University of Santo Tomas

Faculty of Pharmacy
An Outcomes-Based Teaching-Learning Program for Organic Chemistry
1st Term, A.Y. 2015-2016
Course Title:

Organic Chemistry

Course Number:

CHEM 200

Credit Units::

5 units (3 units lecture and 2 units laboratory)

Contact Hours:

3 lecture hours and 6 laboratory hours per week

Course Placement:

2nd year, 1st term

Prerequisite:

CHEM 111 and CHEM 112 (for BS Biochemistry students)

CHEM 100 (for BS Pharmacy and BS Medical Technology students)

Course Facilitators:

Gladys I. Bathan, Aristea V. Bayquen, Stephanie L. Chua, Angelica C. Crisostomo, Regine Philline S. del Rosario,
Regine Camille V. Gonzales, Leonardo A. Guevarra Jr., Ma. Irene D. Liu, Clemone John S. Madarang , Angelita S. Sarile,
Myla R. Santiago, Peter C. Torres

Course Description:

The course deals with the different classes of organic compounds, their structures, properties, reactivities, reaction
mechanisms, and applications to different biochemical and health-related fields of study. It includes training in both
classical and modern semi-micro laboratory techniques in handling, preparing, separating, purifying, identifying and
characterizing organic compounds.

Prepared by:

Prof. Angelita S. Sarile, Ph.D.

Reviewed by:

Asst. Prof. Andrea G. Vargas,

Chair, Department of Biochemistry

Approved by:

Assoc. Prof. Jocelyn D. Domingo

Acting Dean

Date of Approval:

30 July 2015

INSTITUTIONAL INTENDED LEARNING OUTCOME

GRADUATE ATTRIBUTE
Academic Excellence
Show expertise in the competencies necessary to the
practice of the profession

PROGRAM INTENDED LEARNING

OUTCOME

COURSE INTENDED LEARNING OUTCOME

Demonstrate creative application of concepts

and methods of pharmacy practice geared
towards the advancement of various fields and
of Pharmacy

1.

Demonstrate ability to discuss the structure,

properties, nomenclature, reactivity and
reaction mechanisms of the different classes of
organic compounds

Leadership and Teamwork

Demonstrate capacity for leadership and teamwork
including the ability to motivate others, to be
responsible and reliable

Assume leadership roles as appropriate, and

work effectively and work harmoniously as
members of healthcare teams

2.

Exhibit leadership roles in illustrating the

relevance and applications of the reactions and
interactions of organic molecules to the world
around us, particularly to the biochemical,
health and biological sciences

Critical Thinking and Problem-Solving Skills

Initiate innovative ideas and methods through
research responsive to the changing needs of the
society
Productivity and Accountability
Develop new knowledge and understanding that will
contribute to nation-building and sustainable
development through the processes of inquiry,
research and innovation

Demonstrate critical application of principles

in pharmacy using logical and systematic
methods to provide practical solutions to reallife professional situations

3.

Develop skills in communicating chemical

information by way of designing simple
syntheses and emphasizing the relationship
between structure and reactivity

Generate insights and new knowledge in

pharmacy that will contribute to nationbuilding and sustainable development through
drug designs and development for the
prevention, diagnosis, mitigation and
treatment of diseases of man and animals

4.

Explore the interrelation between mechanistic

understanding of organic reactions and
practical applications to drug design and
development, health care, energy and the
environment

Social and Ethical Responsibilities

Hold Catholic values and moral principles reflective of
the competent, committed and compassionate
Thomasian in the formation of humanely progressive
and healthy society

Exhibit Catholic values and moral principles

reflective of the Thomasian identity;
competent, committed and compassionate, as
health care professionals in the formation of
humanely progressive and healthy society

5.

Communication and Relational Skills

Develop effective communication competencies
through interpersonal skills and utilize information
technology responsibly as effective tool in exploring
and expressing ideas

Apply effective communication competencies

through interpersonal skills and utilize
information technology responsibly as an
effective tool in exploring and expressing ideas
individually and collaboratively and in
maintaining therapeutic relationships by
providing drug and health related information

6.

Manifest Catholic values and moral principles

by developing the skills necessary to generate
less hazardous waste in the laboratory and by
learning to protect the environment by the
proper disposal or recycling of all reagents and
end products
Enhance skills in web-based learning tools and
other information technology resources.

