use as a guide Cuny QCC

1. Spring 2013
COURSE SYLLABUS
CH-251: ORGANIC CHEMISTRY I
Hours: 3 Class Hours 4 Laboratory Hours 1 Recitation Hour 5 Credits
Pre-requisites: CH-151 and CH-152
Course Description: The relationship between structure and properties of organic
compounds are discussed, with emphasis on reaction mechanisms, stereochemistry,
and synthesis. Laboratory work involves preparation, isolation, and identification of
organic compounds.
Curricula for which the course is required/recommended: A.S. Degree Programs in
Liberal Arts and Sciences (Science and Mathematics), Engineering Science, Health
Sciences including Medical Laboratory Technician and those interested in careers in the
Medical, Dental, Veterinary, Pharmacy, Chiropractic, and Physician fields, Forensics,
Pharmaceutical Sciences, and Environmental Health.
General Education Objectives: Use analytical reasoning and mathematical skills to
solve problems; integrate knowledge and skills in their major field and across
disciplines; use information management skills effectively for academic research and
lifelong learning.
Course Objectives/ Expected Student Learning Outcomes: The objective of this
course is to gradually and logically develop the relationship between properties and
structure of organic compounds. The lecture will begin by introducing general chemistry
concepts as they pertain to organic chemistry and will then describe drawing organic
molecules, functional groups, energetics of reactions, and stereochemistry. After the
basics are taught, students will learn reactions of specific functional groups and the
mechanism of the reactions. At the end of the semester, students should be able to
perform multi-step syntheses and be able to work backwards starting from a complex
molecule. In the laboratory, the student will be introduced to the basic techniques
involved in the preparation, isolation, and identification of organic compounds.
Texts: ORGANIC CHEMISTRY, 8TH
ED., L. G. Wade, Pearson Education Inc., ISBN-
13#: 978-0-321-76841-8
WORKBOOK PROBLEMS FOR ORGANIC CHEMISTRY, Sarlo & Svoronos,
Wm. C. Brown Publishers, ISBN-13#: 978-0-07-289968-9
Lab: ORGANIC CHEMISTRY LABORATORY MANUAL, 2ND
ED., P. Svoronos, E.
Sarlo, R. J. Kulawiec, Wm C. Brown Publishers, ISBN-13#: 978-0-697-33923-2
QUEENSBOROUGH COMMUNITY COLLEGE which is
easier at queens college
CHEMISTRY DEPARTMENT
Use this as a guide for your next class This class is usally the same all around

2. Spring 2013
CH-251: ORGANIC CHEMISTRY I
Methods by which student learning will be evaluated: The general guidelines for
assessing grades are as follows:
o Examinations, Assignments and Classroom Performance 50%
o Laboratory Work 25%
o Final Examination 25%
The distribution may be changed at the discretion of the individual instructor. Aside from
the above, the student is mandated to take the American Chemical Society (ACS)
assessment test which will be administered at the end of the semester. Ten percent of
that grade will be added, as a bonus, to the student’s final course grade.
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 the Science Building, Room S-132
(718-631-6257) to discuss his/her specific needs and to 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.)
Attendance/Absence Lecture Policy: 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. 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 at the discretion of the instructor will not be counted toward a WU grade.

3. Spring 2013
CH-251: ORGANIC CHEMISTRY I
 If your class meets twice per week: you will receive a grade of WU if
you have a total of 6 or more unexcused absences.
 If your class meets once per week: you will receive a grade of WU if you
have a total of 3 or more unexcused absences.
 If your class meets 3 or 4 times a week (summer session): you will
receive a grade of WU if you have a total of total of 2 or more unexcused
absences.
Laboratory Policies
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. A WU in
the lab results in a WU for the entire course. The first and last lab meetings are also
mandatory and will count against your total attendance. Policies regarding excused and
unexcused absences will be explained by your lab instructor.
There are no make-up sessions for missed labs. 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 two 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 for that lab.

