CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
QCC COURSE ASSESSMENT FORM
Date of Assessment: Fall 2011 and Spring 2012
Department: Chemistry
Course: CH-251
Curriculum or Curricula: LS1, PE1, HS1, SF1
Submitted: Fall 2012
PART I. STUDENT LEARNING OBJECTIVES
For Part I, attach the summary report (Tables 1-4) from the QCC Course Objectives Form.
TABLE 1. EDUCATIONAL CONTEXT
This course is the first part of the two semester organic chemistry sequence. The objective of this course is to gradually and
logically develop the relationships between structure and properties of organic compounds with emphasis on reaction
mechanisms, stereochemistry, and synthesis. In addition, the course contains a laboratory component which serves to
introduce the student to organic chemistry techniques and analytical methods. While working in groups the student transitions
from learning simple laboratory practices to mastering the more sophisticated procedures which will be needed during the
second semester. This course is intended for those students pursuing A.S. degrees in Liberal Arts and Sciences (Science and
Mathematics), Engineering Science, Health Sciences, Forensics, Pharmaceutical Sciences and Environmental Health. It is
also appropriate for post-undergraduate students interested in pre-medical, pre-dental, pre-veterinary, pre-pharmacy, prechiropractic, pre-physician and other related fields.
TABLE 2. CURRICULAR OBJECTIVES
Note: Include in this table curriculum-specific objectives that meet Educational Goals 1 and 2:
Curricular objectives addressed by this course:
1.
Demonstrate proficiency in factual knowledge and conceptual understanding required for transfer to the junior year in a baccalaureate
program in natural science, mathematics, engineering, or computer science or any other program in health sciences. (LS1, PE1)
2.
Demonstrate proficiency in communication skills, including technical writing and oral presentation. (LS1, PE1)
3.
Apply concepts through use of current technology. (LS1)
4.
Demonstrate an understanding of the professional, ethical, and social responsibilities related to the fields of natural science, forensic
science, mathematics, engineering, and /or computer science. (LS1, PE1, SF1)
5.
Demonstrate proficiency in acquiring, processing and analyzing information in all its forms as related to the field of concentration. (LS1)
6.
Use analytical reasoning skills and apply logic to solve problems. (PE1)
7.
Use quantitative skills and mathematical reasoning to solve problems. (PE1)
8.
Students will communicate effectively through reading, writing, listening and speaking. (SF1)
9.
Students will demonstrate competency in the concepts and methods of the foundation of organic chemistry required for transfer to the
junior year in Forensic Science at John Jay College. (SF1)
10. Students will apply concepts learned in the classroom and make conclusions based on scientific thinking. (SF1)
11. Students will work collaboratively in the laboratory to provide reasonable analysis of data obtained and to solve problems. (SF1)
12. Students will integrate the knowledge and skills gained in previous courses with subsequent courses to establish an all-around
scientific background. (SF1)
1
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
13. Demonstrate an understanding of the principles of chemistry and how they are fundamental to all living systems. (HS1)
TABLE 3. GENERAL EDUCATION OBJECTIVES
Gen Ed objective’s
ID number from list General educational objectives addressed by this course: Select from preceding list.
(1-10)
1.
Communicate effectively through reading, writing, listening and speaking.
2.
Use analytical reasoning to identify issues or problems and evaluate evidence in order to make informed decisions.
5.
Integrate knowledge and skills in their program of study.
7.
Work collaboratively in diverse groups directed at accomplishing learning objectives.
9.
Employ concepts and methods of the natural and physical sciences to make informed judgments.
TABLE 4: COURSE OBJECTIVES AND STUDENT LEARNING OUTCOMES
Course objectives
Learning outcomes
1. To draw organic
compounds in a variety of
representations.
a. Students will learn to draw Lewis structures and line angle structures.
b. Students will learn to draw in three dimensional representations, including using VSEPR
geometry, ring conformations, Newman projections, and Fischer projections.
2. To learn about acids and
bases as they pertain to
organic compounds.
a. Students will learn the concepts associated with Lewis and Brønsted acids and bases.
b. Students will use their knowledge of acids and bases to be able to predict the products and
direction of equilibrium reactions.
c. Students will be able to identify the nucleophile and electrophile in a reaction and use this
knowledge to predict the outcome of the reaction.
a. Students will learn how to recognize the functional groups present in organic compounds.
3. To learn the functional
groups that are common in b. Students will be able to identify different representations of the functional groups.
organic compounds and
c. Students will learn the proper IUPAC nomenclature of organic compounds containing
how to name them.
functional groups.
