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CHEM 232 ORGANIC CHEMISTRY LABORATORY I

Fall Semester 2015 Laboratory Schedule


#

Week

Experiment

Lab Report Due Date

Aug. 31-Sept. 4

Literature and References Workshop

Sep. 8-11

Policies and Procedures; Lab Safety; Check-in, Academic Integrity

Sep. 14-18

Experiment #1 Recrystallization of Impure Solids


Reading: Pages 91-99 (recrystallization) and 36-39 and 111-115 (melting point)
Experiment: Pages 101-103 (Choose #1, #2 or #3)
Scale everything to only 0.5 g of solid (half of the described procedures)

Oct. 6
--Sept. 21-25

Paddias Reading: 119-127; 26-30


3

Sep. 21-25

Experiment #2 Extraction of Trimyristin from Nutmeg


Reading: Pages 79-81 (reflux) and 173-174
(5th edition: 171-173)
Experiment: Pages 174-175
(5th edition: 174-175)
Scale to 0.2 g of nutmeg do not distill after filtration

Sept. 28 Oct. 2

Paddias Reading: 128-131


4

Sep. 28-Oct. 2

Experiment #3 Base/Base Extraction


Oct. 5-9
Reading: Pages 75-81 and 155-163
(5th edition: 75-81, 153-161)
Experiment: Pages 164-165 (Procedure B)
(5th edition: 161-163)
Scale to 0.4 g of the mixture of benzoic acid, 2-naphthol and naphthalene
Paddias Reading 128-140

Oct. 5-9

Experiment #4 Separation of Spinach Pigments by TLC


Reading: Pages 179-184
(5th edition: 179-184)
Experiment: Pages 185-186
(5th edition: 184-186)
Paddias Reading: 162-172

Oct. 12-16

Oct. 12-16

Experiment #5 Separation of Fluorene and Fluorenone by


Column Chromatography
Reading: Pages 189-192
(5th edition: 188-192)
Experiment: Pages 193-194
(5th edition: 192-194)
Use a large pipet as a column, fitted with tubing and pinch clamp to regulate flow.
Use only ~50 mg of the solid mixture

Oct. 19-23

Paddias Reading: 172-177


7

Oct. 19-23

Experiment #6 Simple and Fractional Distillation


Reading: Pages 125-127; 129-130; 133-138
(5th edition: 127-129; 131-132; 135-140)
Experiment: Work in pairs one person performs a simple distillation
(131-132), the other performs a fractional distillation (141-142); both students
will use 10 mL of the same cyclohexane/toluene mixture of unknown
composition; Collect 1mL samples of the low and high boiling components from
each type of distillation
(5th edition: 133-134 for simple distillation; 141-142 for fractional distillation)

Oct. 26-30

Paddias Reading: 141-150


8

Oct. 26-30

Experiment #7 GC analysis of Distillate and


Mid-Term Exam (Experiments 1 5)
Reading: Pages 196-206
(5th edition: 196-206)
Experiment: Pages 206-207 (GC) and 207-208 (Response factors)
Design an experiment to determine the relative response factors of
toluene and cyclohexane
(5th edition: 206-208)

Nov. 2-6

Paddias Reading: 179-187


9

Nov. 2-6

Experiment #8 An SN2 Reaction Preparation of 1-Bromobutane


Reading: Pages 459-465
(5th edition: 461-467)
Experiment: Pages 465-468
(5th edition: 467-469)
Scale procedure down for a 25 mL round bottom flask
Paddias Reading: Pages 191-193

Nov. 9-13

10

Nov. 9-13

Experiment #9 Elimination with Alcoholic Potassium Hydroxide


Reading: Pages 331-334
(5th edition: 337-340)
Experiment: Pages 334-337
(5th edition: 340-343)
Work in pairs; scale by half for a 25 mL round bottom flask

Nov. 16-20

Paddias Reading: Pages 191-193


11

Nov. 16-20

Experiment #10 Radical Chlorination of 1-Chlorobutane and GC


Analysis of Experiment #9
Reading: Pages 196-206 (GC) and 309-312 (Chlorination)
(5th edition: 313-316)
Experiment: 206-207 (GC) and Pages 313-314 (Chlorination)

Nov. 2-6

Paddias Reading: Pages 191-193


November 23-27

12

Nov. 30-Dec. 4

NO LABS SCHEDULED & NO LAB REPORTS DUE

Experiment #11 GC Analysis of Experiment #10 and IR workshop


Reading: Pages 196-206 (GC) and Pages 235-258 (IR)
Experiment: Pages 206-207 (GC) and 207-208 (Response factors)
You may assume all dichlorobutanes have the same response factor
IR workshop documents are on CANVAS

----------

Dec. 07 - 11

For IR (4th edition: 237-261)


Paddias Reading: Pages 66-76
13

Dec. 7-11

Check-out

Dec. 14

Lab Final Examination (Experiments 6 11 & IR spectroscopy) - Room and time to be announced

Lab reports are due to your TA as you enter the lab at the beginning of the next lab period. Lab reports submitted after
this time will not be accepted for a grade.