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LABORATORY COURSE PACKET CHEM 2312 ORGANIC CHEMISTRY 1 Fall 2019

Packet contains the following: 1) 2) 3) 4) 5) 6)

Laboratory textbook, notebook, and check-in information. Grading policies. Experiment schedule. Laboratory syllabus and assigned reading. One copy of the Laboratory Safety Agreement. Protocol for first experiment.

All organic chemistry labs will first meet the week of September 16 (at their respective times and days) in room 324 Hurtig Hall.

ORGANIC CHEMISTRY LABORATORY ALL SECTIONS TEXTBOOKS:

James W. Zubrick, The Organic Chem Lab Survival Manual, Wiley, Tenth Edition, 2016 L.G. Wade, Jr., Organic Chemistry, Pearson, Ninth Edition (This is the same textbook used in the organic chemistry lectures)

NOTE: Come prepared to work. This packet contains all the information you will need for your first experiment.

LABORATORY CHECK-IN Please report to room 324 Hurtig for laboratory check-in on your assigned day and time. Be sure to check your course registration number for your exact time. You must have safety glasses the first week of laboratory. NO short clothing or open-toed shoes are allowed in the laboratory! LABORATORY NOTEBOOK: You are to maintain a laboratory notebook in this course. You must select a notebook that makes “carbon copy” pages of your writings that can be removed. A satisfactory notebook may be obtained from the Bookstore. The original copy page remains as your record while the copy is turned in to your laboratory instructor for their records. All work should be entered directly into the notebook in INK. No notes should be taken on scrap paper. All errors should be crossed out with ONE line, so that they remain legible. Before coming to the laboratory, you should prepare by doing any of the assigned reading for that experiment. Some of this reading will be review as you move through the course. During an experiment you should record in the lab notebook: (1) (2) (3) (4) (5) (6) (7) (8)

The experiment name The date Statement of experimental objectives All observations (step by step account of what you did and its result, if any) Raw data Summary of experimental results Balanced equations for all significant reactions Modifications to the experiment

Notebook Quiz: A well-kept lab notebook should enable another person to reproduce the exact conditions under which an experiment was performed. As such, there may (or may not) be an extra credit notebook quiz given during the semester that asks detailed questions about experiments performed earlier in the term. The notebook would be the only reference material allowed during the quiz.

Lab Report: Format and Grading Policies General Comments: This lab course is designed to teach you the basic techniques used on a daily basis in organic research labs for the synthesis and purification of organic compounds. Grading format: There are 7 lab reports per term and 10 points available per report. There are also 10 points available for your equipment’s condition at the term’s end and 20 points for performing hygiene officer duties once during the semester (100 point total for the term). A 94-100 A- 90-93 B+ 87-89 B 84-86 B- 80-83 C+ 77-79

C CD+ D DF

74-76 70-73 67-69 64-66 60-63 0-59

Lab Report Format:

The 10 points per lab session are awarded via the submission of a weekly lab report. Lab reports must be TYPED and passed in to your TA by the start of the next lab session. Lab reports must contain: 1.

TITLE PAGE: Must contain your name, your TA’s name, the date of the experiment’s performance, the date the lab report was submitted, and the title of the experiment.

2.

OBJECTIVE: Briefly explain the goal of the experiment in your own words. It should detail how the goal will be met and what techniques will be utilized.

3.

REACTION EQUATIONS: All reagents, products, and reaction conditions should be shown in a balanced equation. Do not include a reaction mechanism unless it is specifically requested by your TA. This section may be written-in by hand.

4.

THEORETICAL YIELD: Calculate your theoretical yield by way of the amount of limiting reagent, which should be specifically identified, actually used (i.e. if your protocol says to use 0.50g of benzil, your limiting reagent, and you measure out 0.49g of benzil, use 0.49g to calculate theoretical yield). Show all your work. This section may also be written-in by hand.

5.

PROCEDURE: The procedure must be in your own words (do not just copy the protocol) and should be a short paragraph detailing the general order of operations.

6.

OBSERVATIONS: What you actually did in lab and what you observed (color changes, etc). It should be written in third person past-tense (no “I”, “We”, or “They”). Deviations from the protocol and how any problems were corrected should also be noted.

7. CHARACTERIZATION: Percent yield (may be hand-written, show all work), the physical description of the final product, and the results and analysis (purity, identification) of any characterization (melting-point, FTIR, NMR, TLC) should all be included in this section.