4. To learn the energetics of
chemical reactions.
a. Students will learn to draw an energy diagram and label the appropriate features.
b. Students will be able to interpret an energy diagram and predict whether a reaction is
endothermic or exothermic.
c. Students will learn the factors that influence the rate of a reaction including catalysts,
temperature, solvents, and the structure of the substrate.
d. Students will be exposed to the different types of reactive intermediates including
carbocations, carbanions, radicals, and carbenes.
5. To study the
stereochemistry of
molecules.
a. Students will learn to represent an organic molecule in three dimensions.
b. Students will be able to assign spatial relationships between two molecules, including
different types of isomers.
c. Students will learn to use molecular model kits as a visual aid in drawing and assigning
stereochemistry.
d. Students will be exposed to the importance of optical activity in both chemical and biological
applications.
2
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
a. Students will use the conventional methods of electron movement using arrows.
b. Students will represent resonance structures using arrows and their understanding of
electron movement.
6. To understand the basics of
the movement of electrons. c. Students will be able to identify key transition states and intermediates during the course of
a reaction.
d. Students will use their knowledge of the mechanistic details of a reaction to be able to
predict the products of other similar reactions.
7. To learn the chemical
transformations that are
common to each of the
functional groups.
a. Students will learn how to synthesize key functional groups including alkanes, alkenes,
alkynes, alcohols, aldehydes, ketones, carboxylic acids, ethers, and sulfides.
b. Students will learn the transformation of key functional groups including alkanes, alkyl
halides, alkenes, alkynes, alcohols, ethers, and sulfides.
c. Students will learn the broad classes of reaction types including substitution, elimination,
addition, and rearrangement reactions.
d. Students will be able to predict the product of a reaction when given the starting material(s)
and reagents.
e. Students will be able to predict the starting material(s) of a reaction when given product(s)
and reagents.
f. Students will be able to predict the reagents necessary to convert from starting material(s)
to product(s).
8. To write multiple-step
syntheses and
retrosyntheses.
a. Students will be able to combine reactions that they have learned into a multi-step
synthesis.
b. Students will be able to examine a complex molecule and dissect it into smaller components
and then reassemble them.
c. Students will apply lessons they learned in previous chapters to unfamiliar molecules.
9. To learn the common
safety practices and
laboratory techniques
a. Students are required to watch a safety video approved by the American Chemical Society
and to pass a safety quiz.
b. Students will learn the location and proper use of all safety-related equipment.
c. Students will learn the importance of proper attire as it pertains to safety in the laboratory
setting. This includes wearing safety goggles and personal protective equipment.
d. Students will learn the proper disposal of chemical waste.
e. Students will come to lab having written a pre-lab report summarizing the experiment and
safety measures to ensure that they have read the procedure beforehand and are prepared
for the lab.
a. Students will perform key techniques in organic synthesis including distillation, separation
and extraction, recrystallization, and titration.
10. To understand common
b. Purification techniques are reinforced throughout the semester as students perform
laboratory techniques used
experiments.
in organic synthesis
c. Students will connect the practical application of a reaction learned in the lab to the
theoretical discussion in the classroom.
11. To learn to apply critical
thinking, proper scientific
writing, and rational
analysis of the data.
a. Students are required to submit a pre-lab report at the beginning of each lab.
b. Students are required to submit a complete post-lab report at the end of each lab using
proper scientific writing.
c. Students will make observations and collect data during the lab.
d. Students will then analyze the data obtained in the lab, critically assess the data, and
summarize their findings in their lab report.
e. Student learning will be assessed through assigned questions related to aspects of the lab.
3
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
12. To work collaboratively in
diverse groups to achieve
a common goal
Prepared by Julie Pigza and John Regan
a. Students will work in small groups during each laboratory period to achieve the objectives of
the experiment.
b. Each student will be involved in all aspects of the experimental setup and data acquisition.
c. Students will be individually responsible for writing their own lab report.
