CHEM200_OBTL_2014_2015 (1)

University of Santo TomasFaculty of Pharmacy

An Outcomes-Based Teaching-Learning Program for Organic Chemistry1st Semester, A.Y. 2014-2015

Course Title: Organic ChemistryCourse Number:CHEM 200Credit 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 semPrerequisite:CHEM 111 and CHEM 112 (for BS Biochemistry students)CHEM 100 (for BS Pharmacy and BS Medical Technology students)

Course Facilitators:Prof. Angelita S. Sarile, Ph.D.,Ms. Gladys M. Ilagan and Ms. Myla R. SantiagoCourse 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. Ma. Elena J. Manansala, MSc.Dean, Faculty of Pharmacy

Date of Approval:14 June 2014

INSTITUTIONAL INTENDED LEARNING OUTCOMEGRADUATE ATTRIBUTEPROGRAM INTENDED LEARNING OUTCOMECOURSE INTENDED LEARNING OUTCOME

Academic ExcellenceShow expertise in the competencies necessary to the practice of the professionDemonstrate creative application of concepts and methods of pharmacy practice geared towards the advancement of various fields and of Pharmacy1. Demonstrate ability to discuss the structure, properties, nomenclature, reactivity and reaction mechanisms of the different classes of organic compounds

Leadership and TeamworkDemonstrate capacity for leadership and teamwork including the ability to motivate others, to be responsible and reliableAssume leadership roles as appropriate, and work effectively and work harmoniously as members of healthcare teams2. 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 SkillsInitiate innovative ideas and methods through research responsive to the changing needs of the societyDemonstrate critical application of principles in pharmacy using logical and systematic methods to provide practical solutions to real-life professional situations3. Develop skills in communicating chemical information by way of designing simple syntheses and emphasizing the relationship between structure and reactivity

Productivity and AccountabilityDevelop new knowledge and understanding that will contribute to nation-building and sustainable development through the processes of inquiry, research and innovationGenerate insights and new knowledge in pharmacy that will contribute to nation-building and sustainable development through drug designs and development for the prevention, diagnosis, mitigation and treatment of diseases of man and animals4. 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 ResponsibilitiesHold 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 society5. 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

Communication and Relational SkillsDevelop effective communication competencies through interpersonal skills and utilize information technology responsibly as effective tool ion exploring and expressing ideasApply 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 relationship s by providing drug and health related information6. Enhance skills in web-based learning tools and other information technology resources.

Intended Learning Outcomes ContentTeaching-Learning ActivitiesAssessment Tasks

1. Describe the electronic structure of atoms CILO12. Differentiate ionic from covalent bonds CILO13. Exhibit initiative to lead and cooperate in performing assigned tasks and/or activities CILO 24. Practice social and ethical responsibilities in the use of facilities and resources CILO5

5. Calculate the formal charge of the atom CILO16. Describe the hybridization of atoms present in simple organic compounds CILO 67. Exhibit initiative to lead and cooperate in performing assigned tasks and/or activities CILO 28. Predict the direction of polarity of a bond CILO1

9. Identify functional groups in organic molecules CILO1Unit I: Covalent Bonding and Shapes of Molecules

1.1 Atomic structure; atomic orbitals

1.2 Electronegativity and chemical bonds1.2.1 Chemical Nature of Organic Compounds

1.3 Formal charge

1.4 Hybridization

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

Assigned reading

Work along activities

Lecture forum

Note taking

Information inquiry

Small group assignment

Scientific laboratory session

Cookbook laboratory work

Brain storming

Focused listing

Objective test

Lab practical

Analytic assessment

Critique paper

1. Discuss the different structural effects CILO32. Classify molecule as a Lewis acid or a Lewis base CILO13. Illustrate the effect of structure on pKa and the relationship between acidity and molecular structure CILO6

