Organic Chemistry 201 Sections 4247

Organic Chemistry 201 Section 4275 Fall 2007

Instructor: Dr. Nadene Houser-Archield, Professor of Physical Sciences Office: Chesapeake Hall 310J Phone: 301 386 7593 E-Mail: [email protected] (note: the space between nhouser and archield is an underscore _) Include the code: CCGP07 in the subject (The code stops email messages from being evaluated as SPAM and does not allow emails that contain viruses or illegal attachments into our network.) Web page: http://academic.pgcc.edu/~nhousera/ Office hours (subject to change): M 11:00-11:50am, W 8:00-8:50am, T 4:00pm - 5:40pm Class Meeting Times: Lec Online Lab T 6:00pm - 09:30pm CH 320 Final Exam: Tuesday, December 11, 2007 6:00 - 9:30pm CH 320

DELAYED COLLEGE OPENINGS: When the College announces a delayed opening, all classes with at least 45 minutes of class time remaining at the time of the opening will be held. For example, in the event of a 10 a.m. opening, a 9:30-10:45 a.m. class will be held.

Course Materials: Textbook: Organic Chemistry, 2 nd Edition by Janice Gorzynski Smith Lab manual: Experiments and Activities will be provided on Blackboard Molecular Model kit: Not mandatory but strongly suggested. The University of Maryland, College Park bookstore sells several varieties. Safety Goggles (these are provided free of charge, in the lab) Blackboard notes, exercises and handouts: To log in to your Blackboard course, please follow these steps: Go to http://pgcconline.blackboard.com. NOTE: There is no "www" in the Blackboard address. If you do not have a myPGCC account: Go to http://my.pgcc.edu to receive a username and password Go to http://my.pgcc.edu to reset your myPGCC password Once you have a myPGCC account: Go to http://pgcconline.blackboard.com. type in your username and password You will see the Blackboard "Welcome" screen. In the box labeled "My Courses", click on the course name to enter your Blackboard course. Immediately change your Blackboard email address: 1. From YOUR Blackboard Welcome page click on Personal Information in the Tools Box on the left side. 2. Click on Edit Personal Information. 3. Change your email address to your preferred email address. 4. Click the Submit button in the lower right corner.

1 Welcome to Chemistry 201! This course is designed to immerse you in the basic tenets of organic chemistry. Laboratories, lectures, workshops and demonstrations will be the modes of information dispersal and skill acquisition. In order to be successful, read the chapters (prior to lecture is best), attend each lab, lecture and workshop, do the suggested homework problems and join/form a regularly meeting study group. You will need between 10 and 20 hours of study (outside of class time) per week!!! I am available during office hours. Also, the College Tutoring Center provides free tutoring services by appointment: 301 322 0748, Bladen Hall, room 107, Mon-Thurs.: 8:30 am – 8:30 pm, Fri.: 8:30 am – 4:30 pm, Sat.: 9 am – 3:30 pm www.pgcc.edu/students/tutoring_writing_grammar I strongly suggest forming study groups; those students who are strong in chemistry enhance their knowledge by teaching others; those who are weak in chemistry enhance their knowledge by being exposed to the way others view the course concepts.

Bring your calculator with you to lab. Visit the Physical Sciences and Engineering website at http://academic.pgcc.edu/psc Quizzes, exams, workshops, labs and the final exam will not be made up. Cheating on an assessment will result in a grade of zero for that assessment; the cheating will be reported to the office of records. CODE OF ACADEMIC INTEGRITY The college is an institution of higher learning that holds academic integrity as its highest principle. In the pursuit of knowledge, the college community expects that all students, faculty, and staff will share responsibility for adhering to the values of honesty and unquestionable integrity. To support a community committed to academic achievement and scholarship, the Code of Academic Integrity advances the principle of honest representation in the work that is produced by students seeking to engage fully in the learning process. The complete text of the Code of Academic Integrity is in the 2006-2007 Student Handbook (pages 44-47) and posted on the college's website.

CODE OF CONDUCT The Prince George's Community College Code of Conduct defines the rights and responsibilities of students and establishes a system of procedures for dealing with students charged with violations of the code and other rules and regulations of the college. A student enrolling in the college assumes an obligation to conduct himself/herself in a manner compatible with the college's function as an educational institution. Refer to the 2006-2007 Student Handbook, beginning on page 43, for a complete explanation of the Code of Conduct, including the Code of Academic Integrity and the procedure for dealing with disruptive student behavior.