PART II. ASSIGNMENT DESIGN: ALIGNING OUTCOMES, ACTIVITIES, AND ASSESSMENT TOOLS
For the assessment project, you will be designing one course assignment, which will address at least one general
educational objective, one curricular objective (if applicable), and one or more of the course objectives. Please identify these in
the following table:
TABLE 5: OBJECTIVES ADDRESSED IN ASSESSMENT ASSIGNMENT
Course Objective(s) selected for assessment: (select from Table 4)
1. To draw organic compounds in a variety of representations.
2. To learn about acids and bases as they pertain to organic compounds.
6. To understand the basics of the movement of electrons.
7. To learn the chemical transformations that are common to each of the functional groups.
Curricular Objective(s) selected for assessment: (select from Table 2)
6. Use analytical reasoning skills and apply logic to solve problems. (PE1)
10. Students will apply concepts learned in the classroom and make conclusions based on scientific thinking. (SF1)
12. Students will integrate the knowledge and skills gained in previous courses with subsequent courses to establish an allaround scientific background. (SF1)
General Education Objective(s) addressed in this assessment: (select from Table 3)
GE#2: Use analytical reasoning to identify issues or problems and evaluate evidence in order to make informed decisions.
GE#5: Integrate knowledge and skills in their program of study.
GE#9: Employ concepts and methods of the natural and physical sciences to make informed judgments.
In the first row of Table 6 that follows, describe the assignment that has been selected/designed
for this project. In writing the description, keep in mind the course objective(s), curricular
objective(s) and the general education objective(s) identified above,
Also in Table 6, please
a) identify the three to four most important student learning outcomes (1-4) you expect from
this assignment
b) describe the types of activities (a – d) students will be involved with for the assignment, and
c) list the type(s) of assessment tool(s) (A-D) you plan to use to evaluate each of the student
outcomes. (Classroom assessment tools may include paper and pencil tests, performance
assessments, oral questions, portfolios, and other options.)
Note: Copies of the actual assignments (written as they will be presented to the students) should be
gathered in an Assessment Portfolio for this course.
4
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
TABLE 6: ASSIGNMENT, OUTCOMES, ACTIVITIES, AND ASSESSMENT TOOLS
Briefly describe the assignment that will be assessed:
The KPRS Assessment Exam for Organic Chemistry 1:
The exam was collectively written by the organic faculty members at QCC. Students will take this exam at
the end of the semester. One of the selected exam questions surveys a general chemistry concept that is
highly pertinent to organic chemistry. Three of the exam questions have been selected to represent
fundamental concepts in organic chemistry. The selected problems require students to integrate knowledge
learned in the classroom and apply logical reasoning towards problems common in organic chemistry. They
also represent some of the topics that are critical to student success in subsequent organic and
biochemistry courses. In particular, the exam will test the student’s knowledge of acids and bases and
electron movement as it pertains to mechanistic behavior and resonance structures. The exam questions
are a mixture of multiple choice and short answer questions including drawing two dimensional
representations of three dimensional organic structures.
Desired student learning
outcomes for the assignment
(Students will…)
List in parentheses the Curricular
Objective(s) and/or General
Education Objective(s) (1-10)
associated with these desired
learning outcomes for the
assignment.
Briefly describe the range of
activities student will engage
in for this assignment.
What assessment tools will be
used to measure how well
students have met each
learning outcome? (Note: a
single assessment tool may be
used to measure multiple
learning outcomes; some
learning outcomes may be
measured using multiple
assessment tools.)
1. Students will integrate and
expand on the knowledge
learned in general chemistry as it
applies to organic chemistry
(Gen Ed Objectives (GEO)
#2,5,9; Curricular Objectives
(CO) #6,10,12)
2. Students will understand and
apply terms describing the
movement of electrons as they
pertain to resonance and the
drawing of acceptable Lewis
structures (GEO #2,5,9; CO
#6,10,12).
3. Students will understand and
apply terms describing the
general subtypes of key organic
reactions and the mechanistic
details associated with each
(GEO #2; CO #6,10).
A. Student responses will be
a. Students will attend class to
analyzed on four selected
learn necessary concepts.
exam
problems from the
b. Students ability to integrate
KPRS assessment exam.
knowledge will be tested
Students’ answers will be
throughout the semester on
correlated
to their level of
regular exams and will
understanding of the
receive instructor feedback.
particular concepts.
c. Students will be assigned
homework problems
pertaining to the important
concepts learned during the
semester.
d. Students will apply theoretical
concepts learned in the
classroom in a laboratory
setting.
e. Students will take the KPRS
Assessment Exam for
Organic Chemistry I at the
end of the semester.
5
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
4. Students will be able to draw in a
variety of three dimensional
representations (CO #10).
5. Students will be able to draw the
movement of electrons as it
pertains to the mechanism of a
reaction (CO #10).
6. Students will learn how to
recognize the functional groups
present in organic compounds
(GEO #9; CO #6,10).
