Culbertson, Justin

English

SPARK: Scholarship at Parkland | Parkland College

Parkland College
Chemistry Courses Natural Sciences Courses
2015
Chemistry 201 Organic Chemistry I Laboratory
Spring 2015
Justin Culbertson
Parkland College, jculbertson@parkland.edu
Open access to this Course Materials is brought to you by Parkland College's institutional repository, SPARK: Scholarship at Parkland. For more
information, please contact spark@parkland.edu.
Recommended Citation
Culbertson, Justin, "Chemistry 201 Organic Chemistry I Laboratory Spring 2015" (2015). Chemistry Courses. Paper 36.
http://spark.parkland.edu/chem_course/36
Justin E Culbertson  Chemistry 204 
syllabus_S15.docx - 1 - January 8, 2015 
 
SPRING 2015 – CHE 204 
ORGANIC CHEMISTRY I LABORATORY 
 
INSTRUCTOR:   Justin E. Culbertson 
 
CONTACT INFORMATION: Office:  L 262 
    Phone:  (406) 836-7981 
    Text: (406) 836-7981 
    Email:  jeculbe2@illinois.edu     
 
OFFICE HOURS:  In L262:  M 7:00 – 8:00 PM 
I’m also available by appointment. 
 
LECTURE:      Section 002: M 6:00 – 6:50 PM in L216 
     
LABORATORY:  Section 002: W 6:00 – 9:00 PM in M228 
 
REQUIRED MATERIALS: Experiments for Organic Chemistry I, Illinois State University lab manual 
 Labs, Lab Reports, & Course Handouts, Parkland College lab manual 
 Duplicate page laboratory notebook and an ink pen 
 Lab safety goggles (glasses are NOT acceptable) 
 iClicker 
 
OPTIONAL MATERIALS: Organic Chem Lab Survival Manual, J. W. Zubrick, 9th edition 
  
COURSE SCHEDULE:  
The course schedule is available in Cobra Learning, where it will be updated as needed. 
 
COURSE DESCRIPTION: 
 Chemistry 204, Organic Chemistry I Laboratory, is a beginning organic chemistry laboratory course that teaches 
basic laboratory techniques (recrystallization, melting point, TLC, column chromatography, GC, refluxing, 
distillation, spectroscopy, etc.) and provides experience in performing simple organic reactions. 
 
PREREQUISITES: 
 Parkland College CHE 101 and CHE 102 or equivalent with a grade of C or higher and concurrent enrollment in 
CHE 203. 
 
GOALS: 
 Foundation – Know basic terms. Understand writing skills and experimental techniques required in an advanced 
organic chemistry lab. 
 Apply – Apply writing and experimental skills. Analyze and discuss experimental results. Manage small and 
large laboratory projects effectively. 
 Integrate – Connect information within this course, with the organic lecture courses, and with your life 
experiences. 
 YOUR Growth – Feel increasingly comfortable in a chemistry lab, working with a team of others. Increase 
interest in scientific experiments and/or applications. Reflect on and understand how you learn best in a 
chemistry lab course. 
 
ATTENDANCE: 
 Attendance at both the lecture and the lab sessions will be graded.  Lecture attendance will be based on your 
participation in clicker questions throughout the lecture period.  These questions will be graded on a completion 
basis only.  If you participate in all clicker questions during a lecture period, you will receive your full lecture 
attendance score. 
 
 
In order to successfully complete this class you MUST attend all labs.  In order for an absence to count as 
excused, you must provide a documented excuse for your absence (religious holiday, medical appointment, 
Justin E Culbertson  Chemistry 204 
syllabus_S15.docx - 2 - January 8, 2015 
approved college athletic activity or death in the immediate family).  If you are sick enough to miss lab then you 
are sick enough to go and see a doctor!  If at all possible, inform your instructor of any anticipated absences 
PRIOR to the absence. 
 
Anyone who does not follow the lab rules provided, including additional rules as stated by your instructor, may be 
asked to leave the laboratory.  If you are asked to leave lab, the lab will be counted as an unexcused absence.  In 
addition, lab penalties may be taken out of your lab attendance grade.  A list of penalties can be found on the 
Organic Chemistry Lab Rules handout.  Additional penalties may be determined on a lab by lab basis.  All 
penalties will be clearly stated before being applied. 
 