Put your cell phone on vibrate or silent during class time. When an assessment of any sort is taking place turn off your cell phone. During an assessment (exam, quiz, lab practical) if you leave the classroom you may not return until the assessment is over.

DISABILITY SUPPORT SERVICES (use text provided below) Students requesting academic accommodations are required to contact the Disability Support Services Office (M- 1042) or call (301) 322-0838 (voice) or (301) 322-0122 (TTY) to establish eligibility for services and accommodations. Students with documented disabilities should discuss the matter privately with their instructors at the beginning of the semester and provide a copy of their Student/Faculty Accommodation Form.

2 Objectives for Chemistry 201

Upon completion of this course a student will be able to:

1) Categorize bonds according to polarity [ionic or covalent (polar covalent or nonpolar covalent, also coordinate covalent)], composition (sigma or pi), orbital character ( percentage s,p,d character), strength (% ionic character; % s,p,d character; single, double or triple; amount of overlap).

2) Apply principles of Valence Shell Electron Pair Repulsion theory to chemical formulas to determine Lewis dot structures, structural formulas, geometries and bond angles around central atoms, hybrid states of atoms, polarities of molecules and formal charges of atoms in molecules.

3) Employ structural formulas, classes, molar masses, polarities and/or types of interparticle forces and percentage hydrocarbon in compounds to predict states of matter, relative boiling and melting points, solubility properties, density, and flammability of compounds.

4) Employ resonance and/or inductive effects to determine electron richness or poorness of atoms.

5) Rank conformations according to stability/energy (steric hindrance, angle strain, bond strain, ring strain, eclipsing strain) using chair invertomers or Newman, sawhorse and Haworth projections.

6) Distinguish among structural isomers, stereoisomers [diastereomers (geometric and non-geometric), enantiomers (uses Fischer projections) and applies cis/trans, E/Z, R/S labels.

7) Name compounds and/or draws structural formulas for acyclic and cyclic hydrocarbons [alkanes, alkenes, and alkynes; substituted benzenes (benzoic acid, styrene, phenol, toluene, aniline, and 1,2- disubstituted benzenes], organic halides, nitro compounds, amines, alcohols, thiols, disulfides, ethers, aldehydes, ketones, carboxylic acids, anhydrides, esters, amides.

8) Employ qualitative analysis (litmus, Fehlings, Tollens, bisulfite, bicarbonate, KMnO4, K2Cr2O7, flame, 13 solubility, FeCl3, Br2, and TLC), instrumental analysis/spectroscopy (IR, mass spectroscopy, UV, C- NMR, 1H-NMR), elemental analysis, index of hydrogen deficiency to determine structures of molecules.

9) Rank organic acids, organic bases (and conjugate bases) according to strength

10) Analyze/evaluate/assess reactants, reaction conditions (solvent, temperature) to predict products for the following types of reactions: combustion, free radical substitution (optional), oxidation (of alkenes, alkynes, alcohols, aldehydes and thiols), reduction [of alkenes, alkynes (poisoned catalyst too), disulfides] and acid-base reactions (of carboxylic acids, carboxylate salts, amines and ammonium salts).

11) Analyze/evaluate/assess SN1, SN2, E1 and E2 reaction conditions (nucleophile/base, leaving group, solvent, steric hindrance, carbocation stability, base size) to predict products, reaction mechanisms, rearrangement, stereochemistry, regiochemistry, energetics (thermodynamic versus kinetic pathways and products), rate equations, molecularity and rate determining steps.

12) Analyze/evaluate/assess reaction conditions (carbocation stability, polarity of the addend, presence or absence of peroxides, temperature) to predict the products and regiochemistry of addition to alkenes and alkynes.

3 4 Grading Scale: A = 90-100% B = 80-89% C = 70-79% D = 60-69% F = 59% and below or insufficient labs or final exam not taken

Note 1: All labs are required! If you perform fewer than 90% of the labs you will receive a grade of F in the course. Note 2: If you do not take the final exam, you will receive a grade of F in the course. Note 3: Assignments are due during the first minute of class. Late assignments, if accepted, will be heavily penalized.

Assessment Percentage of grade Exams 40% Labs 25% Activities 10% Quizzes 05% Final Exam 20% Exams, quizzes, and labs will not be made up without official documentation such as emergency doctors’ notes, tow truck receipts timed and dated during the assessment period or funeral programs. If you are more than two minutes late for a quiz, you will not be allowed to take it or to make it up.