7. Students will use the concepts
learned and apply them towards
an unfamiliar organic structure
(GEO #2,5,9; CO #6,10)
PART III. ASSESSMENT STANDARDS (RUBRICS)
TABLE 7: CH-251: Assessment Standards (Rubrics)
Brief description of assignment: (Copy from Table 6 above)
The KPRS Assessment Exam for Organic Chemistry 1:
The exam was collectively written by the organic faculty members at QCC. Students will take this exam at
the end of the semester. One of the selected exam questions surveys a general chemistry concept that is
highly pertinent to organic chemistry. Three of the exam questions have been selected to represent
fundamental concepts in organic chemistry. The selected problems require students to integrate knowledge
learned in the classroom and apply logical reasoning towards problems common in organic chemistry. They
also represent some of the topics that are critical to student success in subsequent organic and
biochemistry courses. In particular, the exam will test the student’s knowledge of acids and bases and
electron movement as it pertains to mechanistic behavior and resonance structures. The exam questions
are a mixture of multiple choice and short answer questions including drawing two dimensional
representations of three dimensional organic structures.
Desired student learning outcomes
(Copy from Column 1, Table 6 above;
include Educational Goals and/or General
Education Objectives addressed)
Assessment measures for each
learning outcome
(Copy from Column 3,Table 6 above)
Standards for student performance:
 Describe the standards or rubrics
for measuring student
achievement of each outcome in
the assignment.
 Give the percentage of the class
that is expected to meet these
outcomes
If needed, attach copy(s) of rubrics.
1. Students will integrate and
expand on the knowledge
learned in general chemistry as
it applies to organic chemistry
(Gen Ed Objectives (GEO)
A. Student responses will be
analyzed on four selected
exam problems from the
KPRS assessment exam.
Students’ answers will be
Each question requires the student to
make use of learned fundamental
knowledge. Each response on the
selected questions is assigned a
performance level (point value) of 0-3
based on how completely the question
6
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
2.
3.
4.
5.
6.
7.
#2,5,9; Curricular Objectives
(CO) #6,10,12)
Students will understand and
apply terms describing the
movement of electrons as they
pertain to resonance and the
drawing of acceptable Lewis
structures (GEO #2,5,9; CO
#6,10,12).
Students will understand and
apply terms describing the
general subtypes of key organic
reactions and the mechanistic
details associated with each
(GEO #2; CO #6,10).
Students will be able to draw in
a variety of three dimensional
representations (CO #10).
Students will be able to draw the
movement of electrons as it
pertains to the mechanism of a
reaction (CO #10).
Students will learn how to
recognize the functional groups
present in organic compounds
(GEO #9; CO #6,10).
Students will use the concepts
learned and apply them towards
an unfamiliar organic structure
(GEO #2,5,9; CO #6,10)
Prepared by Julie Pigza and John Regan
has been answered.
correlated to their level of
understanding of the particular
• Three points indicates that the
concepts.
student can successfully solve all
aspects of the problem.
• Two points indicates that the
student understood most of the
necessary concepts but missed one
key aspect needed to solve the
problem.
• One point indicates that the student
missed two key aspects that were
necessary to solve the problem.
• Zero points indicate that the student
either did not recognize the type of
problem presented or missed more
than two key aspects necessary to
solve the problem.
See rubric below.
Projected outcomes:
Question #3
Learning outcomes #1
• 60% expected to be 3
• 25% expected to be 2
• 10% expected to be 1
• 5% expected to be 0
Question #5
Learning outcomes #1, 2
• 30% expected to be 3
• 40% expected to be 2
• 20% expected to be 1
• 10% expected to be 0
Question #10
Learning outcomes #3, 5, 6, 7
• 40% expected to be 3
• 35% expected to be 2
• 20% expected to be 1
• 5% expected to be 0
Question #11
Learning outcomes #3, 4, 6, 7
• 30% expected to be 3
• 45% expected to be 2
• 20% expected to be 1
• 5% expected to be 0
7
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
RUBRIC FOR SELECTED QUESTIONS ON THE KPRS ASSESSMENT EXAM FOR CH-251
Question 3. General Chemistry Concepts:
Which of the following is a Lewis base?
a) BF 3
b) P(CH 3 ) 3
Choice
A
B
C
D
c) NH 4 +
d) H 3 O+
Performance
Evaluation
level
Unable to recognize that boron does not have a lone pair and therefore does not
0
meet any of the requirements to be a Lewis base
3
Correct response
Unable to recognize that nitrogen does not have a lone pair when it is a cation
1
but did understand that nitrogen, when neutral, does have a lone pair and can be
considered a Lewis base.
