CODE CHEM 204 TITLE: Organic Chemistry II INSTITUTE: STEM DEPARTMENT: Chemistry COURSE DESCRIPTION: A continuation of CHEM-203, students will extend their studies into topics including aromatic hydrocarbons, amines, carboxylic acids, aldehydes, ketones and carbanion chemistry. PREREQUISITES: A grade of C or higher in CHEM203 PREREQUISITES OR COREQUISITES: COREQUISITES: CREDITS: 5 LECTURE HOURS: 4 LAB/STUDIO HOURS: 3 REQUIRED MATERIALS: TEXT AND LABORATORY MANUAL: SEE https://www.brookdalecc.edu/college-store/textbooks/ SAFETY GOGGLES: NEW JERSEY STATE LAW REQUIRES THAT ALL STUDENTS WEAR APPROPRIATE SPLASH AND IMPACT PROOF SAFETY GOGGLES WHILE PERFORMING LABORATORY EXPERIMENTS, OR DURING DEMONSTRATION OF EXPERIMENTS. THEY ARE AVAILABLE AT THE COLLEGE STORE. Optional Materials: COURSE LEARNING OUTCOMES: UPON COMPLETION OF THIS COURSE, THE STUDENT WILL BE ABLE TO: Utilize the scientific critical thinking, informational & technical literacy and mathematical skills learned in General Chemistry and Organic Chemistry I to understand concepts and problem solve in more advanced topics in organic chemistry. Name, draw, predict results, interpret spectra for, synthesize and explain reaction mechanisms for aromatic hydrocarbons, amines, carboxylic acids and their derivatives, aldehydes, ketones and carbanion chemistry. Prepare, isolate and identify organic compounds using laboratory instrument techniques. GRADING STANDARD: Upon completion of the course, grades will be assigned as follows: A = 92 100% A- = 89-91% B+ = 86-88% B = 82-85% B- = 79-81% C+ = 76-78% C = 70-75% D = 65-69% F = <65%
Unit examination results will be reported as the grade assigned by the faculty calculated to the first decimal place. These grades will be weighed according to course grading policy. In calculating the course grade, 0.5 will round up to the next numerical grade and 0.4 will round down to the next lower numerical grade. 1. The total laboratory grade will be based on an average of fourteen (14) laboratory experiments and an average of six (6) laboratory quizzes given through the semester. The experiment average will make up 80% of the final grade and the quiz average will make up 20% of the final grade. 2. Any missed lab will be averaged in as a zero (0). Students will have the opportunity to make up one (1) missed laboratory experiment during the semester with a valid excuse. There will be time scheduled by the learning assistant in charge of the lab for this purpose. 3. Any missed laboratory quiz will not be made up. COURSE CONTENT: UNIT 1 Alkynes, Dienes, and Aromatic Compounds UNIT 2 Aldehydes, Ketones and Spectroscopy UNIT 3 Carbanion Chemistry, Carboxylic Acids and Acid Derivatives UNIT 4 Amines and Heterocycles DEPARTMENT POLICIES Chemistry Laboratory Policies 1. Students must attend their scheduled laboratory section. Students are not allowed to attend any other lab section for any reason. 2. Students must pass both the lecture and the laboratory portion of the course. COLLEGE POLICIES: For information regarding: Brookdale s Academic Integrity Code Student Conduct Code Student Grade Appeal Process Please refer to the STUDENT HANDBOOK AND BCC CATALOG. NOTIFICATION FOR STUDENTS WITH DISABILITIES: Brookdale Community College offers reasonable accommodations and/or services to persons with disabilities. Students with disabilities who wish to self-identify, must contact the Disabilities Services Office at 732-224-2730 or 732-842-4211 (TTY), provide appropriate documentation of the disability, and request specific accommodations or services. If a student qualifies, reasonable accommodations and/or services, which are appropriate for the college level and are recommended in the documentation, can be approved. ADDITIONAL SUPPORT/LABS: Learning assistants are available for help for both lab and lecture. The times of availability are posted at the learning assistants office. For any additional information, please call the Chemistry Department at 732-224-2424. WEBSITE: https://www.brookdalecc.edu/stem-institute/chemistry/ 2