8. CONCLUSION: This section should include an analysis of the generated data, whether or not the results were as expected, and whether there were incidents during the experiment that could have had negative effects on the yield or purity of the product. Don’t repeat previous sections unless it is necessary for clarity.

Lab Report Grading Scheme The 10 lab report points will be awarded under the following criteria: 4 Points: Level of Completion—To receive full credit, the lab report must contain each and every applicable section detailed in the “Lab Report Format” description above. 4 Points: Level of Correctness—Full credit requires all chemical equations and calculations to be correct and for all conclusions to be valid for the given data. 2 Points: Level of Organization and Expression—Thoroughness, a high level of clarity, and an economy of words are all necessary to receive full credit. The report should be in the student’s own words and resources must be cited. Neatness (or lack thereof) is also taken into consideration. Point Deductions Point deductions may take place in the lab report, but points may also be lost during the experiment itself. Certain behavior is expected in the organic chemistry labs--you will not receive credit for this behavior, but points will be deducted from the 10 point lab report if you don’t follow the rules. 1 Point: Punctuality--If you aren’t on time, you could miss important safety information and you’ll tie up your TA with questions they answered during the pre-lab lecture. Depending on how late you are, you may or may not be allowed to perform the experiment. 1 Point: Laboratory Safety--Failure to wear safety equipment or purposefully engaging in unsafe activity will result in a point deduction. This deduction can occur more than once per lab. 1 Point: Chemical Hygiene--Improper disposal of hazardous waste or failure to leave a clean lab station at the experiment’s end (spills or dirty glassware) will result in a point deduction. Failure to fulfill Hygiene Officer responsibilities will also result in a deduction. 1 Point: Professionalism--This is a broad category where point deductions can take place for behavior such as talking (or beginning the experiment) while the TA is lecturing, being a disruption in the lab, or not making a good-faith effort to complete the lab successfully. Point Deduction Example: You received 10/10 points on the lab report, but were late to lab and received a 1 point deduction. Your recorded score for the lab would be 9/10.

Missing a Lab There are no lab make-ups. If you know that you will need to miss a particular lab day (for a valid reason such as an interview), let the lab staff know as soon as possible. If you miss a lab due to illness, email John Bottomy ([email protected]) the day you miss lab. Retroactive excuses or appointments that happen to fall near holidays will be thoroughly scrutinized— in order to be excused for the absence, documentation (medical) will be required and you will need the signature of both a lab staff member and the Department Chair of Chemistry and Chemical Biology. Holiday travel plans do not constitute an excuse.

Cheating and Plagiarism Turning in work that is not your own cannot be tolerated and could lead to your dismissal from Northeastern following an investigation by the Office of Student Conduct and Conflict Resolution (OSCCR).

Experiment Calendar Fall 2019 CHEM 2312

Experiment

MON

TUE

WED

THU

FRI

1) Lab Safety and Check In

Sep 16

Sep 17

Sep 18

Sep 19

Sep 20

2) Crystallization and Melting Poi nt

Sep 23

Sep 24

Sep 25

Sep 26

Sep 27

3) Thin Layer Chromatography

Sep 30

Oct 1

Oct 2

Oct 3

Oct 4

Oct 7

Oct 8

Oct 9

Oct 10

Oct 11

5) Separation and Purification of Components of an Analgesic Tablet

Oct 21

Oct 22

Oct 23

Oct 24

Oct 25

6) Distillation and Boiling Point

Oct 28

Oct 29

Oct 30

Oct 31

Nov 1

7) Nucleophilic Substitution Reactions of Alkyl Halides

Nov 4

Nov 5

Nov 6

Nov 7

Nov 8

8) Cyclohexene from Cyclohexanol

Nov 18

Nov 19

Nov 20

Nov 21

Nov 22

4) Extraction: Caffeine from Tea

No Labs on These Days: * Please Note: Labs are not scheduled for the weeks of Oct 14 (Columbus Day) and November 11 (Veterans Day)

LABORATORY ASSIGNMENTS – Organic 1: Lab 1: Check-in period and chemical hygiene and safety. Lab 2: Crystallization Reading: The Organic Chem Lab Survival Manual (henceforth simply “Zubrick”), read pgs 1-5 (Safety), 92-97 (Recrystallization, Gravity Filtration), 101-102 (Hirsch, Activated Charcoal, Water Aspirator) and 74-77(Melting Point) 80-82 (SRS Digimelt).