Realizes that oxygen has two lone pairs but fails to understand that oxygen as a
2
cation, even though it has one remaining lone pair, cannot function as a Lewis
base
Question 5. Resonance Concepts:
Draw three resonance structures for azide, N 3 –. Make sure to include all bonds and lone pairs and any
formal charges. Which of these three is the least contributing structure and briefly explain why?
Performance
Evaluation
level
Correctly drew all three resonance structures; this included considering the total number of
3
electrons, all bonds and lone pairs, all formal charges, and followed the octet rule AND
understood which was the least contributing resonance structure.
Correctly drew two resonance structures with all of the above requirements OR missed one
2
aspect above (bonds/lone pairs/formal charge)
Missed two or more key aspects, violated the octet rule, and incorrectly assigned the least
1
contributing resonance structure.
Minimally understands the concept of electron movement and cannot draw resonance
0
structures
Question 10. Mechanism Concepts:
Draw the mechanism, with arrow pushing, of the following S N 1 reaction. (See attached assessment exam
for the structures used in the reaction).
Performance
Evaluation
level
Correctly showed the movement of electrons using arrows to indicate: 1) the loss of the
3
bromide to form a carbocation, 2) to show a rearrangement of the carbocation to form a
more stable carbocation, 3) addition of the solvent to the carbocation, and 4) proton transfer
8
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
2
1
0
Prepared by Julie Pigza and John Regan
from the oxonium ion to solvent to yield the indicated product. In addition, all intermediates
have the correct charge.
Arrows missing to show one of the key steps above and/or used arrows in the wrong
direction in one step.
Arrows missing to show two of the key steps above and/or used arrows in the wrong
direction in two steps and/or charges were missing or were incorrect on key intermediates.
Does not understand the concept of electron movement, the S N 1 reaction, and the ability to
form a more stable carbocation intermediate.
Question 11. Reaction Concepts:
Predict the product(s) of the following reaction. (See attached assessment exam for the structures used in
the reaction).
Performance
Evaluation
level
Correctly identified the reaction as an E2 reaction and showed the alkene in the appropriate
3
location in the product.
Correctly identified the reaction as an E2 reaction but showed the alkene in the wrong
2
position.
Incorrectly showed the product of an S N 2 reaction and failed to realize it was an E2
1
reaction.
0
The product drawn does not represent either an E2 or S N 2 reaction.
PART IV. ASSESSMENT RESULTS
TABLE 8A: CH-251: Summary of Assessment Results, Academic Year 2011-2012, N=46 students for 3 sections (3
instructors) and N=26 students for 2 sections (2 instructors)
Question 3 (N=46)
Performance Level
B (correct)
3
D
2
Evaluation
Correct response
Realizes that oxygen has
two lone pairs but fails to
understand that oxygen
as a cation, even though
it has one remaining lone
pair, cannot function as a
Lewis base
Unable to recognize that
nitrogen does not have a
lone pair when it is a
cation but did
understand that nitrogen,
when neutral, does have
a lone pair and can be
considered a Lewis
base.
Unable to recognize that
boron does not have a
lone pair and therefore
does not meet any of the
requirements to be a
Lewis base
# of Students
Outcome: 2011-2012
Actual (Expected)
20
2
11
13
43% (60%)
5% (25%)
24% (10%)
28% (5%)
Question 5 (N=26)
Performance Level
(correct)
3
Evaluation
Correctly drew all three
resonance structures;
this included
2
Correctly drew two
resonance structures
with all of the above
C
1
1
Missed two or more key
aspects, violated the
octet rule, and incorrectly
A
0
0
Minimally understands
the concept of electron
movement and cannot
9
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
considering the total
number of electrons, all
bonds and lone pairs,
all formal charges, and
followed the octet rule
AND understood which
was the least
contributing resonance
structure.
requirements OR missed
one aspect above
(bonds/lone pairs/formal
charge)
2
6
10
8
8% (30%)
23% (40%)
38% (20%)
31% (10%)
Question 10 (N=26)
Performance Level
(correct)
3
2
1
0
Evaluation
Correctly showed the
movement of electrons
using arrows to
indicate: 1) the loss of
the bromide to form a
carbocation, 2) to show
a rearrangement of the
carbocation to form a
more stable
carbocation, 3) addition
of the solvent to the
carbocation, and 4)
proton transfer from the
oxonium ion to solvent
to yield the indicated
product. In addition, all
intermediates have the
correct charge.