Intended Learning Outcomes

1. Describe the electronic structure

of atoms CILO1
2. Differentiate ionic from covalent
bonds CILO1
3. Exhibit initiative to lead and
cooperate in performing assigned
tasks and/or activities CILO 2
4. Practice social and ethical
responsibilities in the use of
facilities and resources CILO5

Content
Unit I: Covalent Bonding and Shapes
of Molecules
1.1 Atomic structure; atomic orbitals

Teaching-Learning Activities

Assigned reading

1.2 Electronegativity and chemical

Work along activities
bonds
1.2.1 Chemical Nature of Organic Lecture forum
Compounds
Note taking
Information inquiry
Small group assignment

5. Calculate the formal charge of the

atom CILO1
6. Describe the hybridization of
atoms present in simple organic
compounds CILO 6
7. Exhibit initiative to lead and
cooperate in performing assigned
tasks and/or activities CILO 2
8. Predict the direction of polarity of
a bond CILO1

9. Identify functional groups in

organic molecules CILO1

1.3 Formal charge

Scientific laboratory session
1.4 Hybridization
Cookbook laboratory work
1.4.1 Molecular Modeling of
Organic Compounds

1.5 Bond polarity

1.5.1 Extraction
1.5.2 Column and Thin layer
Chromatography
1.6 Functional groups
1.6.1 Comparative Investigation
of Organic Compounds

Brain storming

Assessment Tasks

Focused listing
Objective test
Lab practical
Analytic assessment
Critique paper

Intended Learning Outcomes

1.

Discuss the different structural effects

Content
Unit II: Acids and Bases

Teaching-Learning Activities

Assessment Tasks

2.1 Structural effects

Interactive Lecturing

Problem Sets

2.2 Lewis acids and Lewis bases

Work Along Exercises

Problem Recognition Tasks

CILO3

2. Classify molecule as a Lewis acid or a

Lewis base CILO1
3. Illustrate the effect of structure on pKa
and the relationship between acidity
and molecular structure CILO6

2.3 Ka, pKa, Kb, pKb, pH

Analytic Assessment

Unit III: Alkanes and Cycloalkanes

1. Illustrate the different kinds of
formulas CILO1

2. Differentiate all types of isomers CILO1

3. Classify the different types of carbon
atoms CILO1
4. Discuss the properties and
conformations of alkanes and
cycloalkanes CILO 6
5. Exhibit initiative to lead and cooperate
in performing assigned tasks and/or
activities CILO 2
6. Practice social and ethical
responsibilities in the use of facilities
and resources CILO5

3.1 Different kinds of formulas

3.1.1 Chemical Formula-writing
and Nomenclature of Organic
Compounds
3.2 Isomers
3.3 Types of carbon atoms
3.4 Boiling/melting points; solubility;
Conformations of alkanes and
cycloalkanes
3.4.5 Sublimation and Melting point
Determination

Gapped Lecture

Summarizing

Lecture Forum

Compare and contrast chart

Spontaneous Collaboration

Illustrating concepts and

principles

Note taking
Objective Test
Information inquiry
Note taking
Information inquiry
Small group assignment
Scientific laboratory session
Cookbook laboratory work
Brain storming

Unit IV: Alkenes and Alkynes

1. Name and draw alkenes and

4.1 Electronic structure of alkenes

Assigned Reading

Problem Sets

Intended Learning Outcomes

cycloalkenes CILO1
2. Explain cis-trans isomers of alkenes
CILO1

Content
4.2 Cis-trans isomers of alkenes

Teaching-Learning Activities
Work Along Exercises

Assessment Tasks
Problem Recognition Tasks

4.3 Sequence rules of E,Z designation

Problem Solving Learning

Documented Problem
Solution

Gapped Lecture

Focused Listing

Lecture Forum

Whats the Principle

Three-Minute Essay

Analytic Assessment

Note taking

Lab practical

Information inquiry

Analytic assessment

Small group assignment

Critique paper

3. Assign E,Z configurations to double

bonds CILO1
Unit V: Reactions of Alkenes and
Alkynes
1. Classify organic reactions CILO1
2. Discuss the roles of radicals,
nucleophiles and electrophiles in
organic reactions CILO4
3. Formulate the mechanism of
electrophilic addition reactions CILO3
4. Exhibit initiative to lead and cooperate
in performing assigned tasks and/or
activities CILO 2
5. Practice social and ethical
responsibilities in the use of facilities
and resources CILO5
6. Explain a reaction energy diagram CILO6
7. Predict the product of reactions of
alkenes, dienes and alkynes CILO3
8. Demonstrate correct preparation of
alkenes and alkynes CILO3
9. Describe the acidity of alkynes CILO1
10. Apply the principles of different
reactions to determine the structure of an
unknown compound CILO3

