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DEPARTMENT OF PHYSICAL SCIENCES AND MATHEMATICS

College of Arts and Sciences


University of the Philippines, Manila

CHEMISTRY 31

Course Title: Elementary Organic Chemistry


Course Description: Study of structure and nomenclature of simple organic compounds, the
consequences of structure on the physical properties and on the reactions these
compounds commonly undergo, and the mechanism of these reactions.
Credit: 3 units lecture
General Objective: To enable the student to know and understand the fundamental concepts of
organic chemistry in preparation for advanced courses in the life sciences.

Course Outline

I. STRUCTURE OF CARBON At the end of the unit, the students should be able to:
A. HYBRIDIZED ORBITALS OF CARBON 1. Discuss the versatility of carbon, making it the
1. Electronic configuration of carbon principal element in organic compounds.
2. Hybridization (sp,sp2,sp3 hybrid orbitals) 2. Predict the type of hybridization of carbon atoms in a
3. Geometry of hybrid orbitals compound.
4. s and p character of hybrid atomic orbitals 3. Draw the molecular orbital picture of simple organic
B. THE COVALENT BOND compounds.
1. Characteristics of sigma and pi orbitals 4. Convert condensed formula of organic compounds
2. Formation of covalent bonds into the structural formula, and vice versa.
3. Properties of covalent bonds 5. Predict the geometry of organic compounds from the
3.1 Bond length experimentally observed bond angles of inorganic
3.2 Bond angle compounds.
3.3 Bond strength 6. Recognize how organic compounds are formed by
3.4 Bond polarity overlapping of atomic and hybrid orbitals.
3.5 Bond order 7. Predict and explain variations in the properties of
covalent bonds existing in different molecular
structures.

II. CLASSIFICATION AND NOMENCLATURE OF At the end of the unit, the students should be able to:
ORGANIC COMPOUNDS 1. Classify organic compounds according to composition
A. HYDROCARBONS and functional groups.
1. Unsaturated hydrocarbons 2. Write the structural formulas and give the
2. Saturated hydrocarbons corresponding IUPAC and/or common name of
3. Index of hydrogen deficiency organic compounds.
B. FUNCTIONAL GROUPS 3. Determine the index of hydrogen deficiency for each
1. Group I: Halides, Alcohols, Ethers, Amines, formula and write both the cyclic and acyclic
Thiols, Thioethers structure to fit each formula.
2. Group II: Aldehydes, Ketones, Imines, Acetals, 4. Identify the functional group of each class of organic
Oximes, Hydrazones compound.
3. Group III: Nitriles, Acid Halides, Carboxylic 5. Give examples of biological importance of each class
Acids, Esters, Anhydrides, Amides of organic compounds.
4. Index of Hydrogen Deficiency (Halogen, Oxygen,
and Nitrogen Compounds)
C. NOMENCLATURE OF ORGANIC COMPOUNDS
III. STRUCTURE OF ORGANIC COMPOUNDS At the end of the unit, the students should be able to:
A. ISOMERISM 1. Differentiate between structural isomers and
1. Structural isomers (chain, functional, positional) stereoisomers.
2. Stereoisomers 2. Differentiate between configurational isomers and
2.1 Conformational isomers conformational isomers.
2.2 Conformational analysis 3. Analyze the different types of conformations.
2.3 Geometric isomers 4. Identify the factors used to predict the stability of
2.4 E,Z nomenclature of geometric isomers conformations.
2.5 Optical isomers 5. Identify the different kinds of configurational isomers
2.6 R,S nomenclature of optical isomers and their properties.