 Unlike other classes, most organic chemistry labs take three (3) hours to complete.  Therefore, you should never 
expect to leave lab early.  Also, anyone arriving late to lab will experience difficulty finishing his or her lab during 
the allotted time slot.  It is very important that you come to lab on time and ready to work.  Lab begins precisely at 
the time listed on the clock in the laboratory.  At the beginning of lab demonstrations and safety instructions are 
made.  Arriving even one minute late means that you missed part of this and your lab participation grade will be 
negatively affected.  If you arrive after the safety announcements you may not start the lab and it is considered an 
unexcused absence.   
 
There will be NO make-up labs.  You will receive a 0 for all assignments associated with any missed lab (lab 
attendance, pre-lab quiz, notebook – both prelab & lab record, and lab report).  Two unexcused absences from 
lab will result in an automatic F for the course. 
 
LAB NOTEBOOKS: 
How to keep a laboratory notebook properly is one of the most important skills to be learned in an organic 
chemistry lab.  During this semester an emphasis will be placed on how well you keep a lab notebook.  Both the 
structure and the content of the notebook will be evaluated.  An excellent reference for how to keep a lab 
notebook is The Organic Chem Lab Survival Manual, by J. W. Zubrick.  The most important aspects of a lab 
notebook are legibility and completeness.  When a lab notebook has been written correctly, it should be possible 
for anyone to repeat experiments using ONLY the lab notebook for guidance.  The lab notebook consists of three 
parts:  prelab information, lab record, and post lab discussion/conclusion.  Details can be found in the Course 
Handouts book. 
 
PRELABS: 
 It is extremely important to be organized in order to maximize your learning (and minimize the time spent) in this 
class.  In order to facilitate this, a prelab will be required each week at the beginning of the laboratory period.  You 
will not be allowed to perform the lab or take the prelab quiz until after the prelab has been checked and initialed 
by your instructor.  Unless otherwise specified, you will be asked to perform the lab using only your lab notebook.  
Therefore, it will be vitally important to write an organized, complete prelab.   
 
PRE LAB QUIZZES: 
There will be a quiz given during the first five minutes of each lab period.  You may use your lab notebook (and 
only your lab notebook) on the prelab quiz.  There will be NO make-up for any missed quizzes (including those 
missed due to tardiness).   
 
LAB RECORD: 
The lab record will be checked and initialed by your instructor at the end of each lab period. 
 
LAB REPORTS: 
 Each lab report will consist of the Results, Discussion, & Conclusion sections in your lab notebook.  Guidelines for 
what you should include can be found at the end of each lab in the Course Handouts book.  The report will be due 
on the Monday after the lab was finished, unless otherwise indicated by your instructor.  No late lab reports will 
be accepted!   
 
PROJECT: 
There will be one project required during the semester.  The project will consist of multiple parts and will include 
both research and writing components.  The projects may include both individual and group assignments.  Further 
information on the specific details of the project will be provided in Cobra Learning. 
 
EXAMS: 
Justin E Culbertson  Chemistry 204 
syllabus_S15.docx - 3 - January 8, 2015 
Two (2) written exams will be given to assess your understanding of the theories and principles behind the 
application of organic chemistry in the laboratory.  These exams will focus on both the content of the labs and the 
skills learned during the labs.  These exams will be hour exams and the first will be given during the lecture time 
slot as shown on the course schedule.  The second will be given during final exam time slot, as shown on the 
course schedule. 
 
LAB PRACTICAL: 
 There will be a lab practical given during the lab time slot as shown on the course schedule.  Details on what the 
practical will consist of will be provided.  Failure to take the lab practical will result in an F for the course. 
 
