Organic Chemistry I - Cm2113 Fall 2003

ORGANIC CHEMISTRY I - CM2113 FALL 2003

INSTRUCTOR: J. Ronald Boone OFFICE: MS412 TELEPHONE: 279-5710 E-Mail: Boonejr or [email protected] OFFICE HOURS: M 1:00-4:00 (Office hours T 1:30-3:30(office/library) will be posted W 8:00-9:00; 1:00-2:00 on the door.) R 9:30-11:30(office/library) F 8:00-9:00: Other times by appointment. [I am in class MWF @:00; T @ 5:30-10:00; W @ 2:00-6:00(lab); R @ 2:45-6:45(lab)]

TEXT: ORGANIC CHEMISTRY by L. G. Wade (6th ed.; Prentice Hall)

The goal of the course is to have the student acquire a basic knowledge of organic chemistry beginning with bonding and molecular structure. This will be supplemented and emphasized using nomenclature of functional groups and organic compounds. Basic principles of organic reactions will be introduced by studying such reactions as hydration, dehydration, SN1, SN2, E1, E2, and others. The mechanisms of some of the above reactions will be examined in order to point out fundamental mechanistic principles for future applications. Organic syntheses will be introduced along with the concepts of how to plan the synthesis of a target molecule. Infrared spectroscopy and mass spectrometry will briefly be introduced in lecture then followed up in more detail in the laboratory. The laboratory course(CM2211) is a co-requisite for the lecture course. Infrared spectroscopy and the mass spectrometry are certainly laboratory subjects and will be primarily taught in the laboratory but will be utilized in this lecture course because of their usefulness confirm and demonstrate theory, structure, and reaction mechanisms. IR and MS are major topics in the lecture book and the laboratory serves to give the student first-hand experiences for understanding them. A copy of a study guide / solutions manual should be available the bookstore.

Introduction, Lewis Structures, Resonance, Acids and Bases (chap. 1) Structure, Molecular Orbitals, Hybridization, Functional Groups, Isomers (chap. 2) Infrared Spectroscopy [primarily from lab](chap. 12) Structure, Nomenclature, Conformations, and Stereochemisty (chap. 3) Reactions, Free Radical Halogenation, Mechanisms, Kinetics (chap. 4) Stereochemistry (chap. 5) Alkyl Halides, Nucleophilic Substitution and Elimination Reactions (chap. 6) Alkenes and more Elimination Reactions (chap. 7) Addition Reactions of Alkenes(chap. 8) Alkynes (chap. 9) Alcohols (chap. 10) Reaction of Alcohols (chap. 11) Infrared Spectroscopy and Mass spectrometry [primarily from lab](chap. 12) Ethers (chap. 14) GRADING Scale A 90 - 100 FIVE TESTS @ 100 500 B 80 - 89 C 70 - 79 Other quizzes and homework(approx?) 100 D 60 - 59 FINAL (comprehensive)@ 200 200 F < 50 TOTAL (approx) 800

AVERAGE = POINTS EARNED / TOTAL POSSIBLE POINTS

(The fifth test and the Final will be taken at the Final Exam period)

ATTENDANCE

Attendance is expected. Send an explanation for any absence or tardy is to be reported by E-mail. This will enable the instructor to have a written record. The E-mail address is BOONEJR or [email protected]; the subject of the e-mail should be Organic Absence or Tardy (date). Tardies may result in points off. Class attendance is required according to the University’s Catalog.

Tests or work missed due to unexcused and unjustifiable absences cannot be made up.

Tests or work missed due to excused absences may be made up for full credit. These usually are sickness (with doctor excuse) or death in immediate family.

Tests or work missed due to unexcused but justifiable absences may be made up but for less than full credit. These usually are planned absences and the instructor is informed beforehand.

The instructor will have to decide how a missed test or work is to be made up.

Tardiness is a form of absenteeism and it will be treated as such.

Absences from daily quizzes or work cannot be made up since to some degree they measure attendance and class participation.