5.1 Kinds of organic reactions

5.2 Organic reaction intermediates

5.3 Electrophilic addition reactions

5.3.1 Classification Tests for
Hydrocarbons

Scientific laboratory session

5.4 Reaction energy diagrams and
transition states
5.5 Reactions of alkenes, dienes, and
alkynes
5.6 Preparation of alkenes and alkynes
5.7 Alkyne acidity
5.8 Structure elucidation

Cookbook laboratory work

Brain storming

Intended Learning Outcomes

1.

Discuss chirality and optical activity

Content
Unit VI: Chirality: The Handedness of
Molecules

Teaching-Learning Activities

Assessment Tasks

6.1 Chirality and optical activity

Gapped Lecture

Focused Listing

6.2 Stereocenter
6.3 Enantiomers and diastereomers,
meso compounds and racemic
mixture
6.4 R , S convention

Lecture Forum

Whats the Principle

Three-Minute Essay

Analytic Assessment

Problem Solving Learning

Documented Problem
Solution

Interactive Lecturing

Problem Sets

Work Along Activities

Documented Problem
Solution

CILO6

2. Locate stereocenters in molecules CILO1

3. Differentiate enantiomers from
diastereomers; meso compounds from
racemic mixture CILO3
4. Designate the configuration of a
stereocenter CILO1

Unit VII: Haloalkanes

1. Illustrate the mechanisms of SN1 and
SN2 reactions CILO3
2. Differentiate SN1 from SN2 reactions
CILO3

7.1 Mechanisms of SN2 and SN1

Reactions
7.2 Comparison of SN2 and SN1
Reactions
7.2.1 Classification Tests for
Organic Halides

3. Exhibit initiative to lead and cooperate

in performing assigned tasks and/or
activities CILO 2
4. Practice social and ethical
responsibilities in the use of facilities
and resources CILO5
5. Describe elimination reactions: E1 and 7.3 Elimination reactions: E1 and E2
E2 CILO1
6. Identify reactions as SN1, SN2, E1, and
7.4 Competition between substitution
E2 CILO1
and elimination
7. Predict the products of reactions of
7.5 Factors affecting substitution and
alkyl halides and the effects of changes
elimination
in reaction conditions on substitution
and elimination reactions CILO3

Note taking
Analytic Assessment
Information inquiry
Objective test
Small group assignment
Lab practical
Scientific laboratory session
Critique paper
Cookbook laboratory work
Brain storming

Intended Learning Outcomes

1. Differentiate alcohols from phenols;

ethers from epoxides; and thiols from
sulfides CILO1
2. Exhibit initiative to lead and cooperate
in performing assigned tasks and/or
activities CILO 2
3. Practice social and ethical
responsibilities in the use of facilities
and resources CILO5
4. Compare the physical and chemical
properties of alcohols, phenols, and
ethers CILO3
5. Discuss synthesis alcohols, ethers, and
phenols CILO3
6. Predict the products of reactions
involving alcohols, phenols, and ethers

Content
Unit VIII: Alcohols, Ethers, and Thiols
8.1 Alcohols, phenols, ethers,
epoxides, thiols, and sulfides

Teaching-Learning Activities

Assessment Tasks

Lecture Forum
Summarizing

8.1.1 Classification Tests for

Hydroxyl Compounds

Assigned Reading
Analytic Assessment
Workshop
Objective test
Note taking
Lab practical

8.2 Properties of alcohols, ethers and

phenols: H-bonding, acidity
8.2.1 Simple and Fractional
Distillation
8.3 Synthesis of alcohols, phenols,
and ethers
8.4 Reactions of alcohols, phenols,
and ethers

CILO3

Information inquiry
Analytic assessment
Small group assignment
Critique paper
Scientific laboratory session
Cookbook laboratory work
Brain storming