Lab 3: Thin Layer Chromatography Reading: Zubrick 199-212 (Chromatography, Thin-Layer Chromatography)

Lab 4: Extraction of from Caffeine Tea Reading: Zubrick 114-117 (Extraction), 68-71 (Drying Agents), 179-182 (Rotary Evaporator), 2224 (Calculation of Percent Yield).

Lab 5: Separation and Purification of Components of an Analgesic Tablet Reading: Zubrick 119-120 (How to Extract and Wash What), 128-130 (Extraction and Washing: Microscale).

Lab 6: Distillation and Boiling Points Reading: Zubrick 150-151, 155-156 (The Distillation Mistake), 164-167 (Fractional Distillation), 175-178 (Microscale Distillation).

Lab 7: Nucleophilic Substitution Reading assignments: Organic Chemistry (the textbook used in lecture, henceforth Wade) 261286

Lab 8: Cyclohexene from Cyclohexanol Reading: Alkene Synthesis by Dehydration of Alcohols: Wade 341-343. Zubrick Review Reading: 68-71 (Drying Agents) 22-24 (Calculation of Percent Yield).

Lab 9: To Be Announced Reading for Zubrick 10th Edition—see next page for 9th Edition

LABORATORY ASSIGNMENTS: Lab1: Check-in period and chemical hygiene and safety. Lab 2: Crystallization Reading: The Organic Chem Lab Survival Manual (henceforth simply “Zubrick”), read pgs 1-5 (Safety), 104-110 (Recrystallization, Gravity Filtration), 113-115 (Hirsch, Activated Charcoal, Water Aspirator) and 88-91(Melting Point).

Lab 3: Thin Layer Chromatography Reading: Zubrick 219-233 (Chromatography, Thin-Layer Chromatography)

Lab 4: Extraction of from Caffeine Tea Reading: Zubrick 128-131 (Extraction), 80-83 (Drying Agents), 195-199 (Rotary Evaporator), 2325 (Calculation of Percent Yield).

Lab 5: Separation and Purification of Components of an Analgesic Tablet Reading: Zubrick 134-135 (How to Extract and Wash What), 142-144 (Extraction and Washing: Microscale).

Lab 6: Distillation and Boiling Points Reading: Zubrick 164-165, 170 (The Distillation Mistake), 178-180 (Fractional Distillation), 191194 (Microscale Distillation).

Lab 7: Nucleophilic Substitution Reading assignments: Organic Chemistry (the textbook used in lecture, henceforth Wade) 261286

Lab 8: Cyclohexene from Cyclohexanol Reading: Elimination Reactions of Alcohols: Wade 341-343. Zubrick Review Reading: 80-83 (Drying Agents) 23-25 (Calculation of Percent Yield).

Lab 9: To Be Announced

Reading for Zubrick 9th Edition—see previous page for 10th Edition

NORTHEASTERN UNIVERSITY DEPARTMENT OF CHEMISTRY AND CHEMICAL BIOLOGY LABORATORY SAFETY AGREEMENT

1) EYE PROTECTION IS TO BE WORN AT ALL TIMES! You must purchase and wear safety goggles. Eyeglasses do NOT satisfy this regulation. Safety goggles must be worn OVER eyeglasses. In the event that you do not have safety goggles you may borrow a pair, in exchange for an I.D. All splashes to the eye must be cleaned out in the eyewash. 2)

LAB COATS ARE TO BE WORN AT ALL TIMES! Short clothing is NOT allowed in the laboratory. Closed toe shoes must be worn. Sandals are not allowed in the laboratory.

3) NITRILE GLOVES MUST BE WORN AT ALL TIMES! Gloves will be supplied. Latex gloves are not allowed in the laboratory. Remove your gloves each time you leave the laboratory. NEVER touch your eyes, face, or bare skin with gloves. 4) DO NOT POUR ANY CHEMICALS DOWN THE SINK! All chemicals and waste must be disposed of properly! There will always be a HAZARDOUS WASTE container located in one of the hoods. You must dispose of the chemicals in the appropriately labeled bottles. Mixing of wastes may produce toxic fumes or violent reactions. Please ask the lab instructor any questions about waste disposal. Waste bottles must be capped at all times and must remain in the gray secondary containment trays. 5) NO FOOD, CANDY, OR DRINKS ARE ALLOWED IN THE LAB AT ANY TIME! 6) UNAUTHORIZED EXPERIMENTS ARE NOT ALLOWED! All experiments must performed with a qualified instructor present. 7) EXPERIMENTS SHOULD NEVER BE LEFT UNATTENDED! If there is a need for you to leave the lab during an experiment lab personnel should be notified. Cellular phones are not allowed in the lab. 8) COMPLETELY CLEAN ALL GLASSWARE BEFORE STORAGE! Students are assigned their own instruments and glassware. Chemicals are NEVER to be stored in your drawer without the permission of the instructor. Any chemicals found in your drawer will be discarded. 9) BROKEN GLASSWARE MUST BE DISPOSED OF IN THE “BROKEN GLASSWARE” CONTAINERS. 10) REPORT ALL CHEMICAL SPILLS TO THE LAB INSTRUCTOR OR LAB PERSONNEL IMMEDIATELY, DO NOT ATTEMPT A CLEANUP! 11)