GRADING: 
 
Category Points  Letter grade Range 
Introduction Assignments 4  
A 900 - 1000 
Quizzes (prelab) – Best 12 (5 points each) 60  
Attendance (lecture) – Best 11 (3 points each) 33  
B 800 - 899 
Attendance (laboratory) – Best 13 (5 points each) 65  
Pre-Lab – Best 12 (4 points each) 48  
C 700 - 799 
Lab Record – Best 12 (5 points each) 60  
Reports  – Best 10 (33 points each) 330  
D 600 - 699 
Project 100  
Exams 200    
Lab Practical 100    
Total 1000    
     
HELPFUL HINTS: 
While organic chemistry has the reputation of being a difficult course, I fully expect that everyone should 
successfully complete this course.  If you are experiencing difficulty with the material, please get help as soon as 
possible.  Help can be found during my office hours, by emailing questions to me, by visiting the Center for 
Academic Success, and by talking to your classmates.  The Writing Center is available if help is needed for the 
writing portions of this class.  Please do not be shy about getting help as soon as you realize you need it.  
 
I can help make learning easier, but I can’t learn the material for you. You need to make sure you come to class, 
read the manual(s), do the assignments, ask questions, and keep up with deadlines. 
 
If you believe you have a disability for which you may need an academic accommodation (e.g. an alternate testing 
environment, use of assistive technology or other classroom assistance), please contact: Cathy Robinson, Room 
X148, 217-353-2082, crobinson@parkland.edu 
 
ACADEMIC HONESTY: 
You are expected to complete all your quizzes/exams alone without receiving or giving outside assistance - Your 
brain does your quiz/exam. Academic dishonesty (cheating) is grounds for failure of this 
course and academic discipline. Unethical conduct during examinations or in preparation of assignments 
is unacceptable and may result in disciplinary action. If you use outside resources on any written 
assignment, you need to remember to cite all work that is not your own in order to avoid plagiarism. 
 
PARKLAND POLICIES & SERVICES: 
See the syllabus addendum for more complete information on Parkland Policies & Services. 
  
Justin E Culbertson  Chemistry 204 
syllabus_S15.docx - 4 - January 8, 2015 
TENTATIVE SCHEDULE – SPRING 2015 
 
Week Lecture  (Monday) Lab (Wednesday) Lecture Readings 
1 Introduction / Melting Points  
Safety 
Lab Notebook / Lab Policies 
Hansen 1-2;  
Sonnichsen: 2-18, 23 
Zubrick 1-37, 87-93 
2 
Martin Luther King Day  
 No Class 
Check-In / Melting Points & 
Recrystallization (Parts A & B)  
 Hansen: 1-2; 7-12, 19-24;  
Sonnichsen: 22-25  
Zubrick: 38-49, 104-119 
3 Recrystalization 
Melting Points & 
Recrystallization (Part C) 
 
4 Extraction / Rotary Evaporation Separation by Extraction 
Hansen: 19-28 
Sonnichsen: 26-27 
Zubrick: 80-83, 127-140, 195-
199, 342-344 
5 
Chromatography (TLC & 
Column) 
Thin Layer Chromatography 
Sonnichsen: 28-40 
Zubrick: 218-241 
6 Chromatography (Column) 
Column Chromatography  
 
Hansen: 41-45 
Sonnichsen: 36-40 
Zubrick: 234-241 
7 
Extraction Review / Sublimation 
/ Gas Chromatography 
Isolation of Caffeine from Tea 
Hansen: 19-24 
Sonnichsen: 41-46  
Zubrick: 211-213, 348-357 
8 Exam I  
Isolation of Caffeine from Tea 
(continued) 
 
9 Distillation 
Distillation & Gas 
Chromatography 
Hansen: 33-48  
Sonnichsen: 47-48 
Zubrick: 146-151, 154-170, 178-
183, 324-339 
10 IR Spectroscopy IR Spectroscopy 
Hansen: 79-81 
Sonnichsen: 19, 51-53 
Zubrick: 268-283, 294-300 
Spring Break – March 22 – Marh 28 – No Class 
11 Bromine Addition / Reflux 
Bromine Addition to trans-
Cinnamic Acid 
Hansen: 167-170 
Sonnichsen: 54-55 
Zubrick: 200-202 
12 SN1 Substitution SN1 Substitution 
Hansen: 141-147 
Sonnichsen: 57 
13 
Elimination / Heterogenous 
(Steam) Distillation 
Dehydration of Cyclohexanol 
Hansen: 109-112 
Sonnichsen: 56 
Zubrick: 183-187, 339-341 
14 Chlorination Chlorination of Heptane  
Hansen: 99-104 
Sonnichsen: 58 
15 Project  Project Day   
16 Technique Review Lab Practical  
Exam II  
Section 002 (PM) 
Monday, May 11 
6:00 – 8:00 PM 
 