Unit IX: Benzene and Its Derivatives

1. Determine whether a substance is

aromatic or antiaromatic CILO1
2. Formulate the mechanisms of
electrophilic aromatic substitution
reactions CILO3
3. Predict the reactivity and orientation
of the aromatic ring and substituents
in electrophilic aromatic substitution
reactions CILO3
4. Discuss aromaticity in nonbenzene
rings and polycyclic compounds CILO3
5. Outline the synthesis of substituted
benzene through various reaction
pathways CILO4

9.1 Benzene structure and stability

9.2 Aromaticity and Antiaromaticity
9.3 Electrophilic aromatic substitution
reactions of benzene
9.4 Substituent effects in electrophilic
aromatic substitutions

9.5 Polycyclic aromatic compounds

9.6 Organic synthesis

Gapped Lecture

Summarizing

Lecture Forum

Analytic Assessment

Work Along Exercises

Online Assessment

Web-Enhanced Activity

Intended Learning Outcomes

Content

Teaching-Learning Activities

Assessment Tasks

Unit X: Amines
1. Differentiate 1o, 2o, 3o, and 4o amines
CILO1

2. Exhibit initiative to lead and cooperate

in performing assigned tasks and/or
activities CILO 2
3. Practice social and ethical
responsibilities in the use of facilities
and resources CILO5
4. Evaluate the base strength of amines

10.1 Different types of amines

Gapped Lecture
10.1.1 Classification Test for Amines
Lecture Forum

Focused Listing
Whats the Principle

Three-Minute Essay

Analytic Assessment

Note taking

Objective test

10.2 Basicity of amines

Information inquiry

Lab practical

10.3 Reactions and synthesis of

amines

Small group assignment

Critique paper

CILO3

5. Discuss the reactions and synthesis of

amines CILO3

Scientific laboratory session

Cookbook laboratory work
Brain storming
Unit XII: Aldehydes and Ketones
1. Compare the reactivities of aldehydes
with that of ketones CILO3
2. Discuss the different reactions of
aldehydes and ketones CILO4
3. Exhibit initiative to lead and cooperate
in performing assigned tasks and/or
activities CILO 2
4. Practice social and ethical
responsibilities in the use of facilities
and resources CILO5

12.1 Electronic structure of carbonyl

group
12.2 Reactions of aldehydes and
ketones
12.2.1 Classification Tests for
Carbonyl Containing
Compounds

Lecture Forum

Summarizing

Reflective Lecturing

Problem Sets

information inquiry

Objective test

Small group assignment

Lab practical

Scientific laboratory session

Analytic assessment

Cookbook laboratory work

Critique paper

Brain storming

Intended Learning Outcomes

1. Name and draw structural formulas for

carboxylic acids CILO1
2. Compare acidity of carboxylic acids CILO3
3. Outline the necessary steps for the
syntheses of various drugs CILO4
4. Exhibit initiative to lead and cooperate
in performing assigned tasks and/or
activities CILO 2
5. Practice social and ethical
responsibilities in the use of facilities
and resources CILO5

Content
Unit XIII Carboxylic Acids

Teaching-Learning Activities

Assessment Tasks

13.1 Nomenclature and structure of

carboxylic acids
13.2 Acidity of carboxylic acids
13.3 Chemical transformations and
syntheses
13.1.1 Synthesis of Aspirin

Problem Solving Learning

Summarizing

Assigned Reading

Analytic Assessment

Lecture forum

Objective test

Note taking

Lab practical

Information inquiry

Critique paper

Small group assignment

Scientific laboratory session
Cookbook laboratory work
Brain storming
Unit XIV: Functional Derivatives of
Carboxylic Acids

1. Identify the functional derivatives of

carboxylic acids CILO1

14.1 Nomenclature and structures of

carboxylic acid derivatives

2. Discuss the physical and chemical

properties of acid derivatives CILO1
3. Compare reactivities of carboxylic acid
derivatives CILO3
4. Exhibit initiative to lead and cooperate
in performing assigned tasks and/or
activities CILO 2
5. Practice social and ethical
responsibilities in the use of facilities
and resources CILO5

14.2 Properties of acid derivatives

14.3 Reactivities of carboxylic acid
derivatives
14.3.1 Synthesis of Soap and
Detergent

Problem Solving Learning

Summarizing

Assigned Reading

Analytic Assessment

Lecture forum

Objective test

Note taking

Lab practical

Information inquiry

Critique paper

Small group assignment

Online Assessment

Scientific laboratory session

Intended Learning Outcomes

6. Formulate mechanisms of simple
nucleophilic acyl substitution reactions
CILO6

Content
14.4 Characteristic reactions of
carboxylic acid derivatives
14.4.1 Classification Tests for
Carboxylic Acids and
Derivatives