FIRST DEPARTMENTAL EXAMINATION FIRST DEPARTMENTAL EXAMINATION

IV. STRUCTURAL EFFECTS ON PHYSICAL AND At the end of the unit, the students should be able to:
CHEMICAL PROPERTIES 1. Define and correlate the various structural effects
A. STRUCTURAL EFFECTS with the different properties of organic compounds.
1. Resonance (pi electron delocalization) 2. Describe the different intermolecular forces of
2. C-H hyperconjugation attraction.
3. Van der Waals interaction 3. Compare the boiling points and melting points of
4. Hydrogen bonding branched and linear hydrocarbons; open and cyclic
5. Steric effects hydrocarbons; and hydrocarbon derivatives.
6. Inductive effects 4. Differentiate between polar and nonpolar solvents;
B. BOILING POINT AND MELTING POINT protic and aprotic solvents; hydrophobic and
1. Intermolecular attractions: London forces, hydrophilic compounds.
dipole-dipole interactions; hydrogen bonding 5. Predict the solubility of a particular organic
2. Effect of carbon chain length compound in polar and nonpolar solvents; protic and
3. Effect of carbon branching aprotic solvents.
4. Effect of molecular symmetry (cis-trans for 6. Explain the acidity and basicity of a particular organic
geometric isomers; ortho-para for aromatic compound based on resonance and inductive effects.
compounds) 7. Compare the acidity of organic compounds when
5. Effect of polarity dissolved in two kinds of solvents.
6. Effect of functional groups that are capable of 8. Identify aromatic compounds.
H-bonding interactions (intermolecular and
intramolecular H-bonding)
C. SOLUBILITY
1. Polar and nonpolar solvents
2. Protic and aprotic polar solvents
3. Hydrophilic and hydrophobic compounds
4. Effect of carbon chain length
5. Effect of polar functional groups
D. ACIDITY AND BASICITY
1. pKa and pKb of parent carbon acids, nitrogen
acids, and oxygen acids
2. Strength of conjugate base
3. Structural effects on acidity and basicity
E. AROMATICITY
1. Structural properties of compounds that exhibit
aromaticity
2. Huckel rule
3. Stability of aromatic compounds
V. INTRODUCTION TO ORGANIC REACTIONS At the end of the unit, the students should be able to:
A. CHARACTERISTIC REACTION OF ORGANIC 1. Enumerate the general characteristic reactions of
COMPOUNDS organic compounds.
1. Acid-base reaction 2. Predict the type of reaction (substitution, elimination,
2. Reactions that make or break bonds redox, rearrangement)
2.1 Addition 3. Identify the type of bond breaking (homolytic or
2.2 Substitution heterolytic breaking)
2.3 Elimination 4. Evaluate the stability of the different kinds of
2.4 Rearrangement reaction intermediates.
3. Redox reaction 5. Differentiate concerted and multitstep reaction
B. TYPES OF BOND CLEAVAGE: HOMOLYTIC AND processes.
HETEROLYTIC BREAKING 6. Differentiate between electrophiles and nucleophiles.
C. TYPES OF REACTION INTERMEDIATES AND 7. Differentiate between nucleophilicity and basicity.
MECHANISM 8. Evaluate the strength of nucleophiles.
1. Concerted and multistep processes 9. Determine the oxidation number of carbon in organic
2. Stability of intermediates compounds.
D. MAJOR CLASSES OF REACTIVE PARTICLES
1. Electrophiles and nucleophiles
2. Strength of nucleophiles

SECOND DEPARTMENTAL EXAMINATION SECOND DEPARTMENTAL EXAMINATION

VI. REACTIONS INVOLVING ELECTROPHILIC


REAGENTS

A. FREE RADICAL SUBSTITUTION AT SATURATED At the end of the unit, the students should be able to:
CARBON 1. Show the mechanism of free radical substitution
1. Free radical mechanism of halogenations reaction.
2. Relative reactivity of halogens to free radical 2. Define the condition that will limit substitution to
substitution reaction monohalogenation.
3. Relative reactivity of alkanes to halogenation 3. Predict the number of monohalogenation products
reaction possible for a given alkane.
4. Evaluate the reactivity of halogenation reaction
(chlorination vs bromination)
5. Determine the percentage yield of monohalogenated
products.

