Instructor: Dr. A. D. Bacher
Office: Young Hall 3077E
Phone: (310)82-51853
Email: bacher@chem.ucla.edu
Web page: www.chem.ucla.edu/~bacher
Course discussion board: https://piazza.com/ucla/winter2016/chem30cl/
Office hours: MWF 10-11 am, M 3-4 pm and TR 11-12 pm or by appointment (in YH 3077E)
Lab Rooms: YH 6072, YH 6086

Safety

Safety glasses are to be worn at all times in the laboratory. A knee-length flame-resistant lab coat must be worn while in lab (lab aprons, polyester and cotton lab coats are not acceptable). Contact lenses should not be worn in the laboratory. Low-heeled shoes, which cover the toe and instep, must be worn at all times while in the laboratory. Clogs, sandals, cloth-top sneakers and narrow-base heels are not acceptable. Tennis shoes will suffice. Shorts are not allowed. Pants that cover the ankles are required. Hair that is shoulders length or longer has to be tied back. Food, chewing gum and cell phones are not allowed in the laboratory. Any student under the care of a physician for either acute or chronic medical reasons (i.e. diabetes, essential hypertension, epilepsy, pulmonary disease) and/or is pregnant should advise his/her physician that s/he is taking organic chemistry lab. Also, the student should advise the Lab Instructor immediately.

Glass and syringe needles are never to be disposed of in the regular trash receptacles (this poses a hazard to the janitor). All glass waste and syringe needles go into the glass waste containers (blue box labeled glass waste). Failure to observe this rule will result in dismissal from the course. Any student whose deliberate or negligent acts or omissions endanger his/her own safety or that of others may be expelled from the laboratory. Lab safety will be discussed at the first lab lecture.

All experiments have to be conducted under the hood. This also applies to filtrations. Solvents have to be removed using the rotary evaporator. The teaching assistant will demonstrate on how to use this piece of equipment. Do not break the bump trap unless you want to pay for it.

Glass and syringe needles are never to be disposed of in the regular trash receptacles (this poses a hazard to the janitor). All glass waste and syringe needles go into the glass waste containers (blue box labeled glass waste). Failure to observe this rule will result in dismissal from the course. Any student whose deliberate or negligent acts or omissions endanger his/her own safety or that of others may be expelled from the laboratory. Lab safety will be discussed at the first lab lecture.

Wait Listed

If you are wait-listed, wait inside the lab section you are wait-listed for. If there is space you will be added. The department (Denise Mantonya, Young 4009) will add you if you are written in on the class roster (make certain that you are written in). Regardless, it is your responsibility to make certain that you have been added to URSA. If your name doesn't by the thursday of the second week of your enrollment, contact the instructor before the last day to add. The department does not use PTE numbers anymore.

Text

Course Reader Chem 30CL and Exam Collection for Chem 30CL (package for $36, Winter 2016 edition) are required; "A Survival Kit for the O=Chem Lab" ($29, Winter 2016 edition)is highly advisable if you do not own arecent version of this reader, they are available from Course Reader Materials starting December 11, 2015); Mohrig, Techniques in Organic Chemistry, 4th edition (recommended).; Brown and Foote, Organic Chemistry, 7th edition (or a comparable O-Chem text book).

Lab Notebook, Glasses, Nitrile Gloves & Coat

Bound or spiral with duplicate (a must!) removable pages, safety glasses, lab coats, nitrile gloves are available from AX
S (Young 1275), the ASUCLA bookstore or the medical bookstore. You will not be permitted to conduct an experiment without proper clothing, starting meeting 1.

Handouts and Lecture notes

Additional lecture handouts will be available on the course web site. If you are unable to attend lecture then you need to make arrangements with a classmate or friend for those days notes and handouts. The lecture will also be podcasted. It is advisable to consult the web site for additional information about techniques used in the lab. Note that the instructor does not use the CCLE website since he has his own website on which materials will be posted.

Academic Standards

Attendance to the lab course lecture is mandatory, and not only because the quizzes will be administered in the lecture. You will be held responsible for all material covered during lecture. On occasion, adjustments to the course syllabus during lecture may be made (e.g., change of exam date, lecture material to be covered, etc.). An unexcused failure to attend lecture or to perform experiments on schedule or to submit timely experimental write-ups may have an out of proportion adverse effect on your course grade. In extreme cases, the student may receive an "F"-grade for the course regardless of the point total. Failure to turn in a laboratory notebook at the end of the term will result in a failing grade.

Failure to perform an experiment or submit a report will result in an automatic "F"-grade for the course. In the case of an excused absence, the student will be allowed to makeup the experiment without penalty (if you are unable to makeup the experiment you will receive an Incomplete). Falsely representing that an experiment has been performed will be regarded as equivalent to cheating on an exam and will be reported to the Dean of Students.

Examination/Quiz Policy

There will be no make-up exams or quizzes. No exams will be administered earlier or later than the scheduled exam time. If the final exam is missed, the student should bring it to the immediate attention of the instructor. If the student has a good reason then they will receive an incomplete for the course, otherwise, they will receive an automatic failure grade (F) for the entire quarter. An established incident of cheating will also result in an automatic failure grade (F) for the entire quarter. Students who are aware of cheating are encouraged to report such incidents. Securing a "recommendation" after a cheating incident at the University is, needless to say, awkward at best! Do not foolishly mortgage your professional future by cheating now. A course grade of incomplete (I) will be considered only for individual cases with exceptional extenuating cause. An incomplete will not be given in lieu of a failing grade i.e., because you failed the final exam.

