QUEENSBOROUGH COMMUNITY COLLEGE
CHEMISTRY DEPARTMENT
COURSE SYLLABUS
CH-128: INTRODUCTORY ORGANIC CHEMISTRY
Pre-Requisite
CH-120, CH-127 or CH-151
Hours
3 Lecture Hours
Textbook
Introduction to Organic and Biochemistry, Custom Edition, ISBN-13:
978-1-305-31493-1 by Bettelheim, Brown, Campbell, and Farrell
(Cengage Learning). Customized from ‘Introduction to General,
Organic and Biochemistry’, 10th Edition, ISBN-13: 978-1-133-10508-4
by Bettelheim, Brown, Campbell, Farrell, and Torres.
Lab manual
Organic Chemistry Laboratory Manual, 2nd Ed, ISBN-0-697-33923-8
by P. Svoronos, E. Sarlo and R. J. Kulawiec (WCB McGraw-Hill)
4 Laboratory Hours
4 ½ Credits
Course Description
This course is the second of a two-semester sequence and is intended to provide a
brief, but thorough introduction to organic chemistry and biochemistry. The major
functional groups such as hydrocarbons, alcohols, ethers, amines, carbonyl compounds
and their derivatives are studied with some emphasis on nomenclature, reactions, and
stereochemistry. Several aspects of organic chemistry related to biochemistry are also
stressed including units on amino acids, proteins, enzymes, carbohydrates and lipids.
The laboratory introduces students to the various synthetic methods for making organic
compounds, as well as to purification techniques like distillation, recrystallization and
extraction.
Curricula for Which the Course is Required/Recommended
This course is recommended for students in Nursing and others planning to pursue
careers in the Allied Health fields. It may be used as a preparation for CH-251, but may
not be substituted for CH-251 and is not open to students who have already completed
CH-251 or CH-252.
General Education Objectives
The general education objectives are to: a) communicate effectively through reading,
writing, listening and speaking, b) use analytical reasoning to identify issues or
problems and evaluate evidence in order to make informed decisions, c) integrate
knowledge and skills in their program of study, d) work collaboratively in diverse groups
directed at accomplishing learning objectives, and e) employ concepts and methods of
the natural and physical sciences to make informed judgments.
Spring 2016
CH-128 SYLLABUS
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Course Objectives/Expected Student Learning Outcomes
Understand the nomenclature, structures and reactions of simple organic compounds:
alkanes, alkenes, alkynes, alcohols, amines, aldehydes, ketones, amides, esters,
carboxylic acids and their derivatives. Attain knowledge of basic concepts of
biomolecules such as amino acids, proteins, enzymes, carbohydrates and lipids.
Correlate structures and reactivity of simple organic compounds and develop scientific
research abilities such as planning and performing experiments, gathering and
analyzing data, drawing conclusions from qualitative analysis, communicating results
orally and in scientific writing and demonstrating some familiarity with chemical literature.
Methods by Which Student Learning Will Be Evaluated
The general guidelines for assessing grades are as follows:
 Examinations, Assignments and Classroom Performance
 Laboratory Work
 Final Examination
50%
25%
25%
The distribution may be changed at the discretion of the individual instructor. Aside from
the above guidelines, the students are mandated to take the American Chemical
Society (ACS) assessment test which is administered during the 14th week of the
laboratory period (see Laboratory Schedule) and 10% of that grade will be added on top
of the student’s final course grade. The ACS test cannot hurt your grade.
Attendance/Absence Policy for Lecture
Attendance will be taken at every class. The Student Handbook states that you will be
considered excessively absent from a course and will receive a WU grade if you have
been absent for 15% or more of the total number of contact hours for your course. If
there is a laboratory component to your course, you will be considered excessively
absent if you miss 15% or more of either component. A WU is computed as an F in
your GPA. Students who have valid excuses for missed classes should speak with their
instructor and present documentation explaining the reason for the absence. Absences
that have been excused by the instructor will not be counted toward a WU grade.

If your class meets twice per week: you will receive a grade of WU if
you have a total of 6 or more excused and/or unexcused absences.

For any lecture that meets only once per week, you will receive a grade
of WU if you have a total of 3 or more excused and/or unexcused
absences.
Accommodations for Students with Disabilities
Any student who feels that he/she may need an accommodation based upon the impact
of a disability should contact the office of Services for Students with Disabilities in
Science Building, room 132 (718-631-6257) to discuss his/her specific needs and to
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coordinate reasonable accommodations for documented disabilities. Students should
also contact their instructor privately to discuss their specific needs.