B. ELECTROPHILIC ADDITION At the end of the unit, the students should be able to:
1. General reaction mechanism of electrophilic 1. Show the mechanism of electrophilic addition
addition reaction reaction.
2. Direction and stereochemistry of added 2. Predict the orientation and position of added
substituent substituent to alkenes.
3. Orientation and position of added substituent 3. Compare the stability of the reactive intermediates.
4. Relative rates of carbonium ion intermediates 4. Compare electrophilic addition reactions of alkenes
5. Addition reactions of alkenes and alkynes.
6. Addition reactions of alkynes 5. Show the mechanism of conjugate addition reaction.
7. Mechanism of conjugate addition reaction 6. Determine the major product of conjugate addition
8. 1,2 and 1,4-addition reactions of butadiene reaction.
C. ELECTROPHILIC AROMATIC SUBSTITUTION At the end of the unit, the students should be able to:
1. The benzene ring: geometry and pi electrons 1. Show the mechanism of electrophilic aromatic
2. Mechanism of electrophilic aromatic substitution substitution.
2.1 Generation of electrophiles 2. Identify ortho-para and meta directors.
2.2 Attack of electrophiles on the aromatic 3. Explain the effect of substituents on the reactivity of
ring aromatic compounds.
2.3 Resonance structure of benzeneonium ion 4. Predict the reactivity of monosubstituted and
2.4 Neutralization of benzeneonium and disubstituted benzene towards electrophilic aromatic
generation of catalysts substitution.
3. Effect of substituent groups on reactivity and 5. Predict the orientation of incoming substituent in
orientation mono- and disubstituted benzene.
4. Classification of substituents: ortho, para, meta 6. Explain why halogen atoms are ortho-para directors.
directors; activating, deactivating groups 7. Know the limitations of Friedel-Crafts alkylation and
5. Molecular basis of reactivity and orientation acylation reactions.
5.1 Electron release via resonance 8. Synthesize aromatic compounds.
5.2 Inductive effect
5.3 Effect of halogens: deactivating, ortho-
para directors
6. Reactivity of disubstituted benzene
7. Limitation of Friedel-Crafts alkylation/acylation
reaction
8. Oxidation of alkylbenzene and reduction of
acetophenone
9. Synthesis of organic compounds

VII. REACTIONS INVOLVING NUCLEOPHILIC


REAGENTS

A. NUCLEOPHILIC AROMATIC SUBSTITUTION At the end of the unit, the students should be able to:
1. Reactivity towards nucleophilic aromatic 1. Identify the conditions necessary for a compound to
substitution undergo nucleophilic aromatic substitution.
2. Introduction of nucleophiles to benzene ring 2. Show the mechanism for the formation of diazonium
through diazotization salt.
3. Mechanism of diazotization for primary and 3. Write some nucleophilic substitution reactions of
secondary amines diazonium salts.
4. Stability of aromatic diazonium ion
5. Organic synthesis of dye

THIRD DEPARTMENTAL EXAMINATION THIRD DEPARTMENTAL EXAMINATION


B. NUCLEOPHILIC SUBSTITUTION AT SATURATED At the end of the unit, the students should be able to:
CARBON 1. Compare the reactivity of alkyl halides towards SN1
1. Mechanism of SN1 and SN2 reactions and SN2 reactions.
2. Stereochemistry of SN1/SN2 2. Show the mechanism of SN1 and SN2 reactions.
3. Rate of SN1/SN2 reactions 3. Identify the conditions that favour SN1 and SN2.
4. Factors affecting rate of SN1/SN2 reactions 4. Differentiate stereochemistry of SN1 and SN2
4.1 Nature of substrate reactions.
4.2 Strength of nucleophiles 5. Predict when elimination can compete with
4.3 Nature of leaving group substitution.
4.4 Effect of solvent 6. Show the mechanism of substitution reaction of
5. Competing reactions: elimination, rearrangement alcohols (SN1 and SN2).
6. Substitution reactions of alcohols and ethers 7. Show the mechanism of substitution reaction of
7. Intramolecular substitution reactions ethers.
8. Show the mechanism of intramolecular substitution
reactions.

C. ELIMINATION At the end of the unit, the students should be able to:
1. Mechanism of E1/E2 reactions 1. Show E1 and E2 mechanisms.
2. Conditions favouring elimination reactions: 2. Identify the conditions favouring elimination
strong bases, higher temperature reactions.
3. Reactivity of substrates towards elimination 3. Compare the reactivity of alkyl halides and alcohols
reactions towards elimination reactions.
4. Stability of alkenes 4. Compare the mechanisms of dehydration of alcohols
5. Hoffmann elimination reaction and dehydration of alkyl halides.
5. Predict the major product based on the Zaitsev rule.
6. Know the conditions that favour Hofmann elimination
reactions.