 


Chemistry 201 Organic Chemistry I Laboratory Spring 2015

Scholarship at Parkland

Parkland CollegeChemistry Courses Natural Sciences Courses2015Chemistry 201 Organic Chemistry I LaboratorySpring 2015Justin CulbertsonParkland College, jculbertson@parkland.eduOpen access to this Course Materials is brought to you by Parkland College's institutional repository, SPARK: Scholarship at Parkland. For moreinformation, please contact spark@parkland.edu.Recommended CitationCulbertson, Justin, "Chemistry 201 Organic Chemistry I Laboratory Spring 2015" (2015). Chemistry Courses. Paper 36.http://spark.parkland.edu/chem_course/36Justin E Culbertson  Chemistry 204 syllabus_S15.docx - 1 - January 8, 2015  SPRING 2015 – CHE 204 ORGANIC CHEMISTRY I LABORATORY  INSTRUCTOR:   Justin E. Culbertson  CONTACT INFORMATION: Office:  L 262     Phone:  (406) 836-7981     Text: (406) 836-7981     Email:  jeculbe2@illinois.edu      OFFICE HOURS:  In L262:  M 7:00 – 8:00 PM I’m also available by appointment.  LECTURE:      Section 002: M 6:00 – 6:50 PM in L216      LABORATORY:  Section 002: W 6:00 – 9:00 PM in M228  REQUIRED MATERIALS: Experiments for Organic Chemistry I, Illinois State University lab manual  Labs, Lab Reports, & Course Handouts, Parkland College lab manual  Duplicate page laboratory notebook and an ink pen  Lab safety goggles (glasses are NOT acceptable)  iClicker  OPTIONAL MATERIALS: Organic Chem Lab Survival Manual, J. W. Zubrick, 9th edition   COURSE SCHEDULE:  The course schedule is available in Cobra Learning, where it will be updated as needed.  COURSE DESCRIPTION:  Chemistry 204, Organic Chemistry I Laboratory, is a beginning organic chemistry laboratory course that teaches basic laboratory techniques (recrystallization, melting point, TLC, column chromatography, GC, refluxing, distillation, spectroscopy, etc.) and provides experience in performing simple organic reactions.  PREREQUISITES:  Parkland College CHE 101 and CHE 102 or equivalent with a grade of C or higher and concurrent enrollment in CHE 203.  GOALS:  Foundation – Know basic terms. Understand writing skills and experimental techniques required in an advanced organic chemistry lab.  Apply – Apply writing and experimental skills. Analyze and discuss experimental results. Manage small and large laboratory projects effectively.  Integrate – Connect information within this course, with the organic lecture courses, and with your life experiences.  YOUR Growth – Feel increasingly comfortable in a chemistry lab, working with a team of others. Increase interest in scientific experiments and/or applications. Reflect on and understand how you learn best in a chemistry lab course.  ATTENDANCE:  Attendance at both the lecture and the lab sessions will be graded.  Lecture attendance will be based on your participation in clicker questions throughout the lecture period.  These questions will be graded on a completion basis only.  If you participate in all clicker questions during a lecture period, you will receive your full lecture attendance score.   In order to successfully complete this class you MUST attend all labs.  In order for an absence to count as excused, you must provide a documented excuse for your absence (religious holiday, medical appointment, Justin E Culbertson  Chemistry 204 syllabus_S15.docx - 2 - January 8, 2015 approved college athletic activity or death in the immediate family).  If you are sick enough to miss lab then you are sick enough to go and see a doctor!  If at all possible, inform your instructor of any anticipated absences PRIOR to the absence.  Anyone who does not follow the lab rules provided, including additional rules as stated by your instructor, may be asked to leave the laboratory.  If you are asked to leave lab, the lab will be counted as an unexcused absence.  In addition, lab penalties may be taken out of your lab attendance grade.  A list of penalties can be found on the Organic Chemistry Lab Rules handout.  Additional penalties may be determined on a lab by lab basis.  All penalties will be clearly stated before being applied.   Unlike other classes, most organic chemistry labs take three (3) hours to complete.  