CHEM 200 - Organic Chemistry (Laboratory)

UNIVERSITY OF SANTO TOMAS FACULTY OF PHARMACY A Syllabus for Organic Chemistry Laboratory First Semester AY 2012-2013 Course Title:

ORGANIC CHEMISTRY LABORATORY

Course Number:

Chem 200

Course Description:

This one-semester course introduces students to both classical and modern semi-micro laboratory techniques used in organic chemistry. It emphasizes learning fundamental techniques and procedures for handling, preparing, separating, purifying, identifying and characterizing organic compounds. Students are expected to demonstrate their knowledge and understanding of the core concepts and principles of organic chemistry learned in the various laboratory experiments.

Course Credit:

2 units

Contact Hours:

6 hours per week

Prerequisite:

General Inorganic Chemistry (CHEM 100)

Placement:

Second Year, First Semester

General Objectives: 1. 2. 3. 4. 5. 6.

Handle organic chemicals in the laboratory. Determine purity of organic compounds using suitable techniques and methods. Characterize certain organic compounds using appropriate techniques and methods. Analyze organic compounds using chemical tests based on functional groups. Relate practical applications of organic chemistry to daily activities. Write formal reports using a scientific journal type format.

ACTIVITIES, EXPERIMENTS AND SPECIFIC OBJECTIVES Activity 1: General orientation on the following: syllabus, laboratory rules and regulations, safety and first aid, standard operating procedure in doing experiments, writing formal report, grading system, and grouping

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Activity 2: Distribution of apparatus; review of basic calculations: % yield and significant figures; classification of organic compounds based on their functional group; IUPAC nomenclature and formula-writing and molecular modeling for organic compounds FIRST GRADING PERIOD Experiments on Physical Methods of Analysis

Specific Objectives

Topic

Time allotted (hrs)

Teaching Strategies

Skills

Values

Experiment 1 Simple and Fractional Distillation 1. differentiate simple from fractional distillation 2. separate components of an alcoholic beverage 3. calculate the percentage of ethanol in the alcoholic beverages

• process of simple and fractional distillation

1. compare single and multiple extraction of caffeine from dried tea leaves 2. calculate the percentage yield of caffeine for both extraction procedures

• extracting caffeine from dried tea leaves

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• pre-lab and post-lab discussions

Mathematical skill Differentiation Analytical

Accuracy Innovativeness Cleanliness Logical thinking Efficiency

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• pre-lab and post-lab discussions

Mathematical Skill Differentiation Analytical

Accuracy Innovativeness Cleanliness Logical thinking Efficiency

• determining % alcohol in alcoholic beverages Experiment 2 Extraction

• comparing % yield of caffeine using single and multiple extraction Experiment 3 Sublimation and Melting Point Determination

1. purify benzoic acid by sublimation 2. determine and compare melting point of the product with a standard 3. calculate the percentage recovery

• purifying by sublimation and deposition • determining melting point • computing the percentage

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• pre-lab and post-lab discussions

Mathematical Skill Differentiation Analytical

Accuracy Innovativeness Cleanliness Logical thinking

Evaluation/ Assessment

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

• quizzes • pre-lab and post-lab assignments • data sheet • formal

2

recovery

Efficiency

report

Experiment 4 Recrytallization 1. synthesize acetanilide by acetylation of aniline 2. purify crude acetanilide product by recrystallization

• synthesizing acetanilide from aniline • purifying crude acetanilide

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• pre-lab and post-lab discussions

Mathematical Skill Differentiation Analytical

Accuracy Innovativeness Cleanliness Logical thinking Efficiency

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

6

• pre-lab and post-lab discussions

Mathematical Skill Differentiation Analytical

Accuracy Innovativeness Cleanliness Logical thinking Efficiency

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

Experiment 5 Column and Thin Layer Chromatography 1. separate the colored components of siling labuyo and malunggay leaves using column chromatography 2. predict the purity of components using thin layer chromatography (TLC) 3. measure the Rf values of the colored components in TLC

• using column chromatography to separate colored components of leaves • interpreting the composition of the leaf samples based on experimental results • relating Rf values to the chemical nature of the components

3 hrs. lab

PRELIMINARY EXAMINATION

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SECOND GRADING PERIOD Experiments on Analysis of Organic Compounds

Specific Objectives

Topic

Time allotted (hrs)

Teaching Strategies

Skills

Values

Evaluation/ Assessment

Experiment 6 Comparative Investigation of Organic Compounds differentiate organic compounds in terms of a. certain intrinsic physical properties b. behavior towards ignition c. IR spectra of their functional groups

• identifying and characterizing different functional groups using solubilities in H2O, HCl and NaOH, ignition results and infrared (IR) spectra

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• pre-lab and post-lab discussions

Differentiation Critical thinking Analytical

Innovativeness Cleanliness Logical thinking Systematic working Efficiency

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

4

• pre-lab and post-lab discussions

Differentiation Critical thinking Analytical

Innovativeness Cleanliness Logical thinking Systematic working Efficiency

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

Experiment 7 Classification Tests for Hydrocarbons differentiate hydrocarbons in terms of a. intrinsic physical properties b. chemical properties in terms of structure and behavior