Unit II: Acids and Bases

2.1 Structural effects

2.2 Lewis acids and Lewis bases

2.3 Ka, pKa, Kb, pKb, pH

Interactive Lecturing

Work Along Exercises

Problem Sets

Problem Recognition Tasks

Analytic Assessment

1. Illustrate the different kinds of formulas CILO1

2. Differentiate all types of isomers CILO13. Classify the different types of carbon atoms CILO14. Discuss the properties and conformations of alkanes and cycloalkanes CILO 65. Exhibit initiative to lead and cooperate in performing assigned tasks and/or activities CILO 26. Practice social and ethical responsibilities in the use of facilities and resources CILO5Unit III: Alkanes and Cycloalkanes

3.1 Different kinds of formulas3.1.1 Chemical Formula-writing and Nomenclature of Organic Compounds3.2 Isomers3.3 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

Lecture Forum

Spontaneous Collaboration

Note taking

Information inquiry

Note taking

Information inquiry

Small group assignmentScientific laboratory session


Brain storming

Summarizing

Compare and contrast chart

Illustrating concepts and principles

Objective Test

1. Name and draw alkenes and cycloalkenes CILO12. Explain cis-trans isomers of alkenes CILO13. Assign E,Z configurations to double bonds CILO1

Unit IV: Alkenes and Alkynes4.1 Electronic structure of alkenes

4.2 Cis-trans isomers of alkenes

4.3 Sequence rules of E,Z designation

Assigned Reading


Problem Solving LearningProblem Sets

Problem Recognition Tasks

Documented Problem Solution

1. Classify organic reactions CILO12. Discuss the roles of radicals, nucleophiles and electrophiles in organic reactions CILO43. Formulate the mechanism of electrophilic addition reactions CILO34. Exhibit initiative to lead and cooperate in performing assigned tasks and/or activities CILO 25. Practice social and ethical responsibilities in the use of facilities and resources CILO56. Explain a reaction energy diagram CILO6

7. Predict the product of reactions of alkenes, dienes and alkynes CILO38. Demonstrate correct preparation of alkenes and alkynes CILO39. Describe the acidity of alkynes CILO110. Apply the principles of different reactions to determine the structure of an unknown compound CILO3

Unit V: Reactions of Alkenes and Alkynes

5.1 Kinds of organic reactions5.2 Organic reaction intermediates

5.3 Electrophilic addition reactions 5.3.1 Classification Tests for Hydrocarbons

5.4 Reaction energy diagrams and transition states5.5 Reactions of alkenes, dienes, and alkynes5.6 Preparation of alkenes and alkynes

5.7 Alkyne acidity 5.8 Structure elucidation

Gapped Lecture

Lecture Forum

Three-Minute Essay

Note taking

Information inquiry




Brain storming

Focused Listing

Whats the Principle

Analytic Assessment

Lab practical

Analytic assessment

Critique paper

1. Discuss chirality and optical activity CILO62. Locate stereocenters in molecules CILO13. Differentiate enantiomers from diastereomers; meso compounds from racemic mixture CILO34. Designate the configuration of a stereocenter CILO1Unit VI: Chirality: The Handedness of Molecules

6.1 Chirality and optical activity

6.2 Stereocenter 6.3 Enantiomers and diastereomers,meso compounds and racemic mixture6.4 R , S convention

Gapped Lecture

Lecture Forum

Three-Minute Essay

Problem Solving Learning

Focused Listing

Whats the Principle

Analytic Assessment


1. Illustrate the mechanisms of SN1 and SN2 reactions CILO3 2. Differentiate SN1 from SN2 reactions CILO3 3. Exhibit initiative to lead and cooperate in performing assigned tasks and/or activities CILO 24. Practice social and ethical responsibilities in the use of facilities and resources CILO55. Describe elimination reactions: E1 and E2 CILO16. Identify reactions as SN1, SN2, E1, and E2 CILO17. Predict the products of reactions of alkyl halides and the effects of changes in reaction conditions on substitution and elimination reactions CILO3 Unit VII: Haloalkanes