Lab Preparation

You need to be prepared for the experiment before you come to lab if you wish to complete the experiment in the time allotted. There is no make-up time in the course and no space for you to work in other sections. Also study the pertinent sections in the text and then prepare a summary or flow chart of the procedures that will be performed in the laboratory. Your teaching assistant will check your pre-lab preparation before you are allowed to begin any experiment. An open laboratory text will result in an automatic 10 point deduction. For purposes of safety, lack of preparation will result in dismissal from that lab period.

Grading

During the first meeting, your TA will briefly discuss lab report format and answer any questions you have concerning this matter (i.e., pre-lab and post-lab write-ups). Each experiment must be written up, in a bound notebook in ink, before coming to lab, including the summary and/or flow chart of the work to be performed. Typed reports or word processing is not allowed (except for the formal report for the multistep synthesis -- use a lab notebook! The first two pages of your lab notebook should be reserved for a table of contents. TA/Instructor evaluation points will be assigned at the end of the course (5 point per lab meeting). Following is the point break down for each lab report.

In-Lecture Quizzes: ~10-15 minutes (closed book and notes; ~3-5 questions; quiz will cover previous and current week's experiments, 20 points each). Quiz schedule will be announced in class and on the web site. Make sure that you come on time, otherwise you will not be allowed to take the quiz. No exceptions. Note: Lowest or one missed (regardless of the excuse) quiz will be dropped.

TA evaluation (product evaluation, in-lab evaluation, preparedness) 10 points/lab

Your teaching assistant will spot check the pre-lab and post lab write-ups. 5+5 points/lab

Formal Report (graded by instructor) (Draft version (20 points) + Final version (60 points))

Proposal for Ferrocene project (20 points)

Oral Presentation (20 points)

Lab Notebook** (end of quarter evaluation of lab notebook) (20 points)
** must be bound with consecutively numbered pages and in ink; if a bound lab notebook is not used (i.e., spiral notebook; word processing generated report; ring note book) then no points will be given; if a table of contents is missing then there will be a 20 point deduction; missing homework assignment(s) will result in deduction of 5 points per lab; notebooks that are well-organized and complete will receive full credit Failure to hand in a lab notebook, at best will result in an incomplete and in unexcused cases will result in a non passing grade.

Final Product evaluation:

Epoxidation (20 points)

Lidocaine (20 points)

Final Exam (March 17
, 2015, 8:00-11:00 am) (~40 % of grade, has to be passing grade meaning more than 50 %)

Lecture attendance: (mandatory) - 5 points/absence

Housekeeping, labeling, safety, etc. -5 pts/each

Housekeeping

The laboratory can function smoothly only if left clean at the end of each lab. On leaving the lab, after an experiment, each student at his/her station and hood used should ensure the following:

1. Hot plate is unplugged and cord is neatly coiled around plate. Vacuum trap is emptied, cleaned and clamped. if not then -2 points

2. Work bench area needs to be sponged down at the end of lab. if not then -2 points

3. Spills are wiped up and balances are swept clean. if not then -2 points

4. The sink is free of glass, paper towels, corks and other insoluble solid refuse.
Such material belongs in the appropriate waste can. if not then -2 points

Poor house keeping will result in a grading penalty of 1-5 points for each infraction. Dumping of hazardous material in trash receptacles or in sinks is ground for dismissal from the course.


Waste Disposal

All chemical waste goes into the appropriate waste containers supplied in the hood. If you are not sure of how to dispose of a chemical, ask your TA or stockroom personnel for help. All products are to be stored in a labeled container. All vials (storage containers) containing product must be labeled correctly. Failure to label properly (name, compound, date) a vial will result in a 5 point deduction.


Breakage & Check-out

The security of your locker is your responsibility. You will be charged for broken or missing items; your desk must be fully stocked on checkout. If you fail to checkout of a desk you have drawn, you will be assessed a $25.00 abandoned desk penalty in addition to charges for missing or broken equipment.

If you break instruments or equipment due to negligence and/or not following the procedures, you will fully held financially responsible. Failure to report these things immediately will lead to an automatic dismissal from the course. However, there is no reason to be scared of breaking things, but you should take precaution to avoid major accidents.

Meeting 1-8
Synthesis of Jacobsen's Catalyst and Epoxidation

Chiral Resolution

Synthesis of an Diimine (Jacobsen's ligand)

Synthesis of a transition metal catalyst (Jacobsen's Catalyst)

Epoxidation of an Alkene using a chiral catalyst

NMR spectroscopy

GC on chiral Column

Literature work

Formal Report

GC/MS and HPLC tutorial?
Meeting 9-11
Synthesis of Lidocaine

Lidocaine1
Reduction

Synthesis of an Amide

Nucleophilic Substitution

Meeting 12-14
Synthesis of Nitrobiphenyls

Nitration1

Suzuki-Miyauri  Reaction

Esterification

Nitration

Meeting 15-18
Synthesis of Ferrocene derivatives

Organometallics

Friedel-Crafts-Acylation

Proposal

Oral Presentation

Please read also the Course philosophy and the Rules and Hints for the Laboratory Work.