CEM 255: Organic Laboratory Spring 2019 Lectures: Thursday 4:10-5:00 pm N130 BCC

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1 EM 255: Organic Laboratory Spring 2019 Lectures: Thursday 4:10-5:00 pm N130 B Instructors: Dr. Ardeshir Azadnia Office: 128 hemistry azadnia@chemistry.msu.edu Office hours: Mondays and Thursdays 10-11:30 am or by appointment Mr. Dave Voss Office: 134 hemistry voss@chemistry.msu.edu Office hours: by appointment lass Website: www2.chemistry.msu.edu/courses/cem255/

2 equired Materials Lab Text: EM 255 Organic hemistry Laboratory Manual 8th Edition", A. Azadnia, ayden- McNeil Publishing, Inc., 2018 Safety Supplies: Approved splash proof safety goggles (ANSI ) and lab coats are required. A rubber/latex/nitrile gloves are also encouraged. Supplementary eadings: A text, Any Organic hemistry Text Miscellaneous: Any bound notebook with duplicate pre-numbered pages and carbon paper (comes as a bundle with the lab manual). The perforated carbon copies will be torn out and submitted at the end of each lab. Also, a ballpoint pen (not pencil) is needed for lab reports. ourse Description: Material covered in lecture courses is based on experimental data accumulated over the years, which has been systematized into natural laws and theories. owever, the study of chemistry (or any science) requires that you learn some laboratory techniques and methods of data acquisition. It is intended that the skills acquired in this course will be of practical value to you in your fields of interest. It is hoped that a "hands on" experience also will enable you to grasp the concepts presented in EM 252 lecture more readily.

3 Grading There will be a 10 point of extra credit for lab clean up on Friday, April 26, Personal Protective Equipment (PPE): there will be a 10 points penalty for each experiment you don't have your lab coat on.

4 Absences Because our teaching staff is being used to capacity, there will be NO MAKE-UP LABOATOY, except for special circumstances, which will be decided on an individual basis. If you are unavoidably absent from a laboratory class due to illness or family crisis, contact Dr. Azadnia as soon as possible. A grade of zero will be assigned for an experiment missed regardless of the reason. owever, you may be allowed to make up the missed lab so long as you make arrangement with Dr. Azadnia within a week of the corresponding experiment. Students who miss three or more sessions due to illness, etc. should drop EM 255 and re-enroll another term. Incomplete grades ANNOT be issued when three or more labs have been missed. If you drop EM255 course, you still must be checked out of lab by your lab TA, on or before your last scheduled lab section. Failure to check out properly costs $25.00 plus breakage charges. No EM 255 lockers will be shared. If you believe someone has access to your locker, exchange your lock at the stockroom (room 133).

5 Write-ups Your Lab Manual is not to be used in the lab. You must work from your own procedures written in your lab notebook. An important laboratory skill is the making and writing down of precise observations. A well-kept notebook is an essential part of any investigation. Your notebook should be a complete description of what happened, or didn't happen, in your experiments. If someone else could repeat your experiment and get identical results using only the notebook for directions, then your notes are thorough. A well-kept set of records is an essential part of any investigation. Take notes as if you expected to repeat the work next term using only your own notes. Before entering the laboratory, you should familiarize yourself with the experiment by studying the Lab Manual and the corresponding chapter in your organic textbook. Experience has shown that those students who rewrite the procedure as numbered, single operation steps directly in their notebooks encounter fewer problems. If this is done in advance, then only observations and changes must be recorded during the experiment. Keep track of your progress by checking off the steps as you do them. arbon copies of all prelab and in-lab write-ups are to be submitted, along with any products, as you leave the laboratory.

NO skirts) Safety Goggles must ALWAYS be worn in

7 Laboratory Safety egulations 1. DESS ODE Firm footwear is required (NO sandals, NO open-toed shoes) Long pants that cover the entire leg must be worn at all times (NO shorts, NO skirts) Safety Goggles must ALWAYS be worn in the lab The dress code will be strictly enforced! Lab oats are required!