D. NUCLEOPHILIC ADDITION TO UNSATURATED At the end of the unit, the students should be able to:
CARBON (CARBONYL AND RELATED GROUPS) 1. Illustrate the acid and base catalyzed addition
1. Mechanism of acid-catalysed and base-catalysed reaction mechanisms of aldehydes and ketones.
reaction 2. Recognize the factors affecting the reactivity of
2. Factors affecting reactivity of carbon groups carbonyl groups.
2.1 Resonance 3. Compare the reactivity of some carbon-containing
2.2 Inductive effect compounds.
2.3 Steric effect 4. Predict the mechanism of addition of HCN and
3. Simple addition reaction NaHSO3 to aldehydes and ketones.
3.1 Addition of HCN 5. Show the mechanism of the following reactions:
3.2 Addition of NaHSO3 haloform reaction, aldol condensation, acetal and
3.3 Haloform reaction hemiacetal formation, condensation reaction of
3.4 Addition of Grignard Reagent nitrogen compounds, and Grignard reaction.
3.5 Addition reaction of conjugated 6. Identify the nucleophiles that will favor conjugate
aldehydes/ketones addition and direct addition to conjugated aldehydes
3.6 Mechanism of aldol condensation and and ketones.
Cannizzaro reaction 7. Show the mechanism of Strecker synthesis of amino
4. Addition followed by elimination acids.
4.1 Condensation reaction with nitrogen
compounds
4.2 Acetal and hemiacetal formation
4.3 Strecker synthesis of amino acids
E. NUCLEOPHILIC SUBSTITUTION AT UNSATURATED At the end of the unit, the students should be able to:
CARBON 1. Recognize carboxylic acids and their derivatives.
1. Mechanism of nucleophilic substitution 2. Explain the reactivity of carboxylic acids and their
2. Reactivity of leaving groups in carboxylic acid derivatives.
derivatives 3. Compare the reactivity of base/nucleophiles to
2.1 Basicity of leaving groups compounds containing saturated and unsaturated
2.2 Resonance of substances carbon (e.g. acyl chlorides and alkyl chlorides,
2.3 Comparative reaction of bases or amides and amines).
nucleophiles to saturated and unsaturated
carbon
3. Reactions of carboxylic acid derivatives
3.1 Esterification and trans-esterification
3.2 Base hydrolysis of esters: saponification
3.3 Synthesis of anhydrides
3.4 Synthesis of aspirin and oil of wintergreen

VIII. REDOX REACTIONS At the end of the unit, the students should be able to:
A. COMMON OXIDIZING AND REDUCING AGENTS 1. Identify some oxidizing and reducing agents.
B. SOME USES OF REDOX REACTIONS 2. Cite some redox reactions in:
1. In qualitative analysis a. Qualitative analysis of some organic
1.1 Baeyer’s Test compounds
1.2 Tollen’s Test b. Organic synthesis
1.3 Fehling’s Test c. Structure determination of alkenes
1.4 Benedict’s Test
2 In organic synthesis
2.1 Oxidation with KMnO4, K2Cr2O7
2.2 Reduction
2.2.1 Catalytic Hydrogenation
2.2.2 Clemmensen Reduction
2.2.3 Reduction with LiAlH4/NaBH4
2.2.4 Reduction with Metal (Sn)
3. In structure determination: ozonolysis
3.1 Reductive ozonolysis
3.2 Oxidative ozonolysis

FOURTH DEPARTMENTAL EXAMINATION FOURTH DEPARTMENTAL EXAMINATION


Course Policies:

1. Any form of cheating during examinations shall be penalized according to the fullest extent of university rules and
regulations. The case against offenders shall be filed and referred to the highest authorities regarding scholastic
integrity and their future in the university. Furthermore, a grade of 5.0 is automatically given to the offenders and
they shall be blacklisted as cheaters in their succeeding semesters taking any chemistry subject in the division.
2. No makeup examination shall be given for whatever reason.
3. In case an examination is missed due to a valid reason, the final examination shall make up for the missed
examination. No more than two missed examinations shall be allowed.
4. A student is exempted from taking the final examination if the following conditions are met:
a. He/she has a class standing equivalent to a grade of 2.75 or better.
b. He/she has no grade lower than 40% in any of the long examinations.
5. At the end of the semester, grades shall be computed as follows:
a. If the student takes the final examination, his or her grade shall be computed according to the following
percentage distribution:
Class Standing: 2/3
Final Examination: 1/3
b. If a student is exempted from taking the final examination and did not take it, then his or her grade shall be
the equivalent grade of his or her class standing.
c. If a student is not exempted but failed to take the final examination for whatever reason, he or she gets a
grade of 5.0.

Course Requirements:

 Four (4) Departmental Examinations 80%


 Quizzes 20%
 Pre-Final Grade 100%

Pre-Final Grade 2/3


Final Examination 1/3
Final Grade 1

Grading Scale:

90-100 1.00 65-69 2.25


85-89 1.25 60-64 2.50
80-84 1.50 55-59 2.75
75-79 1.75 50-54 3.00
70-74 2.00 40-49 4.00
0-39 5.00

Christopher Jay T. Robidillo, MS


Summer, AY 2011-2012

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