Therefore, you should never expect to leave lab early.  Also, anyone arriving late to lab will experience difficulty finishing his or her lab during the allotted time slot.  It is very important that you come to lab on time and ready to work.  Lab begins precisely at the time listed on the clock in the laboratory.  At the beginning of lab demonstrations and safety instructions are made.  Arriving even one minute late means that you missed part of this and your lab participation grade will be negatively affected.  If you arrive after the safety announcements you may not start the lab and it is considered an unexcused absence.    There will be NO make-up labs.  You will receive a 0 for all assignments associated with any missed lab (lab attendance, pre-lab quiz, notebook – both prelab & lab record, and lab report).  Two unexcused absences from lab will result in an automatic F for the course.  LAB NOTEBOOKS: How to keep a laboratory notebook properly is one of the most important skills to be learned in an organic chemistry lab.  During this semester an emphasis will be placed on how well you keep a lab notebook.  Both the structure and the content of the notebook will be evaluated.  An excellent reference for how to keep a lab notebook is The Organic Chem Lab Survival Manual, by J. W. Zubrick.  The most important aspects of a lab notebook are legibility and completeness.  When a lab notebook has been written correctly, it should be possible for anyone to repeat experiments using ONLY the lab notebook for guidance.  The lab notebook consists of three parts:  prelab information, lab record, and post lab discussion/conclusion.  Details can be found in the Course Handouts book.  PRELABS:  It is extremely important to be organized in order to maximize your learning (and minimize the time spent) in this class.  In order to facilitate this, a prelab will be required each week at the beginning of the laboratory period.  You will not be allowed to perform the lab or take the prelab quiz until after the prelab has been checked and initialed by your instructor.  Unless otherwise specified, you will be asked to perform the lab using only your lab notebook.  Therefore, it will be vitally important to write an organized, complete prelab.    PRE LAB QUIZZES: There will be a quiz given during the first five minutes of each lab period.  You may use your lab notebook (and only your lab notebook) on the prelab quiz.  There will be NO make-up for any missed quizzes (including those missed due to tardiness).    LAB RECORD: The lab record will be checked and initialed by your instructor at the end of each lab period.  LAB REPORTS:  Each lab report will consist of the Results, Discussion, & Conclusion sections in your lab notebook.  Guidelines for what you should include can be found at the end of each lab in the Course Handouts book.  The report will be due on the Monday after the lab was finished, unless otherwise indicated by your instructor.  No late lab reports will be accepted!    PROJECT: There will be one project required during the semester.  The project will consist of multiple parts and will include both research and writing components.  The projects may include both individual and group assignments.  Further information on the specific details of the project will be provided in Cobra Learning.  EXAMS: Justin E Culbertson  Chemistry 204 syllabus_S15.docx - 3 - January 8, 2015 Two (2) written exams will be given to assess your understanding of the theories and principles behind the application of organic chemistry in the laboratory.  These exams will focus on both the content of the labs and the skills learned during the labs.  These exams will be hour exams and the first will be given during the lecture time slot as shown on the course schedule.  The second will be given during final exam time slot, as shown on the course schedule.  LAB PRACTICAL:  There will be a lab practical given during the lab time slot as shown on the course schedule.  Details on what the practical will consist of will be provided.  Failure to take the lab practical will result in an F for the course.  