CHEM-204 Unit 1 Unit 1 of 4 Units Course Objectives: Students will be able to name, draw, give properties, predict reaction products and provide mechanisms for selected reactions for the major classes of organic compounds. The laboratory will include preparation, isolation reaction and identification of organic compounds using modern instrumental techniques. Name of Unit: Alkynes, Dienes, and Aromatic Compounds. Unit Objective: Students will be able to explain: (1) keto-enol tautomerism, (2) the acidity of terminal alkynes and phenols, (3) addition reactions to conjugated dienes, (4) resonance and aromaticity, (5) give physical properties for, synthesis and predict products for Electrophilic Substitution reactions for Benzene and its derivatives and (6) predict the effect of any given group on the acidity of phenols and benzoic acids. Text: Loudon, G. Marc, Organic Chemistry, 4th edition: Chapters 14( 4-7), 15( 1,4,6,7), 16, 17 ( 1-2,5) and 18 ( 6). Lab Manual: Landgrebe,, John A, Theory and Practice in the Organic Laboratory, 5 th edition, Brooks/Cole Publishing Company, 2004. Experiments: 26 (Kinetic and Thermodynamic Reaction Conditions), 27 (Measurement of Resonance Energy), 32 (Friedl-Krafts Alkylation) Objectives You will be able to: 1. name and draw: a. alkynes b. dienes and c. aromatic compounds. 2. for Alkynes provide products and mechanisms for: a. Addition reactions b. Hydration and c. Hydroboration-Oxidation d. Hydrogenation (including stereochemistry) 3. explain the acidity of terminal (1-) alkynes And the basicity of their conjugate bases 4. for conjugated dienes provide products and mechanisms for addition reactions. Recommended Learning Experiences 1. Chapter 14 Problems: 14.1-2 Chapter 16 problems: 16.1-2, 16.34 2. Chapter 14 Problems: 14.8-15, 14.26 3. Chapter 14 Problems: 14.16-23 4. Chapter 15 Problems: 15.20-23, 15.35 (a-d), 15.50, 15.53. 3
CHEM-204 Unit 1 Unit 1 of 4 Units 5. draw and evaluate relative stabilities of resonance structures. 6. describe characteristics that make a species (molecule, cation, anion or free radical) aromatic and recognize species as being aromatic. 7. describe the physical properties of aromatic compounds and explain variations in physical properties especially with respect to boiling, melting, solubility and density. 8. for benzene and its derivatives provide products and mechanisms for electrophilic aromatic substitution reactions. Also predict products for side chain oxidation. 9. using resonance as part of your explanation explain the activating and directing properties of any given substituent on a benzene ring. 10. using resonance as part of your explanation explain allylic and benzylic reactivity and show mechanisms for their reactions. 11. using resonance as part of your explanation explain the influence of any given substituent on the acidity of phenols and carboxylic acids. 12. Experiments: a. 26 (Kinetic and Thermodynamic Reaction Conditions), b. 27 (Measurement of Resonance Energy), c. (Friedl-Krafts Alkylation) 5. Chapter 15 Problems: 15.26-31, 15.34, 6. Chapter 15 Problems: 15.39-40 7. Chapter14 Problems: 14.6-7, 14.37, 14.41-42 Chapter15 Problems: 15.9-11 Chapter16 Problems: 16.3, 16.5-9, 16.35, 16.50-51 8. Chapter 16 Problems: 16.12-21, 16.24, Chapter 17 Problems: 17.10-11 9. Chapter 16 Problems: 16.22-23, 16.25-26, 16.40-44 10. Chapter 17 Problems: 17.1-5, 17.15-16, 17.17 (a,b), 17.23-25. 11. Chapter 18 Problems: 18.8-10, 18.20-22, 18.24, 18.30 12. Experiments a. Diene addition reaction b. Ketone Preparation c. Electrophilic Aromatic Substitution reaction 4