Academic Integrity
Academic honesty is taken extremely seriously and is expected of all students. All
assignments must be the original work of the student (and partners or group, if
applicable). All questions or concerns regarding ethical conduct should be brought to
the course instructor. “It is the official policy of the College that all acts or attempted acts
that are violations of academic integrity be reported to the Office of Student Affairs
(OSA). At the faculty member’s discretion and with the concurrence of the student or
students involved, some cases, though reported to the OSA, may be resolved within the
confines of the course and department. The instructor has the authority to adjust the
offender’s grades as deemed appropriate, including assigning an F to the assignment or
exercise or, in more serious cases, an F to the student for the entire course.” (Taken
from the QCC Academic Integrity Policy, 2/14/2005.)
Laboratory Policy
All lab policies will be explained in detail by your lab instructor.
Three (3) or more absences from the lab earn a grade of WU in the lab. For CH127/128, CH-151/152, CH-251/252, a WU in the lab results in a WU for the entire
course. The first and last lab meetings are mandatory and count against your total
attendance.
There are no make-up sessions for missed labs. Policies regarding excused and
unexcused absences will be explained by your lab instructor. A full lab report is required
for each experiment and is due the next class period. Your lab instructor will describe
the format for lab reports, as well as requirements for entry into the lab. Students who
arrive after the pre-lab lecture may not participate and will be marked absent.
Safety in the lab is extremely important. Therefore, the ACS safety video must be
viewed during the first lab session. A safety quiz must be taken and passed, and the
safety declaration sheet must be signed. A student that shows up for the lab, but who
has not seen the safety video and passed the quiz, will not be permitted to conduct the
experiment, will be considered absent, and will receive a zero for the lab. There will be
several additional showings of the safety video during the first three weeks of classes. A
student who has not viewed the safety video and passed the quiz by the third lab
session will have accumulated 3 absences in the lab and therefore will not be
permitted to continue in the course. They may either withdraw or receive a WU for
the course.
Required attire: Students MUST wear safety goggles in the lab at all times. Shorts and
short skirts, tank tops and cropped tops, sandals and open-toed shoes, untied long hair,
and any type of food or beverage in the lab are forbidden. Students who fail to follow
these rules will not be permitted to perform the experiment. They will be marked absent
and will be given a zero that lab.
CH-128 SYLLABUS
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CH-128: INTRODUCTORY ORGANIC CHEMISTRY
LECTURE SCHEDULE
CHAPTER
TOPIC
HOURS
1 (10)
Organic Chemistry
1
2 (11)
Alkanes
4
3 (12)
Alkenes and Alkynes
3
4 (13)
Benzene and Its Derivatives
2
5 (14)
Alcohols, Ethers, and Thiols
3
6 (15)
Chirality: The Handedness of Molecules
3
7 (16)
Amines
3
8 (17)
Aldehydes and Ketones
3
9 (18)
Carboxylic Acids
3
10 (19)
Carboxylic Anhydrides, Esters, and Amides
3
13 (22)
Proteins
3
14 (23)
Enzymes
3
11 (20)
Carbohydrates
3
12 (21)
Lipids
2
Exams
6
NOTE:
1. The approximate hours per chapter are guidelines and are at the discretion of the
instructor. The instructor is responsible for making assignments and scheduling
examinations. The Final Exam date is scheduled by the Registrar.
2. Numbers in the parenthesis under ‘Chapter’ indicate the chapters in the 10th edition
textbook.
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Lab Report Format
The pre-lab report (#1 - 5, up to “Experimental Procedure” section) must be completed
before coming to lab and the final report (#1-9) should be completed and submitted by
the next lab period.
Prelab Report
1. Your Name and Partner’s Name
2. Title: The title of the experiment. The title should be simple and specific.
e.g. Synthesis of Cyclohexene (not “Synthesis of Alkene” because there are many
different alkenes)
3. Objective: (1-2 sentences) Why do you do this experiment? What is the goal of this
experiment? e.g. “to separate benzoic acid and p-dichlorobenzene from the mixture
using the solvent extraction technique”
* Do not mention the procedure or the background information here.
4. List of Materials and Equipments: Include important properties of all chemicals
(molecular weight, boiling and melting points, density, etc.). Do not include standard
laboratory reagents. The only time the reaction apparatus is discussed in the section
is when the apparatus is not a standard apparatus. Please keep in mind that
beakers, Erlenmeyer flasks, funnels, graduate cylinder, test tubes, etc. are all
standard laboratory glassware and they do not need to be mentioned.