4. Spring 2013
CH-251: ORGANIC CHEMISTRY I
LECTURE SCHEDULE
CHAPTER TOPIC HOURS*
1 Introduction and Review 3
2 Structure and Properties of Organic Molecules 3
3 Structure and Stereochemistry of Alkanes 5
4 The Study of Chemical Reactions 4
5 Stereochemistry 5
6 Alkyl Halides: Nucleophilic Substitution 6
and Elimination
7 Structure and Synthesis of Alkenes 5
8 Reactions of Alkenes 5
9 Alkynes 3
10 Structure and Synthesis of Alcohols 4
11 Reactions of Alcohols 3
14 Ethers, Epoxides, and Sulfides 4
* 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.

5. Spring 2013
CH-251: ORGANIC CHEMISTRY I: LABORATORY SCHEDULE
LAB EXPERIMENT TITLE EXPT. # Page#
1 Check-in; Lab Techniques; Safety Video --- ---
2 Melting Points* 3.1 21
4 Steam Distillation* 4.3 38
5 Separation by Extraction 6.2 64
Recrystallization of a Solid 6.3 69
6 Distribution coefficient --- handout**
7 Equilibrium Constant* 7 80
8 Dehydration of tert-Amyl Alcohol --- handout**
9 Synthesis of tert-Butyl Chloride* 13.1 152
10 The Pinacol Rearrangement* 17.4 232
11 Solvolysis of t-Butyl Chloride: 13.2 156
A Kinetic Study
12 The Grignard Reaction (Part 1) 14.1 175
13 The Grignard Reaction (Part 2) 14.1 175
14 ACS Exam
15 Checkout
* designates labs that have modifications to their procedures. See the next page titled
‘Modifications to the Laboratory Procedures’
** handouts are at the end of the syllabus
3 Distillation - Simple and Fractional 4.1 & 4.2 31, 32

6. Spring 2013
MODIFICATIONS TO THE LABORATORY PROCEDURES
EXPERIMENT TITLE DESCRIPTION OF THE MODIFICATION
Melting Points Do Part B only but you will need to refer to
steps 4, 5, and 6 from Part A (p. 21) to do the
experiment.
Steam Distillation For step 6 (p. 38), gravity filter into a pre-
weighed, small beaker and remove the organic
solvent (CH2Cl2) under the hood using a hot
water bath.
Equilibrium Constant Use half the quantity for each reagent (p. 80):
therefore, acetic acid (7.2 mL) and n-propanol
(9.4 mL) and switch to using a 50 mL round
bottom (instead of 100 mL) flask.
Synthesis of t-Butyl Chloride For step 7 (p. 152), please check with your
instructor first.
The Pinacol Rearrangement For step 7 (p. 233), please check with your
instructor first regarding the IR. Do the same
for step 8 regarding the NMR.
,