• classifying hydrocarbons by observing chemical and physical properties, chemical tests and reactions, ignition (or flammability) test, Baeyer’s and Bromine tests nitration and oxidation with KMnO4

Analysis of Unknown 1: Hydrocarbons

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4

Experiment 8 Classification Tests for Organic Halides 1. differentiate primary, secondary and tertiary organic halides based on their SN reactivity 2. differentiate using equations SN1 from SN2 mechanisms with organic halides

• classifying organic halides according to their SN1 and SN2 reactivity • performing specific differentiating tests: Beilstein test and reaction with alcoholic AgNO3 and NaI in acetone Experiment 9 Classification Tests for Carbonyl and Hydroxyl Compounds

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• pre-lab and post-lab discussions

Differentiation Critical thinking Analytical

Innovativeness Cleanliness Logical thinking Systematic working Efficiency

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

1. distinguish whether a compound in hydroxyl- or carbonylcontaining 2. differentiate the three types of alcohols 3. differentiate aldehydes from ketones 4. explain using the mechanisms in the differentiating tests

•using the reaction mechanisms involved in the differentiating tests for the hydroxyl and carbonylcontaining compounds: Lucas test, chromic acid test, 2, 4-DNPH test, Tollens’ test, and Fehling’s test

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• pre-lab and post-lab discussions

Differentiation Critical thinking Analytical

Innovativeness Cleanliness Logical thinking Systematic working Efficiency

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

Analysis of Unknown 2: Oxygen-containing Compounds

3

5

Experiment 10 Classification Tests for Carboxylic Acids and Derivatives 1. differentiate reactivity of carboxylic acid derivatives 2. differentiate carboxylic acid derivatives using chemical tests 3. explain using chemical equations and mechanisms the reactions involved in each test

• examining differences in the reactivity of acid derivatives using chemical reactions like: hydrolysis, Schotten-Baumann reaction, aminolysis (anilide formation), and hydroxamic acid test

3

• pre-lab and post-lab discussions

Differentiation Critical thinking Analytical

Innovativeness Cleanliness Logical thinking Systematic working Efficiency

3

• pre-lab and post-lab discussions

Differentiation Critical thinking Analytical

Innovativeness Cleanliness Logical thinking Systematic working Efficiency

2

• pre-lab and post-lab discussions

Mathematical Skill Differentiation Analytical

Accuracy Innovativeness Cleanliness Logical thinking Efficiency

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

Experiment 11 Classification Tests for Amines 1. differentiate primary, secondary, and tertiary amines using Hinsberg test 2. explain using chemical equations and mechanisms involved in the test

• employing Hinsberg test to differentiate primary, secondary and tertiary amines

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

Experiment 12 Synthesis of Aspirin 1. explore the chemical process in the synthesis of aspirin 2. calculate the percentage yield of aspirin

• preparing aspirin • computing for the percentage yield of aspirin

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

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Experiment 13 Synthesis of Soap and Detergent 1. synthesize soap and detergent 2. compare the behavior of soap and detergent in hard water

• comparing soap with detergent as to mode of synthesis and behavior in hard water

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3 hrs. lab

• pre-lab and post-lab discussions

Mathematical Skill Differentiation Analytical

Accuracy Innovativeness Cleanliness Logical thinking Efficiency

• quizzes • pre-lab and post-lab assignments • data sheet • formal report

FINAL EXAMINATION

Grading System The performance of the student in the laboratory is evaluated in terms of the following:: 10% attendance, 30% quizzes, 30% departmentalized long examination, 5% pre-lab assignment, 5% post-lab assignment, 5% data sheet, and 15% formal report for the first grading period and 10% attendance, 20% quizzes, 30% departmentalized long examination, 10% practical examinations (analysis of unknowns), 5% pre-lab assignment, 5% post-lab assignment, 5% data sheet, and 15% formal report for the second grading period. Course References Basic readings: Laboratory Manual in Organic Chemistry. Organic Chemistry Group. 2009. UST Faculty of Pharmacy Extended Readings: th Landgrebe, J. A. Theory and Practice in the Organic Chemistry Laboratory with Microscale and Standard Scale Experiments. 5 ed. California: Pacific Grove, 2005 Mayo, D., Pike, R., Bucher, S., and Trumper, P. Microscale Techniques Organic Laboratory. New York: Wiley, 1991. Pasto, D., Johnson, C., and Miller, M. Experiments and Techniques in Organic Chemistry. New Jersey: Prentice-Hall, 1998. Wilcox, C. and Wilcox, M. Experimental Organic Chemistry-A Small Scale Approach Techniques. New Jersey: Prentice-Hall, 1995. Web-based: www.darmouth.edu/chemexp/ www.miracosta.edu/home/dlr/21exp.htm www.home.nas.net/dbc/cic_hamilton/org.html Instructional Media: transparencies power point presentations Prepared by: Organic Chemistry Group of the Department of Biochemistry Date: revised March 29, 2012

Approved by: Prof. Priscilla M. Torres, Ph.D. Date: 15 April 2012

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