5. Experimental Procedure: You will need to write an accurate procedure that will
permit you to complete the experiment. Use numbers or bullets for each step, and
make each step simple. The purpose for having the flowchart in lab is to ensure that
you have read over the procedure ahead of time. It is not safe to begin lab work
without the adequate preparation. The experimental procedure should be written on
the left half of the page, leaving the right half for the observations section.
(Example)
5. Procedure
6. Observations
(1) cyclohexanol (10g) is added to a 50mL
round bottom flask.
(2) Na2Cr2O7 (10g) is dissolved in 10 mL
water in a 125mL Erlenmeyer flask.
(3) …………..
(4) ……………………
(5) …….
(6) do simple distillation……………..
(7) determine the bp and calculate the %yield
* Instructor’s Signature _________________________
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Post lab Report:
6. Observations: Write down anything you observed (color change, formation of
bubble, weight of compound used and/ or obtained, m.p., b.p., etc). What you write
here will be used for the “Results” and/or “Discussion” sections.
(Example)
5. Procedure
6. Observations
(1) cyclohexanol (10g) is added to a 50mL
round bottom flask.
(2) Na2Cr2O7 (10g) is dissolved in 10 mL
water in a 125mL Erlenmeyer flask.
(3) …………..
(4) …….
(5) ………
(6) do simple distillation……………..
(7) determine the bp and calculate the %yield
9.934g cyclohexanol added
10.1 g Na2Cr2O7 added
color changed from orange to
brown
The distillate was collected
between 90-100°C, total about
8mL
b.p. = 98°C,
7.
Results: Summarize your results here. Record the amount of reactants and
products, the appearance of your product, the melting point or boiling point, the
percent yield, graph, etc. Describe how you calculated the results using the proper
units. Although you write your data and results in “Observations” section, you have
to re-write them here using complete sentences.
8.
Discussion/Conclusion: The experimental results are always discussed in this
section. Describe if and how the experimental objectives were met. If tests were
performed to confirm the product, describe how you made your decision from the
test results. If you have unexpected results such as low or high % yield, etc., explain
and justify the results.
9. Questions: Answer the post laboratory questions assigned in the laboratory manual.
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CH-128: INTRODUCTORY ORGANIC CHEMISTRY
LABORATORY SCHEDULE
WEEK
TOPIC
EXPERIMENT
PAGES
1
Check-in; Introductory Remarks
Laboratory Safety & Equipment; The Basics
1
1- 4
2
Distillation - Simple & Fractional (p 33, #1, 2)
4.1 & 4.2
29 – 32*
3**
Recrystallization of a Solid (p 71, #1, 2)
6.3
66 – 70
4
Separation by Extraction (p 65, #1)
6.2
63 – 65
5
Dehydration of tert-Amyl Alcohol
6
Synthesis of t-Butyl Chloride (p 153, #1)
13.1
151 – 152*
7
Qualitative Tests for Alcohols (p 182, #2 and
draw all the alcohols on p. 183)
14.2
180 – 182*
8
Oxidation of Cyclohexanol to Cyclohexanone
(p 225, #1, 3, and a quiz on percent yield)
17.1
223 – 225*
9
Equivalent Weight of Organic Acids (p 205, #1a, 3) 16.1
204 – 205
10
Synthesis of Aspirin (p 215, #4)
16.3
214 – 215
11
Synthesis of Acetanilide (p 257, #1)
19.2
255 – 256
12
Preparation of Phenacetin (p 186-7, #1, 3, 6)
14.3
185 – 186*
13
Lipids – Preparation and Properties of a Soap
& The Hanus Test (p. 307, #1, 2, 3)
23.1
23.2
305 – 307*
311 – 312*
14
ACS Assessment Test
15
Check-out
handout***
NOTE: Questions to be answered in the lab report are in parentheses.
*
designates labs that have modifications to their procedures. See the next page titled
‘Modifications to the Laboratory Procedures’
** If the Safety Video has not been seen before this experiment, you will not be
allowed to continue in the course!
*** handout for the complete lab is attached at the end of this syllabus
CH-128 SYLLABUS
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MODIFICATIONS TO THE LABORATORY PROCEDURES
EXPERIMENT TITLE
DESCRIPTION OF THE MODIFICATION
Distillation – Simple & Fractional
For Part II, step 2 (p 31) of the simple distillation,
collect only 10 mL of distillate. Do the same for the
fractional distillation (step 2, p 32).
Synthesis of t-Butyl Chloride
For step 1 (p 152), do not heat past 55-60 °C. For
step 5, substitute sodium sulfate for magnesium
sulfate. For step 6, just decant the liquid instead of
using a gravity filter and do not perform the simple
distillation. For step 7, please check with your
instructor first.