Arrows missing to show
one of the key steps
above and/or used
arrows in the wrong
direction in one step.
Arrows missing to show
two of the key steps
above and/or used
arrows in the wrong
direction in two steps
and/or charges were
missing or were incorrect
on key intermediates.
Does not understand the
concept of electron
movement, the S N 1
reaction, and the ability
to form a more stable
carbocation
intermediate.
5
8
7
6
19% (40%)
31% (35%)
27% (20%)
23% (5%)
(correct)
3
2
1
0
# of Students
Outcome: 2011-2012
Actual (Expected)
# of Students
Outcome: 2011-2012
Actual (Expected)
Question 11 (N=26)
Performance Level
Evaluation
# of Students
Outcome: 2011-2012
Actual (Expected)
Correctly identified the
reaction as an E2
reaction and showed
the alkene in the
appropriate location in
the product.
Correctly identified the
reaction as an E2
reaction but showed the
alkene in the wrong
position.
assigned the least
contributing resonance
structure.
Incorrectly showed the
product of an S N 2
reaction and failed to
realize it was an E2
reaction.
draw resonance
structures
The product drawn does
not represent either an
E2 or S N 2 reaction.
9
2
13
2
34% (30%)
8% (45%)
50% (20%)
8% (5%)
10
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
TABLE 8B: SUMMARY OF ASSESSMENT RESULTS
Desired student learning outcomes:
(Copy from, Column 1,Table 6 above;
include Educational Goals and/or General
Education Objectives addressed)
Student achievement: Describe the group achievement of
each desired outcome and the knowledge and cognitive
processes demonstrated.
1. Students will integrate and expand on
the knowledge learned in general
chemistry as it applies to organic
chemistry (Gen Ed Objectives (GEO)
#2,5,9; Curricular Objectives (CO)
#6,10,12)
2. Students will understand and apply
terms describing the movement of
electrons as they pertain to resonance
and the drawing of acceptable Lewis
structures (GEO #2,5,9; CO #6,10,12).
3. Students will understand and apply
terms describing the general subtypes
of key organic reactions and the
mechanistic details associated with
each (GEO #2; CO #6,10).
4. Students will be able to draw in a
variety of three dimensional
representations (CO #10).
5. Students will be able to draw the
movement of electrons as it pertains to
the mechanism of a reaction (CO #10).
6. Students will learn how to recognize
the functional groups present in
organic compounds (GEO #9; CO
#6,10).
7. Students will use the concepts learned
and apply them towards an unfamiliar
organic structure (GEO #2,5,9; CO
#6,10)
Question #3 on the exam tested learning outcome #1: 43%
of students scored 3, 5% scored 2, 24% scored 1, and 28%
scored 0. The number of students who scored 3 were slightly
lower than the expected outcome. More students scored 1’s
and 0’s than was expected. This problem tested the students’
knowledge of acids and bases and the distinction between the
different subtypes, their ability to represent the molecule with
the appropriate bonding and lone pairs, and to make the
connection from concepts originally learned in general
chemistry and used in a different context in organic chemistry.
Question #5 on the exam tested learning outcomes #1 and
2: 8% of students scored 3, 23% scored 2, 38% scored 1, and
31% scored 0. It was expected that 70% of the students would
get the problem completely or mostly correct (score of 3 or 2).
However, the actual percentage was 31%. This problem
tested the students’ ability to expand on the concept of
resonance, as taught in general chemistry, and apply it to a
structure used in organic chemistry. Students had to use their
knowledge of electron movement to correctly draw all three
Lewis structures.
Question #10 on the exam tested learning outcomes #3, 5,
6, and 7: 19% of students scored 3, 31% scored 2, 27%
scored 1, and 23% scored 0. The results for the scores in the
middle range were similar to the expected outcome. Results
for a score of 3 were much lower than expected, while results
of score 0 were higher than expected. This problem tested the
students’ ability to apply electron movement as it pertains to
key mechanistic details involving particular functional groups
in a previously unseen structure.
Question #11 on the exam tests learning outcomes #3, 4, 6,
and 7: 34% of students scored 3, 8% scored 2, 50% scored 1,
and 8% scored 0. The results were within our expectations for
a score of 3. The low number of students scoring a 2 and the
high number of students scoring 1 was unexpected. This
problem tested the students’ ability to use functional groups
present in a molecule along with the reaction conditions to be
able to predict the product of the reaction.