7.1 Mechanisms of SN2 and SN1 Reactions7.2 Comparison of SN2 and SN1 Reactions 7.2.1 Classification Tests for Organic Halides

7.3 Elimination reactions: E1 and E2 7.4 Competition between substitution and elimination 7.5 Factors affecting substitution and elimination

Interactive Lecturing

Work Along Activities

Note taking

Information inquiry




Brain storming

Problem Sets


Analytic Assessment

Objective test

Lab practical

Critique paper

1. Differentiate alcohols from phenols; ethers from epoxides; and thiols from sulfides CILO12. Exhibit initiative to lead and cooperate in performing assigned tasks and/or activities CILO 23. Practice social and ethical responsibilities in the use of facilities and resources CILO54. Compare the physical and chemical properties of alcohols, phenols, and ethers CILO3

5. Discuss synthesis alcohols, ethers, and phenols CILO36. Predict the products of reactions involving alcohols, phenols, and ethers CILO3Unit VIII: Alcohols, Ethers, and Thiols

8.1 Alcohols, phenols, ethers, epoxides, thiols, and sulfides

8.1.1 Classification Tests for Hydroxyl Compounds

8.2 Properties of alcohols, ethers and phenols: H-bonding, acidity 8.2.1 Simple and Fractional Distillation8.3 Synthesis of alcohols, phenols, and ethers8.4 Reactions of alcohols, phenols, and ethers

Lecture Forum

Assigned Reading

Workshop

Note taking

Information inquiry




Brain storming

Summarizing

Analytic Assessment

Objective test

Lab practical

Analytic assessment

Critique paper

.

1. Determine whether a substance is aromatic or antiaromatic CILO12. Formulate the mechanisms of electrophilic aromatic substitution reactions CILO33. Predict the reactivity and orientation of the aromatic ring and substituents in electrophilic aromatic substitution reactions CILO34. Discuss aromaticity in nonbenzene rings and polycyclic compounds CILO35. Outline the synthesis of substituted benzene through various reaction pathways CILO4Unit IX: Benzene and Its Derivatives

9.1 Benzene structure and stability9.2 Aromaticity and Antiaromaticity9.3 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

Lecture Forum


Web-Enhanced Activity

Summarizing

Analytic Assessment

Online Assessment

1. Differentiate 1o, 2o, 3o, and 4o amines CILO12. Exhibit initiative to lead and cooperate in performing assigned tasks and/or activities CILO 23. Practice social and ethical responsibilities in the use of facilities and resources CILO54. Evaluate the base strength of amines CILO35. Discuss the reactions and synthesis of amines CILO3

Unit X: Amines

10.1 Different types of amines 10.1.1 Classification Test for Amines

10.2 Basicity of amines

10.3 Reactions and synthesis of amines

Gapped Lecture

Lecture Forum

Three-Minute Essay

Note taking

Information inquiry




Brain storming

Focused Listing

Whats the Principle

Analytic Assessment

Objective test

Lab practical

Critique paper

1. Compare the reactivities of aldehydes with that of ketones CILO32. Discuss the different reactions of aldehydes and ketones CILO43. Exhibit initiative to lead and cooperate in performing assigned tasks and/or activities CILO 24. Practice social and ethical responsibilities in the use of facilities and resources CILO5

Unit XII: Aldehydes and Ketones

12.1 Electronic structure of carbonyl group12.2 Reactions of aldehydes and ketones 12.2.1 Classification Tests for Carbonyl Containing Compounds

Lecture Forum

Reflective Lecturing

information inquiry




Brain storming

Summarizing

Problem Sets

Objective test

Lab practical

Analytic assessment

Critique paper

1. Name and draw structural formulas for carboxylic acids CILO12. Compare acidity of carboxylic acids CILO33. Outline the necessary steps for the syntheses of various drugs CILO44. Exhibit initiative to lead and cooperatein performing assigned tasks and/or activities CILO 25. Practice social and ethical responsibilities in the use of facilities and resources CILO5