Qualitative Tests for Alcohols
For the Jones’ oxidation (p 180), warm test tubes
only if the color does not change. For the Lucas
reaction, heat only if the test tubes are not cloudy
after 5 minutes. For the Iodoform test, use only 5
drops of both the positive test sample and the
unknown and perform each test in a beaker since
larger quantities of KI/I2 are needed.
Oxidation of Cyclohexanol
For step 9 (p 225), use sodium sulfate instead of
magnesium sulfate. For step 10, decant the liquid
instead of gravity filter and do not perform a
distillation. Instead, weigh the liquid and calculate
the percent yield. For steps 11 and 12, check with
your instructor first.
Preparation of Phenacetin
For step 2 (p 186), 0.50 g of iodoethane should be
changed to 1.95 g). For step 6, use ethyl acetate
instead of ether. For step 8, use sodium sulfate
instead of magnesium sulfate and decant in step 9
instead of gravity filter. For step 10, use only 4-8 mL
of hot water instead of 10-15 mL. For steps 15 and
16, please check with your instructor first.
Preparation & Properties of Soap
and the Hanus Test
For step 1 (p 307) use coconut oil instead of cotton−
seed oil. For steps 4-8, use a bar soap to make the
soap solution since the soap in step 1 does not
provide enough suds. For the Hanus test, for step 1
(p 312), use 5 drops of each oil instead of 10. Then
check with your instructor as to whether you will do
either step 2 or step 3 (only one is needed).
CH-128 SYLLABUS
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DEHYDRATION OF TERT-AMYL ALCOHOL (2-METHYL-2-BUTANOL) – WEEK 5
H2O
2-methyl-2-butene
H2SO4
OH
2-methyl-2-butanol
Procedure
OH2
+
+
2-methyl-1-butene
1. Setup a simple distillation using a 100 mL round bottom flask as the reaction flask
and a 25 mL round bottom flask as the receiving flask. Keep the receiving flask in an ice
bath to reduce evaporation.
2. Place 10 mL of water into the reaction flask and cool in an ice bath for several
minutes.
3. Use a funnel to transfer 6 mL of concentrated sulfuric acid into a 10 mL graduated
cylinder (note: sulfuric acid is corrosive!).
4. Use a pipette to transfer the concentrated sulfuric acid dropwise to the flask (from
step 2) while continuously swirling.
5. Slowly add 10.0 mL (8.1 g, d= 0.81 g/mL) of tert-amyl alcohol to the flask using a
pipette.
6. Add several boiling chips and then heat the contents. Collect the distillate that boils at
30-43 °C in a receiving flask (25 mL round bottom flask). Continue to collect as long as
the distillate is still flowing into the flask at temperatures above 43°C, but stop the
distillation if it goes above 50 °C.
7. Discontinue heating and transfer the distillate to a separatory funnel (using a funnel).
8. Place 10 mL of 10% NaOH into the separatory funnel and swirl cautiously (release
the vapor immediately).
9. Separate the bottom aqueous layer and place in the designated waste container.
10. Transfer the top organic layer into a small conical flask, dry the organic layer with
approximately 1 g of anhydrous sodium sulfate, and then cover the flask with a watch
glass to prevent evaporation.
11. Use a funnel to carefully decant the liquid from step 10 into a round bottom flask and
set up a simple distillation (avoid the transfer of any crystals of the sodium sulfate into
the distillation set up as they contain water which should be removed).
12. Collect the distillate in a pre-weighed dry vial that is kept in an ice bath to reduce
evaporation. The bp range of the mixture should be 30-43 °C.
13. Calculate the % yield of the mixture of alkene isomers.
14. Add 5-10 drops of the distillate into 5 drops of 1% KMnO 4 in a test tube. Record your
observations. Add 5-10 drops of the distillate into 5 drops of 1% Br 2/H2O in a separate
test tube. Record your observations.
CH-128 SYLLABUS
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Questions
1) Write the reactions that represent the addition of KMnO 4 and Br2 to the two alkenes
that were formed during the reaction. (for assistance in answering the question, refer
to p 123-125 in the laboratory manual which uses cyclohexanol instead of tert-amyl
alcohol)
2) Explain the purpose of the following in the above experiment:
a. Sulfuric acid
b. Simple distillation – in step 1
c. Sodium hydroxide extraction
d. Anhydrous sodium sulfate
e. Ice-cooled receiving/collecting flask
f. Covering the flask with a watch glass in step 10
3) Give all possible alkenes formed during the dehydration of each of the following
alcohols:
a. 1-methylcyclohexanol
b. 2-methylcyclohexanol
c. cyclopentylmethanol
d. 3,3-dimethyl-1-butanol