QUEENSBOROUGH COMMUNITY COLLEGE
CHEMISTRY DEPARTMENT
COURSE OUTLINE
CH-252
ORGANIC CHEMISTRY II
Hours: 3 Class Hours
4 Laboratory Hour
1 Recitation Hour
5 Credits
Pre-requisites: CH-151,152, and 251
Course Description:
A continuation of CH-251, this course develops the relationship between properties and
structure of organic compounds in greater detail. In addition, current syntheses, modern
mechanisms of organic reactions, and spectroscopic identification of compounds are
discussed. The main families of organic compounds of bio-chemical interest and their
typical reactions are studied. Laboratory work involves the synthesis, purification, and
identification of organic compounds, as well as organic qualitative analysis.
Curricula for which the course is required/recommended:
A.S. Degree Programs in Liberal Arts and Sciences (Science and Mathematics),
Engineering Science, Health 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 the
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 introduce students to the logic of organic chemistry by
selecting the topics and developing them systematically. To best achieve this objective,
is to provide students with a framework that entices them to gather their thoughts to
better understand the relationship between structure and function. There is great
emphasis of biological applications throughout this course. Use of computer graphics
can assist students to visually understand of intricate connection between structure and
properties.
Texts:
ORGANIC CHEMISTRY, 8TH EDITION, L. G. Wade, Pearson,
ISBN #: 978-0-321-76841-8
WORKBOOK PROBLEMS FOR ORGANIC CHEMISTRY, Sarlo &
Svoronos, Wm. C. Brown Publishers, ISBN 0072899689
LAB
MANUAL:
ORGANIC CHEMISTRY LABORATORY MANUAL, 2ND ED.
P. Svoronos, E. Sarlo and R. J. Kulawiec, Wm. C. Brown Publishers
ISBN 0-697-33923-8
Spring 2013
CH-252: Organic Chemistry II
Methods by which student learning will be evaluated:
The general guidelines for assessing grades are as follows:
o Examinations, Assignments and Classroom Performance
o Laboratory Work
o Final Examination
50%
25%
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 during the last laboratory period (check-out,
week 14). 10% of that grade will be added to the student’s final course grade. The ACS
exam can not lower the 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 Science Building, room 132 (718-6316257) 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 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. 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.
CH-252: ORGANIC CHEMISTRY II

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.
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. 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-252: ORGANIC CHEMISTRY II
LECTURE SCHEDULE
CHAPTER
TOPIC
HOURS
15
Conjugated Systems
2
16
Aromatic Compounds
3
17
Reactions of Aromatic Compounds
4
12
Infrared Spectroscopy and Mass Spectrometry
4
13
Nuclear Magnetic Resonance Spectroscopy
6
18
Ketones and Aldehydes
10
19
Amines
5
20
Carboxylic Acids
3
21
Carboxylic Acid derivatives
5
22
Condensation and Alpha Substitutions of Carbonyl
Compounds
4
23
Carbohydrates
4
24
Amino Acids, Peptides, and Proteins
4
25
Lipids
2
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.
CH-252: ORGANIC CHEMISTRY II
LABORATORY SCHEDULE
WEEK
TOPIC
EXPERIMENT
PAGE
1
Check-in; Introduction to Organic
Chemistry II Lab
---
2
Diels Alder Reaction and
Reactions of Acetylene
12
11
147
141
3
Nitration of Acetanilide
---
handout*
4
Synthesis of 2,4-Dinitrophenyl aniline
15.3
195
5
Oxidation of Cyclohexanol to
Cyclohexanone
17.1
223
6
Reduction of Cyclohexanone to
Cyclohexanol
17.2
226
7
Qualitative Tests for Alcohols
14.2
180
8
Equivalent Weight of Organic Acids
Hydrolysis of Benzonitrile
16.1
16.2
204
211
9
Synthesis of Aspirin
Saponification of an Ester
16.3
16.6
214
221
10
Imides: Synthesis of N-phenylphthalimide
16.5
219
11
Synthesis of Cyclopentanone from
Adipic Acid
18.2
247**
12
The Aldol Condensation:
Synthesis of Dibenzalacetone Michael addition
18.1
243
18.3
249
13
Synthesis of Acetanilide
Azo Dye Formation
19.2
19.3
255
258
14
ACS Exam
---
15
Check-out
---
* see next page for the handout; ** make sure to grease all glassware very thoroughly
Nitration of Acetanilide – WEEK 2
Procedure (Taken from Experimental Organic Chemistry, Theory and Practice, Charles F.
Wilcox, Jr. Macmillan Publishing Co., page 328.)
In a 125-mL Erlenmeyer flask dissolve 6.8g (0.05 mole) of pure acetanilide in 8 mL of glacial
acetic acid by warming it gently. Cool the warm solution until crystals begin to form and then
add slowly, while swirling the solution, 10 mL of ice-cold concentrated sulfuric acid. Prepare in
nitrating mixture by adding 3.5mL (5g, 0.06 mole) of concentrated nitric acid to 5 mL of cold
concentrated sulfuric acid; cool the solution to room temperature and transfer it to a small
separatory funnel.
Cool the acetanilide solution to 5◦ in an ice bath, remove the flask from the bath, and add the
nitrating mixture slowly, drop by drop. Swirl the reaction mixture to obtain good mixing in the
viscous solution and do not permit the temperature to rise above 20-25◦. After all of the nitrating
mixture has been added, allow the solution to stand at room temperature for about 40 min (but
not longer than 1 hr) to complete the reaction. Pour the solution slowly with stirring into a
mixture of 100 mL of water and 20-25g of chipped ice. Collect the product with suction, press it
firmly on filter, and transfer the filter cake to a beaker. Mix the crystals thoroughly with about
75 mL of water to form a thin paste, return them to the suction filter, and wash thoroughly with
more water to remove the nitric and sulfuric acids. Press the material as dry as possible. The
crude, moist p-nitroacetanilide is sufficiently pure to be used directly for hydrolysis to pnitroaniline. The moist product is equivalent to about 6 g of dry material.
A small portion of the material may be purified by crystallization from 80% aqueous ethanol,
with the addition of a little decolorizing carbon. The melting point of p-nitroacetanilide is about
215-216◦; use a metal block or MEL-TEMP unit.
Questions
1. Write a mechanism for nitration of acetanilide to p-nitroacetanilide.
2. What product(s) are formed by nitration of the following?
a)
b)
c)
d)
p-acetotoluidide
m-acetotoluidide
m-cresol
p-toluic acid