Teaching-Learning Activities

Assessment Tasks

Cookbook laboratory work

Brain storming
Web-Enhanced Activity

REFERENCES:
Bathan, G.I., Bayquen, A.V., Crisostomo, A.B.C., Cruz, C.T., de Guia, R.M., Farrow, F.L., Pea, G.T., Sarile,A.S. and Torres, P.C. (eds.) (2014).
Laboratory Manual in Organic Chemistry. Quezon City,Philippines: C & E Publishing, Inc.
Brown, W. H. and Poon, T. (2014). Introduction to Organic Chemistry. 5th ed. New Jersey: John Wiley & Sons, Inc.
Hart H., Craine LE, Hart DJ, and Hadad CM. (2012). Organic Chemistry A Brief Course. 13th ed. Brooks/Cole, CENGAGE Learning
Klein, David R. (2012) Organic Chemistry New Jersey: John Wiley & Sons, Inc.
Lim-Sylianco, Clara Y. Principles of Organic Chemistry. 6th ed. Aurum Technical Books.
McMurry J. (2011). Fundamentals of Organic Chemistry. 7th ed. Thomson Brooks/Cole, Belmont, CA, USA.
Solomons, T.W. G., Fryhle, C.B., Snyder, S.A. (2014). Organic Chemistry. 11th ed. John Wiley and Sons, Inc., New York.

GRADING SYSTEM:
The overall grade is composed of 20% monthly grade, 40% preliminary grade and 40% final grade. The preliminary and final grades consist of 60% lecture
and 40% laboratory. The lecture and laboratory grades are computed as follows.
LECTURE
Departmental Examination
Quizzes
Class Standing (Attendance/Performance/ Conduct)
Formal Reports
Pre-lab Assignment
Data Sheet
Post-lab Assignment
Practical Exam
TOTAL

50%
40%
10%
----------------------------------------100%

LABORATORY
Prelims
Finals
30%
30%
30%
20%
10%
10%
15%
15%
5%
5%
5%
5%
5%
5%
--------10
100%
100%

COURSE POLICY: At least with an 80% attendance

Passing grade: Raw score of 60%

TENTATIVE COURSE CALENDAR:

WEEK
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18

CONTENT
Covalent Bonding; Acids and Bases
Alkanes and Cycloalkanes
Reactions of Alkenes and Alkynes
Benzene and its Derivatives
FIRST GRADING PERIOD
Haloalkanes
Chirality
Alcohols, Thiols, and Ethers
SECOND GRADING PERIOD
Aldehydes and Ketones
Carboxylic Acids
Carboxylic Acid Derivatives
THIRD GRADING PERIOD

Introduction to Organic Chemistry

5th ed. Brown, W. and Poon, T.

EXERCISES 2015-2016
Unit I

Unit III

Unit V

Unit VII

Unit IX

Unit XII

Unit XIV

1.17
1.22
1.26
1.27 e,f,g,h
1.33
1.38 a,c,e,g
1.51
1.54 b,d,e
1.64

3.14
3.20
3.26
3.33
3.36
3.49
PIT # 10 and 11

5.13
5.15
5.19
5.28
5.31
5.47
5.51

7.12
7.21
7.26 a,c,e
7.35 b,c,d
7.43
7.44 a,d,g
7.46

9.11 b,d,f,h
9.23
9.26 f,g,h,i,j
9.28
9.31
9.36
9.41
9.47

12.13
12.14 d,f,g,h
12.21
12.22
12.40
12.44

14.15
14.21
14.29
14.45
14.46 f,g,h

Unit II

Unit IV

Unit VI

Unit VIII

Unit X

Unit XIII

2.10
2.17
2.19
2.28
2.29
2.36
2.39

4.13
4.19
4.22
4.27
4.36

6.13
6.22
6.24
PIT # 6,7 and 15

8.13 b,d,e,h
8.18
8.24
8.30
8.38
8.42
8.48

10.12
10.14
10.15
10.22
10.36
10.43

13.17
13.30
13.32
13.39
13.46