11
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
TABLE 9. EVALUATION AND RESULTING ACTION PLAN
In the table below, or in a separate attachment, interpret and evaluate the assessment results, and
describe the actions to be taken as a result of the assessment. In the evaluation of achievement,
take into account student success in demonstrating the types of knowledge and the cognitive
processes identified in the Course Objectives.
Following the assessment that took place in the academic year 2011-2012, the course instructors met and
discussed the report and the conclusions drawn from the report. The instructors discussed ways to improve
student learning on the key concepts that had been tested and discussed the format of the assessment
test.
A. Analysis and interpretation of assessment results:
What does this show about what and how the students learned?
Question #3: This problem tested the students’ knowledge of acids and bases and the distinction between
the different subtypes. In particular, it focused on the concept of Lewis bases and required students to
understand the meaning of the term. To answer the question, students should have drawn the Lewis
structure of the compound taking note of the lone pairs of electrons on the central atom. Half of the
students got the answer correct or mostly correct. Of the students who missed the question, 25% picked a
compound in which the central atom usually has a lone pair (but in this example did not) and the remaining
25% picked a compound in which the central atom never has a lone pair. This shows one of two things:
either the instructors overestimated the amount of information the students retained from general chemistry
or that students were not drawing the compound but likely just guessing based on the atoms.
Question #8: This problem tested the students’ ability to expand on the concept of resonance, as taught in
general chemistry, and apply it to a structure used in organic chemistry. Students had to use their
knowledge of electron movement to correctly draw three Lewis structures and to assign formal charges.
Only 30% understood the question well enough to be able to write most of the aspects needed to solve the
problem. In contrast, 70% of the students missed several aspects needed to solve the problem and violated
a key rule used when drawing resonance structures. At first glance, it seems that the students do not
understand the concept of resonance. However, upon further inspection, the particular molecule chosen
was made more difficult because the bonding order of the three atoms was not given. This question
therefore may not accurately reflect the student’s understanding of the concept of resonance.
Question #10: This problem tested the students’ ability to apply electron movement as it pertains to key
mechanistic details involving functional groups. The molecule used is one in which the students have never
seen so they have to apply the concepts they learned to a previously unseen structure. The students were
given the reactant and product and had to show how to get from one to the other using arrows.
Approximately half of the students got the question correct or mostly correct and understood the process of
electron movement and bond formation. The remainder of students were split between either not
understanding the reaction type or did not accurately show the movement of electrons. The students who
did not draw arrows at all show a lack of understanding of how the movement of electrons can be used to
show the transformation of reactant to product. Students who drew arrows in the wrong way but still had the
correct key intermediates understood the importance of bond formation but were unclear on the correct
electron movement to account for this.
12
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
Question #11: This problem tested the students’ ability to use functional groups present in a molecule
along with the reaction conditions to be able to predict the product of the reaction. The students had to
recognize the role of the added reagents, the 3D conformation of the substrate, and the subtle interplay of
these two factors on the distribution of products. Students had to also recognize that the key category of
the reaction was an elimination reaction and not a substitution reaction. Approximately 40% of the students
correctly identified the products resulting from an elimination reaction. Half of the students incorrectly drew
the product of a substitution reaction. While the reagents given could be used for either an elimination or
substitution, the substrate limited the reaction to only be an elimination reaction. Students who missed the
problem did not correctly identify the effect of the substrate on the outcome of the reaction.
B. Evaluation of the assessment process:
What do the results suggest about how well the assessment test and the assessment process worked to
show what the students have learned?
The assessment test and grading
The assessment process involved designing the KPRS assessment test through consultation with all
members of the organic faculty. The finalized assessment test was taken by the students in the lecture
portion of the course at the end of the semester. To encourage the students, bonus points were awarded to
the final exam score. Students were given one hour to complete the full assessment test. Four questions
were chosen for the assessment to represent the four major categories that the learning outcomes of the
course fall within. Rigorous rubrics were created to assess the four questions and assign a score for each
question. The rubrics were based on the important aspects identified within each question and represent
learning goals of the course.