Unit XIII Carboxylic Acids

13.1 Nomenclature and structure of carboxylic acids13.2 Acidity of carboxylic acids13.3 Chemical transformations and syntheses 13.1.1 Synthesis of Aspirin


Assigned Reading

Lecture forum

Note taking

Information inquiry




Brain storming

Summarizing

Analytic Assessment

Objective test

Lab practical

Critique paper

1. Identify the functional derivatives of carboxylic acids CILO1

2. Discuss the physical and chemical properties of acid derivatives CILO13. Compare reactivities of carboxylic acid derivatives CILO34. Exhibit initiative to lead and cooperate in performing assigned tasks and/or activities CILO 25. Practice social and ethical responsibilities in the use of facilities and resources CILO56. Formulate mechanisms of simple nucleophilic acyl substitution reactions CILO6Unit XIV: Functional Derivatives of Carboxylic Acids

14.1 Nomenclature and structures of carboxylic acid derivatives

14.2 Properties of acid derivatives

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

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


Assigned Reading

Lecture forum

Note taking

Information inquiry




Brain storming

Web-Enhanced Activity

Summarizing

Analytic Assessment

Objective test

Lab practical

Critique paper

Online Assessment

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 LearningKlein, 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.LECTURELABORATORY

PrelimsFinals

Departmental Examination50%30%30%

Quizzes40%30%20%

Class Standing (Attendance/Performance/ Conduct)10%10%10%

Formal Reports---------15%15%

Pre-lab Assignment---------5%5%

Data Sheet---------5%5%

Post-lab Assignment---------5%5%

Practical Exam------------------10

TOTAL100%100%100%

COURSE POLICY: At least with an 80% attendance Passing rate: 75%

Prepared by:Prof. Angelita S. Sarile, Ph.D.

Reviewed by:Asst. Prof. Andrea G. Vargas, Chair, Department of Biochemistry

Approved by:Assoc. Prof. Ma. Elena J. Manansala, MSc.Dean, Faculty of Pharmacy

Date of Approval:14 June 2014

TENTATIVE COURSE CALENDAR:

WEEKCONTENT

1Covalent Bonding; Acids and Bases

2Alkanes and Cycloalkanes

3Reactions of Alkenes and Alkynes

4

5Benzene and its Derivatives

6MONTHLY

7Haloalkanes

8

9Chirality

10Alcohols, Thiols, and Ethers

11

12PRELIMS

13Aldehydes and Ketones

14

15Carboxylic Acids

16Carboxylic Acid Derivatives

17

18FINALS

Introduction to Organic Chemistry5th ed. Brown, W. and Poon, T.EXERCISES

Unit I

1.171.22 1.251.27 d, f, i, l,o1.331.371.511.551.64Unit III

3.143.203.263.333.363.49PIT # 10 and 11

Unit V

5.135.165.195.285.325.465.51Unit VII

7.11 b,d,f7.22 b,d,f7.26 a,c,e7.35 b,c,d7.367.437.44 a,d,g7.46

Unit IX

9.11 b,d,f,h9.239.26 f,g,h,i,j9.289.319.369.419.47

Unit XII

12.1312.14 d,f,g,h12.2112.40 a,b,c12.44 Unit XIV

14.1514.2114.2914.4514.46 f,g,h

Unit II

2.102.172.192.282.292.362.39Unit IV

4.124.18 a,c,e4.19 b,c,d4.21 b,d,f4.22 a,c,e4.274.36Unit VI

6.136.226.24PIT # 6,7 and 14Unit VIII

8.13 b,d,e,h8.15 a,c,e8.24 8.258.298.388.428.47

Unit X

10.1210.1410.1510.2210.3610.43Unit XIII

13.1713.3013.3213.3913.46

CHEM200_OBTL_2014_2015 (1)

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