8 Laboratory Safety egulations 2. SAFETY EQUIPMENT Every student MUST do all they can to prevent accidents in their own work and they must be prepared for accidents by knowing in advance what emergency aids are available. The laboratory is equipped with several type of safety equipment and it is essential that you become familiar with the location and the operation of these tools. a. Emergency Shower: There is an emergency shower located on the hallway. It is for use when corrosive liquids have spilled over large areas of clothes and skin, or when clothing is on fire. b. Eye Wash Stations: The laboratory is equipped with eye wash stations. These stations dispense water and provide thorough irrigation of the eyes and face in the event a person is splashed with an irritating chemical. The contaminated body part should be rinsed for a minimum of 15 minutes. c. Fire Extinguisher: The fire extinguisher is located outside the laboratory. Know its location and how to operate it. It is very effective for fires involving organic liquids and electrical fires. If a fire extinguisher is used it must be given to the laboratory coordinator for recharging. Small fires in test tubes, beakers etc can usually be smothered by covering with a watch glass. In any case, EPOT any accident to your instructor immediately

9 Laboratory Safety egulations 1. Absolutely NO EATING or DINKING is permitted in the lab. 2. Waste Disposal Please place the waste materials in the appropriate containers. If you are unsure, make sure you ASK your instructor. For this lab you should expect to have both Inorganic and Organic waste, placed separately in different containers inside the last fumehood. Broken glassware belongs in the BOKEN GLASS bucket 3. No cell phones or listening to music in lab

10 Week 1 Melting Point Apparatus alibration Set at 3 Move to 4

11 Melting Point Apparatus alibration urve Ice Naphthalene Benzoic Acid Salicylic Acid Observed value ( o ) Literature value ( o ) Literature Value ( o ) points Full redit Observed Temperature ( o )

12 Using the alibration urve Literature Value ( o ) Observed Temperature ( o )

13 Molecular Models: onformational Isomers otate ing-flip Br Br Axial bromocyclohexane Equatorial bromocyclohexane

Molecular Models: Stereoisomers (a) (b) 3 O O 2 O 2 3 O 1 O 2 O 2 2 1 O

14 Molecular Models: Stereoisomers (a) (b) 3 O O 2 O 2 3 O 1 O 2 O O 2 O 3 3 configuration ( )-Lactic acid 3 3 S configuration (+)-Lactic acid

15 Molecular Models: Stereoisomers Stereoisomers (Section 4.2) are compounds whose atoms are connected in the same order but with a different spatial arrangement. Among the kinds of stereoisomers we ve seen are enantiomers, diastereomers, and cis trans isomers of cycloalkanes. Actually, cis trans isomers are just a subclass of diastereomers because they are non mirror-image stereoisomers: Enantiomers (nonsuperimposable mirror-image stereoisomers) 3 O 2 O O 2 O 3 ()-Lactic acid (S)-Lactic acid Diastereomers (nonsuperimposable non mirror-image stereoisomers) onfigurational diastereomers O 2 N 2 3 O 2,3-2-Amino-3- hydroxybutanoic acid O O 2 N 2 3 2,3S-2-Amino-3- hydroxybutanoic acid

16 Molecular Models: Meso ompounds Symmetry plane Not symmetry plane rm. 3 O 2 3 O O 2 O O O O 2 Symmetry plane O O 2 Propanoic acid (achiral) 3 O 2 Lactic acid (chiral) Symmetry plane * 1 O Methylcyclohexane (achiral) 2-Methylcyclohexanone (chiral)

17 Staggered Gauche Staggered Anti Eclipsed Molecular Models: Newman Projection Eclipsed conformations kj/mol Energy

2 2 1 2 3 6 (c) (b) Observer 1 2 3 4 5 6 5 4 Staggered

18 (c) (b) Observer Staggered Gauche Staggered Anti Eclipsed Molecular Models: Newman Projection

19 Molecular Models: Fischer Projection A tetrahedral carbon atom is represented in a Fischer projection by two crossed lines. The horizontal lines represent bonds coming out of the page, and the vertical lines represent bonds going into the page. Press flat W Z Y X W Y Z X W Z Y X Fischer projection For example, ()-glyceraldehyde, the simplest monosaccharide, can be drawn as in Figure O O 2 O O = = O 2 O Bonds out of page O O 2 O Bonds into page O O 2 O ()-Glyceraldehyde (Fischer projection) L-Glyceraldehyde [(S)-( )-glyceraldehyde]

20 Molecular Models: Fischer Projection Press flat W Z Y X W Y Z X W Z Y X Fischer projection Mirror O O O O O O 2 O O = = O 2 O Bonds out of page O O 2 O Bonds into page O O O 2 O O O O 2 O ()-Glyceraldehyde (Fischer projection) L-Glucose (not naturally occurring) D-Glucose

De Anza College Chemistry Department Spring 2018

De Anza College Chemistry Department Spring 2018 COURSE TITLE Chemistry 1A-01 & 02 General Chemistry Class 04/09/18 to 06/28/18 Meeting times: Sec 01/02 Lecture 11:20 AM 12:20 PM, MWF, Room SC1102 Sec