ORGANIC CHEMISTRY Fall, 2005 TTh 8-12 Michael B. Smith Chemistry A-416 (860) MWF 1-3 PM, TTh 12-2 PM; any other time by appointment

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1 ORGANIC CHEMISTRY Fall, 2005 TTh 8-12 Michael B. Smith Chemistry A-416 (860) Office Hours: MWF 1-3 PM, TTh 12-2 PM; any other time by appointment SYLLABUS EXAMS There will be 1 exam given in class on Thursday, October 6 (the mid-term exam). This exam is worth 100 points. The final exam date will be set by the University. The final exam is worth 100 pints. NO MAKE UP EXAMS WILL BE GIVEN EXCEPT IN THE CASE OF A DOCTOR'S EXCUSE. IF THERE IS ANOTHER IMPORTANT CONFLICT WITH THE EXAM TIME, MAKE UP EXAMS MAY BE GIVEN BUT YOU MUST SEE ME AT LEAST ONE WEEK IN ADVANCE. The only conflicts which are acceptable are scheduled University functions such as another course, lecture or laboratory, participation (not attendance) in concerts, practices, etc. QUIZZES. Eight (8) 15 minute quiz will be given during the lecture portion of the class on September 1, September 8, September 20, September 29, October 13. November 3, November 15, and December 6. Each quiz will cover lecture and lab material. Each quiz is worth 30 points and the lowest two grades will be dropped. REQUIRED TEXTBOOK: Kenneth Williamson s Macroscale and Microscale Organic Experiments, Fourth Edition (Houghton Mifflin Company). You are required to purchase a laboratory notebook, and all experiments will be recorded in that notebook. The notebook will be collected and inspected at the discretion of the instructor and/or the teaching Assistant in charge of your section. SAFETY GOGGLES ARE REQUIRED AT ALL TIMES. Glasses or glasses with side shields are not an appropriate substitute in this lab. It is strongly recommended that you not wear contact lenses in the lab because they present a hazard if anything does get in your eyes. YOU MAY NOT WEAR SANDALS, CLOGS OR OTHER FOOTWEAR THAT INADEQUATELY PROTECTS THE FEET. YOU MUST WEAR SOCKS AS WELL AS SHOES. It is also highly recommended that you wear long pants or a lab coat in the lab. 1

2 BASIS FOR YOUR GRADE Lab Notebook: 200 points. The entire notebook will not be graded. Experiments for grading will be selected at random. Therefore notes for all experiments should be done carefully. This grade will be based primarily on the section in your notebook that describes what you actually did or observed in the laboratory. Part of the grades for products will also be based on your discussion of results in the notebook. That grade is in addition to the 200 points discussed here. See below. Quizzes: 240 points (30 each). Eight quizzes will be given and the two lowest grades will be dropped. Therefore, Quizzes will be counted for 180 points. Midterm and Final Exam: 200 points (100 for midterm and 100 for final). Unknowns: 85 points 15 for mp 20 each for TLC and fractional distillation 30 for aldehyde-ketone). Quality of products and discussion of results: 340 points: 10 points each for recrystallization and fractional distillation 20 points for steam distillation; 30 points each for 1-bromobutane, cyclohexanone, aldol, Diels-Alder, acetylsalicylic acid, nitration, Grignard, Wittig, and polymer 50 points multi-step sequence. Discretionary points: 135 points (given by the instructor and TA on the basis of attributes such as: understanding what you are doing and why you are doing it, curiosity, ability to apply reasoning and logic to unusual observations, ability to solve problems as they arise, tenacity, perseverance, integrity, etc.) Students not showing up for clean-up and checkout will lose 300 points. The total number of points in this course is

3 MUST HAVE SAFETY GOGGLES TO START ANY EXPERIMENT YOU WILL NOT BE ALLOWED IN THE LAB WITHOUT SAFETY GOGGLES YOU WILL NOT BE ALLOWED IN THE LAB WEARING SANDALS FAILURE TO DISPOSE OF CHEMICALS PROPERLY, OR TO OBEY INSTRUCTIONS BY THE TA WILL RESULT IN YOUR DISMISSAL FROM THE LABORATORY Date Lab and Lecture Assignments Readings Tues Aug 30 Tues Aug 30 Lecture 1: Introduction and Safety Check-in Thurs Sept 1 Lecture 2; Quiz 1 (safety) Thurs Sept 1 Melting point exp. pages 25-37; (page 70), 4-3 (page 71), 4-4 (page 71) Identify an unknown Tues Sept 6 Lecture 3 Tues Sept 6 Recrystallization pages (page 56), 3-3 (page 59), 3-5 (page 60) Thurs Sept 8 Lecture 4; Quiz 2 Thurs Sept 8 Extraction pages (pages ) Tues Sept 13 Tues Sept 13 Finish Extraction Thurs Sept 15 Lecture 5 Thurs Sept 15 Thin-Layer Chromatography pages (page 160), TLC unknown (handout) Tues Sept 20 Lecture 6; Quiz 3 Tues Sept 20 Steam Distillation pages (pages ) Thurs Sept 22 Thurs Sept 22 Finish Steam Distillation pages