7. Spring 2013
DISTRIBUTION COEFFICIENT – LAB 6
The experimental procedure is modified slightly from the one in the lab manual (p.
56). Please read the lab manual first to understand the background information and
important equations used during the experiment (p. 54-55).
Procedure
1. Place 1 mL of acetic acid into a 125 mL Erlenmeyer flask. Then add 59 mL of water.
Therefore, the total solution volume is 60 mL.
2. Take a 10 mL aliquot of the acid solution using a pipette and transfer it to a second
Erlenmeyer flask. Add 2 drops of phenolphthalein indicator and then titrate with a 0.2
N NaOH solution to a pale pink endpoint.
3. Take another 10 mL aliquot of the acid solution from step 1 and transfer it to a
separatory funnel. Extract with 10 mL of ethyl acetate.
4. Drain the bottom, aqueous layer into an Erlenmeyer flask, add 2 drops of the
indicator, and titrate as before.
5. Take a third 10 mL aliquot of the acid solution and transfer it to a separatory funnel
but now extract it twice, each time with 5 mL of ethyl acetate.
6. Drain the bottom, aqueous layer into an Erlenmeyer flask, add 2 drops of the
indicator, and titrate as before.
7. Now repeat steps 3-6 but using toluene instead of ethyl acetate. Therefore the
efficiency of extraction of ethyl acetate versus toluene can be tested.
8. In the end, a total of five titrations will have been performed. This will leave behind
~10 mL of the acid solution from step 1.
9. To clean the burette (while still attached to the clamp), drain all the liquid. Then add
10 mL of water and drain. Then add 10 mL of dilute hydrochloric acid and drain.
Then finally add 50 mL of water, in portions, and drain. Do not unclamp the burette
until all draining and washing is completed.
Questions
1) Based on your data, is acetic acid more soluble in water or ethyl acetate? How about
water versus toluene?
2) Which of the following organic solvents can be used in this experiment: ethanol,
acetone, diethyl ether, methylene chloride, propanoic acid, acetonitrile? Explain your
answer (Hint: Look up the water solubilities of each compound in a reference book
before answering this question [e.g., the CRC Handbook of Chemistry and Physics
or use this lab manual, Table 6.1])
3) Compared to acetic acid, is hexanoic acid (CH3(CH2)4COOH) more or less soluble in
water? Explain.

8. Spring 2013
DATA SHEET: DISTRIBUTION COEFFICIENT – LAB 6
Equiv. wt. of acetic acid = ______ g/mol
a. Volume of base required for first titration ________ mL = ________ L
b. Mass of acetic acid in the 10 mL aliquot ________ g
Formula: massacid = (N x V)base x (Equiv. wt.)acid
c. Volume of base required for second titration ________ mL = ________ L
d. Mass of acid left over in water layer ________ g
Use the same formula as in (b) g AcOH in H2O
e. Mass of acid in ethyl acetate after a single 10 mL extraction ________ g
Item (b) – item (d) g AcOH in EtOAc
1 x 10 ml extraction
(starting g AcOH in 10 mL aliquot – g AcOH remaining in H2O = g AcOH in EtOAc)
f. Volume of base required for third titration ________ mL = ________ L
g. Mass of acid in water layer ________ g
Use the same formula as in (b) g AcOH in H2O
h. Mass of acid in ethyl acetate after two 5 mL extractions ________ g
Item (b) – item (g) g AcOH in EtOAc
2 x 5 ml extractions
i. Distribution coefficient (Kp) of acetic acid in ethyl acetate
Item (e) / item (d) Item (h) / Item (g)
Kp (single extraction) ________ versus Kp (double extraction) ________

9. Spring 2013
DEHYDRATION OF TERT-AMYL ALCOHOL (2-METHYL-2-BUTANOL) – LAB 8
The synthetic procedure is identical to the one used for the dehydration of
cyclohexanol to cyclohexene (p. 123). In this experiment, however, two isomers will be
formed instead of one.
2-methyl-2-butanol
2-methyl-2-butene
2-methyl-1-butene
OH
H2SO4
OH2
+
H2O
+
Procedure
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.

10. Spring 2013
13. Calculate the % yield of the mixture of alkene isomers.
14. Add 5-10 drops of the distillate into 5 drops of 1% KMnO4 in a test tube. Record your
observations. Add 5-10 drops of the distillate into 5 drops of 1% Br2/H2O in a
separate test tube. Record your observations.
15. Check with your instructor first! Obtain a gas chromatogram of the isomeric mixture.
Compare (if available) with pure samples of the two isomers formed. Calculate the
relative % of the isomers formed.
Questions
1) Write the reactions that represent the addition of KMnO4 and Br2 to the two alkenes.
2) Draw the full mechanism (with arrow pushing) for the dehydration of tert-amyl
alcohol that leads to the formation of both products.
3) 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
4) 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
5) What alcohol would be the most appropriate starting material for the synthesis of 1-
methylcyclohexene? Draw the reaction scheme.