CHEM-204 Unit 2 Unit 2 of 4 Units Course Objectives: The student will be able to name, draw, give properties, predict reaction products and provide mechanisms for selected reactions for the major classes of organic compounds. The laboratory will include preparation, isolation reaction and identification of organic compounds using modern instrumental techniques. Name of Unit: Aldehydes, Ketones and Spectroscopy. Unit Objective: Students will be able to identify compounds from their molecular formulae, Infra-Red and NMR spectra. Students will also be able to name, give physical properties for, synthesize and predict products for addition reactions for aldehydes and ketones. Text: Loudon, G. Marc, Organic Chemistry, 4th edition: Chapters 12 (omit 6), 13, 19. Lab Manual: Landgrebe, John A, Theory and Practice in the Organic Laboratory, 5 th edition, Brooks/Cole Publishing Company, 2004. Experiments: 24 [Omit C] (Oxidation of (-)-Borneol to (-)-Camphor), 30 (IR), 31 (NMR) 19 (Divalent Carbon Intermediates; Phase-Transfer catalysis). Objectives You will be able to: 1. Perform calculations involving wavelength, wavenumber, frequency and energy. 2. Correlate IR position of absorption with bond strength. 3. Determine degrees of unsaturation from a molecular formula. 4. Use Infrared and/or NMR spectra to identify compounds. 5. For NMR spectra use or predict: a. degree of unsaturation ( ) b. number of peaks c. chemical shifts ( ) d. peak areas and e. splitting to interpret NMR spectra. Recommended Learning Experiences 1. Ch 12 Problems: 12.1-12.4, 12.6 2. Ch 12 Problems: 12.5-12.26 3. Read Ch 4: 4.3 Ch 4 problems: 4.7-4.10 4. Ch 12 Problems: 12.8-10, 12.23, 12.28 Ch 13 Problems: 13.13, 13.14, 13.31, 13.37, 13.39, 13.44, 13.47 Ch 19 Problems:19.4-7, 19.63, 19.65-66 5. Ch 13 Problems: 13.1-13.8, 13.10, 13.19, 13.20, 13.24, 5
CHEM-204 Unit 2 Unit 2 of 4 Units 6. correlate electronegativity, proximity to electronegative groups, contributions of multiple groups, class (1 o, 2 o, 3 o ), hybridization, hyperconjugation and unsaturation with chemical shifts in NMR. 7. name and draw Aldehydes and Ketones. 8. describe the physical properties of Aldehydes and Ketones and explain variations in physical properties especially with respect to boiling, melting, solubility and density. 9. for Aldehydes and Ketones to synthesize them and provide products and mechanisms for Nucleophilic Addition, oxidation reactions and reactions with acids. 10. demonstrate laboratory techniques in: a. 24 [Omit C] (Oxidation of (-)-Borneol to (-)-Camphor), b. 30 (Infra-Red Spectroscopy), c. 31 (NMR Spectroscopy), d. 19 (Divalent Carbon Intermediates). 6. Ch 13 Problems: 13.4 7. Chapter 19 Problems: 19.1-2 8. Chapter 19 Problems: 19. 9. Chapter 19 Problems: 19.12-14, 19.18-24, 19.27-33, 19.37, 19.38-39, 19.49, 19.54 10. Experiments a. Ketone Preparation b. Spectral Compound Identification c. Spectral Compound Identification d. Phase-Transfer Catalysis 6
CHEM-204 Unit 3 Unit 3 of 4 Units Course Objectives: The student will be able to name, draw, give properties, predict reaction products and provide mechanisms for selected reactions for the major classes of organic compounds. The laboratory will include preparation, isolation reaction and identification of organic compounds using modern instrumental techniques. Name of Unit: Carbanion Chemistry, Carboxylic Acids and Acid Derivatives. Unit Objective: Students will be able (1) explain carbanion stabilities, (2) explain the acidity of carbonyl compounds, (3) for Aldol and Claisen Ester Condensations predict products and give mechanisms and (4) for Carboxylic Acids and their derivatives name, draw, explain physical properties, synthesize them and predict reaction products. Text: Loudon, G. Marc, Organic Chemistry, 4th edition: Chapters 20, 21 and 22 (1-4, 5A, 10). Lab Manual: Landgrebe, John A, Theory and Practice in the Organic Laboratory, 5 th edition, Brooks/Cole Publishing Company, 2004. Experiments: 46 (9-Benzal & 9-Benzofluorene Aldol Condensation and Cannizzarotype Reactions), 21 (Triphenylcarbinol; Addition of a Grignard reagent to a Ketone), 47 (Electronic Effects of Substituents in Reactions; Acidity Constant Determination). Objectives You will be able to: 1. name and draw any given Carboxylic Acid, Ester, Amide, Acid Chloride or Acid Anhydride. 