Tentative Course Schedule Week 1 Lab: 8/27 1) Molecular Structure Activity (no report due) 2) CHIME Internet Simulation Activity [Free Download (due at the beginning of the Week 5 lab)] Lecture: Review activities: Orbitals and Electron Configurations, The Periodic Table, Periodic Trends in Electronegativity. (Both the notes and the text reading are required) Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: 1.1, 1.2, 1.3

Week 2 Lab: 9/3 1) Begin Properties of Organic compounds and Melting points lab 2) ChemSketch Molecular Modeling Activity 2D and 3D [Free download (due at the beginning of the Week 4 lab)] Lecture: Review Activities: formula mass and molar mass calculations, the octet rule, balancing equations, intermolecular forces, and other review topics. (Both the notes and the text reading are required) Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: 3.3-3.7

5 Week 3 Lab: 9/10 1) Complete Properties Lab (due at the beginning of the Week 4 lab) 2) Begin 13 Unknowns Lab (Part 1, qualitative analysis) Lecture: Oxidation and Reduction, Quantitating Bond Polarity, Stoichiometry Review. Review reactions from 13 Unknowns lab. (Both the notes and the text reading are required) Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: 1.10, 1.11, 3.1, 3.2, 6.1, 13.4-13.7

Week 4 1) Properties of Organic Compounds lab and 9/17 2) ChemSketch Molecular Drawing 2D and 3D Activity are due at the beginning of today’s lab. Lab: 1) Exam 1 (1 hour; see course objectives on BlackBoard for topics) 2) More 13 Unknowns (Parts 1 and 2, qualitative analysis and infrared spectroscopy) Lecture: Valence Shell Electron Pair Repulsion (VSEPR) Theory. Review reactions from the 13 Unknowns lab. (Both the notes and the text reading are required) Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: 1.6, 1.12, 1.13, 6.1, 13.4-13.7

Week 5 CHIME Internet Simulation Activity is due at the beginning of today’s lab. 9/24 Lab: Complete 13 Unknowns (Parts 1 and 2, qualitative analysis and infrared spectroscopy): (due at the beginning of the Week 9 lab; it counts as 4 labs) Lecture: Hybridization and Organic Nomenclature. Review reactions from the 13 Unknowns lab. (Use the notes or the text reading) Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: 1.8, 1.9, 4.3, 4.4, 4.6, 7.2, 9.3A, 9.3B, 10.3, 11.2, 17.3, 19.2, 21.2, 22.3, 25.3

Week 6 Lab: 10/1 1) Barriers to Rotation Stereochemistry and Isomers Universal Model Kit activity (Part 1, no report due) 2) Newman projection Internet Simulation Activity (due at the beginning of the Week 7 lab) Lecture: 1H NMR and Elemental Analysis. Review reactions from the 13 Unknowns lab. Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: 4.9, 4.10, 10.2, 14.1-14.10,

Week 7 Newman projection Internet Simulation Activity due at the beginning of today’s 10/8 lab. Lab: Barriers to Rotation Stereochemistry and Isomers Universal Model Kit 6 activity (Part 2, no report due) Lecture: 13C NMR and Mass Spectroscopy. Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: 13.1-13.3, 14.11-14.12

Week 8 Lab: Exam 2 10/15 Lecture: Ultraviolet spectroscopy and a Model Spectroscopy exercise. Mid Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. term Text Reading, Chapters: 13.4, 16.15

Week 9 13 Unknowns lab is due at the beginning of today’s lab; counts as 4 labs. 10/22 Lab: Begin Organic Acids and Bases and Extraction Lecture: Resonance and Inductive Effects. Review Organic acids and bases and extraction lab and notes. Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: Chapter 2, 16.1-16.8

Week 10 No Lab: Professional Development Day 10/29 Lecture: Alkanes, Review Resonance and Acids and bases Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: Chapter 2, 4.7, 4.8, 4.11-4.14, 16.1-16.8

Week 11 Lab: 1) Complete Extraction Lab (Take weights, melting points, spectra) 11/5 (due at the beginning of the Week 12 lab) 2) Nucleophilic Substitution (a quick lab) (due at the beginning of the Week 13 lab) Lecture: Nucleophilic Substitution and Free Radical Substitution. Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: Chapter 7

7 Week 12 Extraction lab: due at the beginning of today’s lab 11/12 Lab: Begin Elimination (Reflux, Distillation, Gas Chromatography) Lecture: Elimination Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: Chapter 8