REPORT ALL INJURIES IMMEDIATELY! This includes chemical spills on you or somebody else. First aid kits are available in the laboratories.

Department of Chemistry and Chemical Biology Undergraduate Organic Chemistry Lab

Experiment title: Crystallization Organic technique and overview: Recrystallization is a technique used to purify solid compounds. Usually, it will be employed after synthesizing a compound and working it up (extraction, washing—concepts that will be covered later). At its simplest, recrystallization involves dissolving an impure compound in a hot solvent and then allowing the compound to come back out of solution as a solid as the solvent cools. The solid compound is then collected by filtering it from the solvent. If impurities remain dissolved in the solvent then presto-your compound is purer. The relationship between the solvent and the compound you want to purify is very specific —the compound must be relatively insoluble in the solvent when it’s cold and much more soluble in the solvent when it’s hot. If the compound dissolves easily in a particular room-temperature solvent, you don’t want to use that solvent, because the only way to retrieve your compound is to evaporate the solvent completely (which wouldn’t get rid of any solid impurities). If your compound and its impurities are both insoluble in a particular solvent (whether hot or cold), you shouldn’t use that for recrystallization either, as no purification can take place. When you’ve found a solvent that meets the recrystallization criteria (for your lab we have chosen compounds that all recrystallize well in water), it is important to remember that you want to dissolve your impure compound in a minimal amount of the hot solvent. It’s extremely easy to add too much solvent, and if that happens, you won’t get as much pure compound (or any compound sometimes) when you try to precipitate it by cooling the solvent down.

Goal of the experiment: Recrystallize an unknown compound and identify it by its melting point. Experiment protocol: You will be given an unknown compound in a bag containing decolorizing carbon, which must be removed before crystallization. Write down the number of your unknown in your lab notebook. 1. Heat 10 – 20mL of water to boiling in a 50 mL Erlenmyer flask on your hot plate. Have a boiling stick in the water to prevent bumping. 2. In a 50 mL beaker dissolve 250mg (0.250 grams) of the unknown sample in 10mL of the hot water. 3. Filter the charcoal out of the hot solution by gravity into a 20mL beaker. Use a glass funnel and a piece of 11cm filter paper. Wash the filter paper with another 1mL of hot water to push residual crystals into the beaker. 4. Allow the solution to cool for a few minutes and then cool the 20mL beaker in an ice bath for 5 minutes to induce crystallization.

5. If necessary (no crystals appear with cooling), reduce the volume of the hot solution approximately 20–30% by boiling off the water (boiling stick) on a hot plate. Attempt the cooling process from step 4 again. 6. Connect the thick walled vacuum tube to the aspirator side arm in your sink and connect the other end to a filter flask (which should be securely clamped). 7. Place a piece of filter paper (1.5cm) on top of a Hirsch funnel. Place the funnel atop the clamped filter flask. Turn on the water. Pour the crystal slurry from the 20mL beaker onto the filter paper in the Hirsch Funnel. 8. The crystals should collect on the paper while the liquid is sucked into the filter flask. Leave the crystals to dry in the Hirsch funnel for at least five minutes. 9. Disconnect the hose from the filter flask first and then turn off the water. 10. Get a large (11cm diameter) piece of filter paper and place the product on it. Fold the paper in half a few times so that the crystals are secure and leave it in the drawer (make certain you have recorded the unknown number on the sample packet and you’ve written your name on the filter paper containing your crystals). At next week’s lab, you will find the melting point of the compound to determine its identity. Compound Acetanilide Adipic Acid Benzoic Acid

Melting Point C 114 151-153 122

Solubility g/mL of water* 0.56335, 3.580 1.515 0.2718, 2.275

* Superscript indicates temperature of water during measurement.

Safety and waste disposal: Please dispose of all capillary tubes, filter paper, crystals, and residual solutions into their properly labeled containers....