Evaluation of student learning
The goal of the assessment test was to critically evaluate student learning in four major categories. These
categories represent fundamental concepts and expected learning outcomes of a student at the end of the
first semester of the organic sequence. Organic chemistry as a course introduces central concepts in the
first few chapters of the textbook and these concepts are reinforced throughout the semester through the
use of more complex examples. The first two questions represent these fundamental concepts while the
third and fourth questions probe a deeper understanding as applied to more complex molecules. The
percentage of students getting the correct or mostly correct answer on the first two questions was similar to
the last two questions. This indicated that even though the material was more difficult, the fact of continual
reinforcement of key concepts was beneficial. As the course material becomes more complicated, shortcuts
are taken to give enough time to present the new material. These shortcuts include not drawing bonds, full
structures, atoms, and/or electrons. These shortcuts are taken by the professor and the textbook and the
students are therefore exposed to them. While the professor and textbook understand the concepts implied
within these shortcuts, often times the students fail to grasp or appreciate the underlying material. In
addition, the underlying material may not be explicitly restated during class. This line of reasoning can help
us to understand student learning and to evaluate their answers as given on the assessment exam. This
can explain why students fell short of our expectations on the first two questions. The process of
assessment clearly identifies that while these shortcuts are beneficial to allow enough time to be able to
teach more complex examples, they do not always reinforce basic principles. Since the textbook does not
usually reinforce these principles in later chapters, the burden falls on the shoulders of the professor.
13
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
C. Resulting action plan:
Based on A and B, what changes, if any, do you anticipate making?
The results of the assessment will be disseminated to the three instructors who teach CH-251 so all
instructors can evaluate the students’ learning. Future discussions with the instructors will discuss the
outcome of each question and discuss strategies to improve student learning on key concepts. A new
assessment test will be given in future semesters. This test is written by the American Chemical Society
(ACS) and is a national, standardized assessment test. Similar questions/topics as above will be chosen on
the ACS test and the results on each test will be compared.
This assessment was useful in guiding our approach on future tests with four aspects in mind: 1) questions
should avoid ambiguity in the answer or in the way the question is written, 2) fewer parts should be asked
per question thereby simplifying the rubric, and 3) the students should have an incentive to study for the
test to be able to assess true end-of-year student learning and retention of key concepts.
Another potential strategy for a revised KPRS assessment exam is to increase the diversity of questions by
asking each organic chemistry instructor to provide two to three questions for each of the four main topics general chemistry concepts, resonance concepts, mechanism concepts, and chemical reactions. From this
pool of questions, the instructors could randomly select one question for each of the four main topics and
include them in the general test format.
14
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
KPRS Assessment Exam
CH-251 Questions for Assessment
1. In which structure(s) below, does sulfur have a formal charge of + 1?
a) S(CH 3 ) 3
b) H 2 S
c) SO 3
d) H 2 SO 4
2. Which of the following would have a trigonal planar structure?
a) CH 4
b) NH 3
c) BCl 3
3. Which of the following is a Lewis base?
a) BF 3
b) P(CH 3 ) 3
c) NH 4 +
d) PCl 3
d) H 3 O+
4. Fill in the information for each compound:
Molecule
Hybridization
Bond angle
Lewis structure
BeCl 2
HNO 3
5. Draw three resonance structures for azide, N 3 –. Make sure to include all bonds and lone pairs
and any formal charges. Which of these three is the least contributing structure and briefly
explain why?
6. Convert the Fischer projection seen below to a line angle formula with the correct
stereochemistry. Also, identify each chiral center as R or S.
CH2OH
Br
HO
CH3
H
CH2CH3
15
CH-251 Fall 2011 and Spring 2012 KPRS Course Assessment
Prepared by Julie Pigza and John Regan
7. Consider the monobromination (Br 2 , 1 mole/UV) of 2-methylbutane. Provide structures for
all isomers formed (include stereoisomers).
8. Give the stereochemical relationship between each of the pair of structures:
a) A and B _______________ b) B and C _______________ c) A and C _______________
H
Cl
H
Br
Cl
H
H
H
CH2CH3
CH3
Br
CH3
CH2CH3
A
B
H
Br
Cl
CH3
CH2CH3
C
9. Circle the meso compound(s) among the structures below:
a) cis-1,2-dimethylcyclohexane
c) trans-1,2-dimethylcyclohexane
b) cis-1,3-dimethylcyclohexane
d) trans-1,3-dimethylcyclohexane
10. Draw the mechanism, with arrow pushing, of the following S N 1 reaction.
Br
CH3OH
Δ
OCH3
11. Predict the product(s) for the following reactions:
H3C
CH3
I
CH3
H3C
I
NaOCH3
DMSO
CH3OH
16