol and IR analysis

XIII. Written Report on a chemist and their contribution to their field. The topic may be different, but should focus on organic chemistry and how it is involved in the world around the student.

Classroom discussion and problem solving: 10-35%

Laboratory: 20-25%
Mandatory Course Components:
None
Equivalent Courses:
None

1.   Essential judgment skills include the ability to identify, assess, and comprehend situations for the purpose of problem solving and coming to appropriate conclusions and/or course of actions.  Specifically, students must be able to:

• Apply mathematical concepts to solve problems
• Discern relevant and irrelevant information when solving problems
• Express knowledge of the appropriate level of chemistry in written and/or verbal formats
• Draw conclusions based on knowledge and experimental results
• Recognize unsafe situations in a laboratory environment

2.    Essential physical/neurological functions include the ability to use the senses of sight, hearing, touch, and smell. Students must meet  expectations necessary to safely perform tasks required to study chemistry, which include the need for manual dexterity and the ability to use sight and hearing. Specifically, students must be able to:

• Manipulate equipment and glassware to prepare for and conduct laboratory procedures
• Write in a laboratory notebook during the course of a laboratory experiment
• Observe and note changes (in color, sound, etc.) as experimental conditions progress or change
• Operate a computer for the purposes of inputting or graphing data and writing laboratory reports
• Operate analytical instrumentation for the purpose of collecting and analyzing data in the course of scientific study and experimentation
• Read and /or hear laboratory directions that involve either experimental procedures or safety concerns
• Inform the course instructor of any allergies (chemical, latex etc.) that may lead to an allergic reaction
• tolerate odors that are part of the chemistry lab environment

3.  Essential communication skills include the ability to communicate effectively with fellow students, faculty, and all members of the Physical Sciences department. Specifically, students must be able to:

• Understand written and verbal direction when completing tasks and assignments associated with the lecture portion of science courses
• Understand written and verbal directions when completing laboratory tasks and assignments
• Understand written and verbal directions when following all Departmental safety rules and procedures
• Communicate any issues that involve health or safety in a laboratory environment
• Use information technology skills consistent with effective communication.

4.  Essential emotional coping skills include the ability to demonstrate the mental health necessary to safely engage in the practice of scientific discovery.  Specifically, students must be able to:

• Engage in multitasking without becoming overly stressed
• Practice safe laboratory procedures and be mindful of the safety of others
• Realize that exposure to chemicals can have consequences if the correct safety procedures are not followed
• Collaborate with lab partners to complete a task in the classroom or laboratory
• Cooperate with others and work in groups or alone as indicated by the instructor

5.  Essential intellectual/conceptual skills include the ability to measure, calculate, analyze, synthesize, and evaluate to engage competently in the safe practice of Chemistry. Specifically, students must be able to:

• Select appropriate methods to solve mathematical problems
• Use a calculator to complete calculations
• Use a computer to generate graphs and reports
• Use equipment and instrumentation to make measurements
• Analyze complex graphical data and/ or concepts
• Express an understanding of the concepts learned in chemistry in written form or verbally

6.  Other essential behavioral attributes include the ability to engage in activities consistent with safe practice without demonstrated behaviors of addiction to, abuse of, or dependence on alcohol or other drugs that may impair behavior or judgment. The student must demonstrate responsibility and accountability for actions as a student in the Physical Sciences Department and as a developing professional in the field of chemistry consistent with accepted standards of practice.

Grand Rapids Community College strives to be more than ADA compliant. We strive to be accessible and welcoming to all students of all abilities. After reviewing the Essential Abilities/Technical Standards for this program; your responsibilities as a student entail determining if you can complete all associated coursework either:

• With Accommodation. I am otherwise qualified to meet the same academic standards as any other student entering the program. However, based on a medically documented condition or diagnosis, I would qualify for reasonable accommodation under the Americans with Disabilities Act (1990). I will meet with Disability Support Services on campus to arrange those accommodations in an interactive process with the department of Physical Sciences.
• Without Accommodation. I am able to complete the program without need for reasonable accommodation or modification. In the event my medical documentation reveals otherwise or a condition manifests that would necessitate an accommodation; it is my responsibility to inform a responsible authority figure within the department of (field of study) and work with Disability Support Services to see if a reasonable accommodation or modification can be made.