2. provide products and mechanisms for: a. the Haloform reaction b. Aldol and Claisen Ester Condensations (regular and Crossed), c. Organometallic Additions 3. Explain the acidity of carbonyls using resonance structures as part of your explanation.. 4. describe the physical properties of Carboxylic Acids, Esters, Amides, Acid Chlorides and Acid Anhydrides and explain variations in physical properties especially with respect to boiling, melting, solubility and density. Recommended Learning Experiences 1. Chapter 20 Problems: 20.1-2 Chapter 21 Problems: 20.1-4 2. Chapter 22 Problems: 22.13-14, 22.18-24, 22.26-27, 22.42-43, 22.47, 22.49,- 50, 22.52, 22.57, 22.71(a-d), 22.72(a,c,f) 3. Chapter 22 Problems: 22.1-9, 22.13-14, 22.49-50, 22.52-53, 22.61 4. Chapter 20 Problems: 20.3-6, 20.53, 20.55-56 Chapter 21 Problems: 21.5-8, 21.48, 21.55 7
CHEM-204 Unit 3 Unit 3 of 4 Units 5. for Carboxylic Acids and their derivatives synthesize them and provide products and mechanisms for their reactions. 6. using resonance and polar (inductive) effects explain acidity trends for Carboxylic Acids. 7. Experiments: a. 46 (9-Benzal & 9-Benzofluorene Aldol Condensation and Cannizzaro-type Reactions), b. 21 (Triphenylcarbinol; Addition of a Grignard reagent to a Ketone), c. 47 (Electronic Effects of Substituents in Reactions; Acidity Constant Determination). 5. Chapter 20 Problems: 20.7-21, 20.25-30, 20.36, 20.45-46 Chapter 21 Problems: 21.10-29, 21.33-34, 21.40, 21.42, 21.46, 21.48, 21.51, 21.54 6. Chapter 20 Problems: 20.7-8, 20.30-31, 20.35 Chapter 21 Problems:21.9 7. Experiments: a. Aldol Condensation and Cannizzaro Reactions b. Grignard reagent c. Substituent Effects on Benzoic Acid derivatives pk a s. 8
CHEM-204 Unit 4 Unit 4 of 4 Units Course Objectives: The student will be able to name, draw, give properties, predict reaction products and provide mechanisms for selected reactions for the major classes of organic compounds. The laboratory will include preparation, isolation reaction and identification of organic compounds using modern instrumental techniques. Name of Unit: Amines and Heterocycles. Unit Objective: Students will be able explain (1) amide-iminol tautomerism, (2) the basicity of amines, (3) aromaticity of heterocycles. Students will also be able to name, draw, explain physical properties for, synthesize and predict reaction products for Amines and Heterocycles. Text: Loudon, G. Marc, Organic Chemistry, 4th edition: Chapters 23, 24( 2-3, 6). Lab Manual: Landgrebe, John A, Theory and Practice in the Organic Laboratory, 5 th edition, Brooks/Cole Publishing Company, 2004. Experiments: 41 (Fischer Esterification), 48 Synthetic Dyes and 50 (Qualitative Organic Analysis; Classification Tests). Objectives You will be able to: 1. name and draw and subclassify (1 o, 2 o, 3 o, 4 o ) any given Amine and Heterocycle. 2. Explain the basicity of Amines. And the acidity of their conjugate acids. 3. for Amines and Heterocycles synthesize them and provide products and mechanisms for electrophilic aromatic substitution reactions. Also predict products for side chain oxidation. 4. using resonance as part of your explanation explain the aromatiity of the aromatic heterocycles. 5. describe the physical properties of Amines and explain variations in physical properties especially with respect to boiling, melting, solubility and density. Recommended Learning Experiences 1. Chapter 23 Problems: 23.1-2, 23.12-13 Chapter 24 Problems: 24.5-6 2. Chapter 23 Problems: 23.8-9, 23.37 Chapter 24 Problems: 24.10-11, 24.39 3. Chapter 23 Problems: 23.14-30, 23.34-36, 23.38-39, 23.48, 23.58, 23.60-61, 23.72 Chapter 24 Problems: 24. 4. Chapter 24 Problems: 24.7, 24.12, 24.36 5. Chapter 23 Problems: 23.3-7, 23.10-11, 23.64-66 Chapter 23 Problems: 24.8-9 9
CHEM-204 Unit 4 Unit 4 of 4 Units Objectives Recommended Learning Experiences 6. Experiments: a. 41 (Fischer Esterification), b. 48 Synthetic Dyes and c. 50 (Qualitative Organic Analysis; Classification Tests). 6. Experiments a. Esterification b. Diazonium Dyes c. Chemical Tests for Classes of Organic Compounds. 10