In laboratory courses or courses with a laboratory, failure to do two or more laboratory exercises will result in a final grade of F for the course regardless of the overall course average.

A student’s final average cannot be higher than his percent attendance.

HOMEWORK, ASSIGNMENTS, AND READINGS

All problems at the end of the covered chapters are assigned. A problem notebook should be maintained and kept up to date. Notebooks are subject to being checked at any time. (Obviously problems related to "skipped" material may also be skipped.) Homework assignment may be given by E-mail. Reading assignments from current journals and books may be given. Important information, reaction, and mechanism cards should be prepared on a regular basis (4" x 6", reactants on front, products on back)

The class will be conducted according to Lipscomb’s Academic Honor Code and students will be requested to sign the pledge: “On my honor as a gentleman/lady, I have neither given nor received unauthorized aid on this examination/assignment and if I have observed such actions, I will follow the prescribed honor code procedures.” Collaboration and discussion of homework problems are common practices and are okay for the most part (The instructor will make clear when no collaborations should take place). Collaboration is not the blatantly copying the work of another. During a test or quiz you may not simply exit the room to go to the rest room. You should request permission and turn in your test, and when you return you may resume the test in a front row seat. No electronic devices, cell phones, pagers, calculators (except those that are approved) are to be used or present during a test or quiz.

RECOMMENDATIONS FOR STUDYING

Read the chapter.

Work the problems within the chapter as you go.

Think visually -- Draw it -- Use models.

Do the pre-lecture quiz on the chapter.

Work the problems at the end of the chapter.

Re-read the chapter and try again on the problems you were unable to work the first time.

Listen.

Take notes. Copy and fill in your notes, everyday. Make reaction cards.

Ask questions.

Study regularly – daily, nightly, and weekends.

The chapter summaries outline what you should know and be able to do.

Tests are closed book. Can you work the problems without using the text book and answer book? The answer book always makes it look easy, maybe too easy.

Pre-lecture chapter quizzes on WebCT (Lipscomb Central under secure aea or better just use Webct.Lipscomb.edu) In order to encourage the student to read the chapter, a pre-lecture quiz will be given on each chapter. The student is to read the chapter, then answer a few (3-6) short answer questions on the chapter using WebCT. There will be a time limit on each quiz (15-30 minutes). In general, a quiz will be due at midnight following the first lecture on a chapter. (e.g. If the first lecture on a chapter is on Wednesday, the quiz for that chapter must be completed by midnight of Wed/Thurs.)

Many of the questions will be multiple choice. A question that is short answer must be specifically and exactly answered in order for the computer to accept it. Therefore I plan to give questions requiring answers such as names, numbers, molecular formulas, yes, no, ect.

For entering “short answer” answers “the rules are”:

For numerical answers use the numbers: 1 (not one) 4 (not four)

For words and chemical names use lower case only: yes (not Yes) methane (not Methane)

For chemical symbols will use upper and lower cases just as on the periodic chart: Cu

For chemical/molecular formulas use the following guidelines: organic formulas are to be written C first, H second, followed by O, then the other elements alphabetically. Numeric subscripts are not be used to enter answers, just enter regular numbers: C5H10OClN = C5H10OClN (watch the zeroes and the letter O’s) C, H, O (others in alphabetical order following O)

For small inorganic formulas use their most common forms: HCl as HCl (not ClH), H2O as H2O (not OH2), CaCl2 as CaCl2 (not Cl2Ca), etc.

If a question requires several short answers, they are to be separated with a semi-colon followed by a space : ans; ans; ans; ans: ….. (e.g. …..is the first structure in each pair…? Then give the answer for each pair as: no; yes; no; no)

If the question requires selecting an answer from a list, the list will use Roman numerals (or letters), so use the Roman numerals (or letters) to answer the questions: (e.g. …. Which is the smallest ion? The largest? I. I - II. Br - III. Cl - IV. F - Then give the answer as: IV; I [Note: Roman numerals are upper case]

Remember to submit the answer to each question at each question.