4 Tues Sept 27 Lecture 7 Tues Sept 27 Simple/Fractional Distillation pages Fractionally Distill Unknown Identify Components by boiling point 5-4, 5-5, 5-6 (pages 92-96) Thurs Sept 29 Lecture 8; Quiz 4 Thurs Sept 29 1-Bromobutane pages Macroscale (page 263) Thurs Oct 4 Tues Oct 4 Thurs Oct 6 Thurs Oct 6 Finish 1-bromobutane MIDTERM EXAM Covers material through 1-bromobutane MAKE-UP PERIOD Tues Oct 11 Lecture 9 Tues Oct 11 Benzaldehyde from Benzyl Alcohol pages Handout. J. Chem. Ed., 1978, 55, 410. PCC is a carcinogen. You MUST wear the protective gloves provided, and dispose of all chemicals properly Thurs Oct 13 Lecture 10; Quiz 5 Thurs Oct 13 Aldol Condensation pages macroscale (pages ) Tues Oct 18 Lecture 11 Tues Oct 18 Finish aldol condensation and begin Diels-Alder Diels-Alder Handout; pages Experiment: J. Chem. Ed., 1990, 67, 525. Tues Oct 20 Tues Oct 20 Finish Diels-Alder Tues Oct 25 Lecture 12 Tues Oct 25 Acetylsalicylic acid pages Macroscale (pages ) Thurs Oct 27 Lecture 13; Quiz 6 Thurs Oct 27 Multi-step Synthesis pages Benzoin Condensation-Macroscale (pages ) 55-Synthesis of Heterocycle-Macroscale (pages ) KCN is a poison. You MUST wear the protective gloves provided, and dispose of all chemicals properly Tues Nov 1 Tues Nov 1 Thurs Nov 3 Thurs Nov 3 Continue multi-step synthesis Finish multi-step synthesis; MAKE-UP PERIOD 4

5 Thurs Nov 8 Lecture 14 Thurs Nov 8 Aldehydes and Ketones (Ch 36) pages Identify an unknown and prepare At least one derivative Tues Nov 10 Lecture 15; Quiz 7 Tues Nov 10 Nitration of methyl benzoate pages Microscale (pages ) & Tues Nov 15 Lecture 16 Tues Nov 15 Grignard Reaction pages Macroscale (pages ) immediately followed by 38-6-Macroscale (pages ) Thurs Nov 17 Thurs Nov 17 Tues Nov 22 Thurs Nov 24 Grignard continued No Class (Thanksgiving recess) No Class (Thanksgiving recess) Tues Nov 29 Lecture 16; Quiz 8 Tues Nov 29 Wittig Reaction pages Microscale (page 481) Thurs Dec 1 Lecture 17 Thurs Dec 1 Polymers pages Microscale (pages ) Tues Dec 6 Tues Dec 6 Tues Dec 8 Tues Dec 8 MAKE-UP PERIOD Lecture 18 (Questions, Check-out Protocol) HAND IN NOTEBOOK CLEANUP & CHECKOUT FINAL EXAM DATE WILL BE SET BY THE UNIVERSITY SCHEDULING OFFICE. 5

6 Laboratory Notebooks for Chem Purchase bound LABORATORY NOTEBOOK. Spiral or loose-leaf notebook is not allowed. Pages must be numbered sequentially. 2. Writing must be in ink. Do not use a felt tip pen that has water-soluble ink. 3. Create a TABLE OF CONTENTS for the notebook. Preferably keep the first two pages of your notebook blank with the heading CONTENTS written on each page. If you are numbering pages in your notebook, the next page after this will become page 1 and will be the page on which you write your first experiment. As you do each experiment, you will enter the heading in the table of contents along with the page number(s) on which the experiment is to be found. 4. Each experiment must be started on a new page. A descriptive title must be on the first line. Fill the pages sequentially as you complete the experiment. Do not skip lines with the intent of filling them in later. 5. Separate the parts of each experiment under various headings, such as Pre-lab or Procedure, Experimental, Discussion, and Conclusions. Procedure or Pre-lab section should include information that you can refer to as the experiment progresses. It could include important properties of the compound being used, structures, solubilities, etc. You might draw the picture of the apparatus you will use. Experimental is a detailed description of what you actually did and saw in the laboratory. This section must be complete. Your Experimental should have enough information for someone to do the experiment. If not, your experimental is not well written. Discussion and Conclusions are information such as the structure of the unknown, which you have deduced from the experimental data. A comparison of your calculated yield and theoretical yield is an important item for this section. If your yield is drastically low, you should attempt to identify (or speculate) the reason in the conclusions. 6. Immediately after conclusion of the experiment, you should date and sign the experiment. Your TA should sign as a witness. If the experiment is not finished, you may continue the next day by adding to the writing that you have done the previous day, and adding an additional set of signatures at the conclusion of the next day s work. 6