GRADING:  Category Points  Letter grade Range Introduction Assignments 4  A 900 - 1000 Quizzes (prelab) – Best 12 (5 points each) 60  Attendance (lecture) – Best 11 (3 points each) 33  B 800 - 899 Attendance (laboratory) – Best 13 (5 points each) 65  Pre-Lab – Best 12 (4 points each) 48  C 700 - 799 Lab Record – Best 12 (5 points each) 60  Reports  – Best 10 (33 points each) 330  D 600 - 699 Project 100  Exams 200    Lab Practical 100    Total 1000         HELPFUL HINTS: While organic chemistry has the reputation of being a difficult course, I fully expect that everyone should successfully complete this course.  If you are experiencing difficulty with the material, please get help as soon as possible.  Help can be found during my office hours, by emailing questions to me, by visiting the Center for Academic Success, and by talking to your classmates.  The Writing Center is available if help is needed for the writing portions of this class.  Please do not be shy about getting help as soon as you realize you need it.   I can help make learning easier, but I can’t learn the material for you. You need to make sure you come to class, read the manual(s), do the assignments, ask questions, and keep up with deadlines.  If you believe you have a disability for which you may need an academic accommodation (e.g. an alternate testing environment, use of assistive technology or other classroom assistance), please contact: Cathy Robinson, Room X148, 217-353-2082, crobinson@parkland.edu  ACADEMIC HONESTY: You are expected to complete all your quizzes/exams alone without receiving or giving outside assistance - Your brain does your quiz/exam. Academic dishonesty (cheating) is grounds for failure of this course and academic discipline. Unethical conduct during examinations or in preparation of assignments is unacceptable and may result in disciplinary action. If you use outside resources on any written assignment, you need to remember to cite all work that is not your own in order to avoid plagiarism.  PARKLAND POLICIES & SERVICES: See the syllabus addendum for more complete information on Parkland Policies & Services.   Justin E Culbertson  Chemistry 204 syllabus_S15.docx - 4 - January 8, 2015 TENTATIVE SCHEDULE – SPRING 2015  Week Lecture  (Monday) Lab (Wednesday) Lecture Readings 1 Introduction / Melting Points  Safety Lab Notebook / Lab Policies Hansen 1-2;  Sonnichsen: 2-18, 23 Zubrick 1-37, 87-93 2 Martin Luther King Day   No Class Check-In / Melting Points & Recrystallization (Parts A & B)   Hansen: 1-2; 7-12, 19-24;  Sonnichsen: 22-25  Zubrick: 38-49, 104-119 3 Recrystalization Melting Points & Recrystallization (Part C)  4 Extraction / Rotary Evaporation Separation by Extraction Hansen: 19-28 Sonnichsen: 26-27 Zubrick: 80-83, 127-140, 195-199, 342-344 5 Chromatography (TLC & Column) Thin Layer Chromatography Sonnichsen: 28-40 Zubrick: 218-241 6 Chromatography (Column) Column Chromatography   Hansen: 41-45 Sonnichsen: 36-40 Zubrick: 234-241 7 Extraction Review / Sublimation / Gas Chromatography Isolation of Caffeine from Tea Hansen: 19-24 Sonnichsen: 41-46  Zubrick: 211-213, 348-357 8 Exam I  Isolation of Caffeine from Tea (continued)  9 Distillation Distillation & Gas Chromatography Hansen: 33-48  Sonnichsen: 47-48 Zubrick: 146-151, 154-170, 178-183, 324-339 10 IR Spectroscopy IR Spectroscopy Hansen: 79-81 Sonnichsen: 19, 51-53 Zubrick: 268-283, 294-300 Spring Break – March 22 – Marh 28 – No Class 11 Bromine Addition / Reflux Bromine Addition to trans-Cinnamic Acid Hansen: 167-170 Sonnichsen: 54-55 Zubrick: 200-202 12 SN1 Substitution SN1 Substitution Hansen: 141-147 Sonnichsen: 57 13 Elimination / Heterogenous (Steam) Distillation Dehydration of Cyclohexanol Hansen: 109-112 Sonnichsen: 56 Zubrick: 183-187, 339-341 14 Chlorination Chlorination of Heptane  Hansen: 99-104 Sonnichsen: 58 15 Project  Project Day   16 Technique Review Lab Practical  Exam II  Section 002 (PM) Monday, May 11 6:00 – 8:00 PM   

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Chemistry 201 Organic Chemistry I Laboratory Spring 2015

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