Week 13 Nucleophilic Substitution lab due at the beginning of today’s lab. 11/19 Lab: 1) Complete Elimination (Spectra and chromatography) (due at the beginning of the Week 15 lab) 2) Begin 3 Unknowns (TLC, multiple spectroscopies, multiple library media) Lecture: Addition Reactions Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: Chapter 10 Last Day to Drop is Tuesday, November 20, 2007

Week 14 Lab: Complete 3 Unknowns Lab (TLC, multiple spectroscopies, multiple library 11/26 media) (due at the end of today’s lab) Lecture: Reactions of Alcohols (Much of this will be review) Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard. Text Reading, Chapters: Chapter 9

Week 15 Elimination lab: due at the beginning of today’s lab. 12/3 Lab: 1) Exam 3 Lecture: Review

Week 16 Tuesday, December 11, 2007, 6:00 -9:30pm CH 320 12/10 Final Exam (Cumulative all topics, 40% synthesis) Have a Wonderful Holiday!

8 Relevant Academic Programs

STEM Collegian Center http://academic.pgcc.edu/collegiancenters The College’s STEM Collegian Center provides a “place to belong” for STEM majors. It brings STEM students together for co-curricular activities and opportunities:

STEM – science, technology, engineering and mathematics 301-341-3086

Honors Academy/Program 301-322-0433 Marlboro Hall, Room 1087 The Honors Academy admits academically outstanding honors students who are interested in a rigorous program of academic excellence, intellectual development, leadership and community service. Prince George's Community College Honors Program promotes students’ intellectual growth and enrichment.

International Education Center 301-322-0177 Lanham Hall, Room 117 http://academic.pgcc.edu/internationalcenter The International Education Center provides academic support and assistance to students who need help with courses or with understanding the American higher education system. The Center brings international and American students together for learning enrichment activities, including a variety of discussion forums that foster awareness and understanding of cultural issues.

CAMPUS RESOURCES AND SERVICES:

Student Development Services Student Development Services offers programs that provide students with advising, individual counseling, and mentoring. For more information, call 301-322-0886 or check the website: www.pgcc.edu/pgweb/pgdocs/student_services/index-sds.htm.

Computer and Learning Labs Office Location Phone Hours of Operation

Learning Lab Marlboro Hall 301-322-0503 Mon.-Thurs.: 8 am – 9 pm Room 2129 Fri.: 8 am – 4 pm Sat.: 8:30 am – 3 pm Sun.: 10 am – 1 pm Open Computer Lab Bladen Hall 301-322-0999 Mon.-Thurs.: 8 am – 10 pm Room 104 Fri.: 8 am – 5 pm Sat.: 9 am – 5 pm Sun.: Closed

Other Resources, Services, and Academic Support 9 Office Location Phone Hours of Operation

Bookstore Largo Student 301-322-0912 Hours vary at beginning and end of Ctr. Room 116 the semester. Please call or check website to confirm. www.pgcc.edu/pgweb/pgdocs/bookstore.html

College Life Services Largo Student 301-322-0853 Mon.-Fri.: 8:30 am – 5 pm Ctr. Room 149

Distance Learning Accokeek Hall 301-322-0463 Mon.-Thurs.: 8:30 am to 8 pm www.pgcconline.com Room 313 Fri.: 8:30 am to 6 pm Phone support available M-F: 8:30 am to 9 pm

Library Accokeek Hall 301-322-0105 Mon-Thurs.: 8 am – 8 pm www.pgcc.edu/library Fri.: 8 am – 5 pm Sat.: 10 am – 3 pm Sun.: Closed

Tutoring and Writing Bladen Hall 301-322-0748 Mon-Thurs.: 8:30 am – 8:30 pm Centers Room 107 Fri.: 8:30 am – 4:30 pm Sat.: 9 am – 3:30 pm www.pgcc.edu/students/tutoring_writing_grammar

Important Dates September Saturday- Labor Day. COLLEGE CLOSED 1-3 Monday September Friday Last day to change from “credit” to “audit” status or vice versa. 28 October 17 Wednesday Mid-Term October 30 Tuesday Professional Development Day- No Classes November Tuesday Last day to withdraw 20 November Wednesday Thanksgiving break begins—College closed 21 Dec 10 Monday Last day of regular classes for the Fall semester Dec 11 Tuesday Final examination 6:00 - 9:30pm CH 320