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DEPARTMENT OF PHYSICAL SCIENCES AND MATHEMATICS

College of Arts and Sciences


University of the Philippines, Manila
CHEMISTRY 31
Course Title:
Course Description:

Credit:
General Objective:

Elementary Organic Chemistry


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.
3 units lecture
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
A. HYBRIDIZED ORBITALS OF CARBON
1. Electronic configuration of carbon
2. Hybridization (sp,sp2,sp3 hybrid orbitals)
3. Geometry of hybrid orbitals
4. s and p character of hybrid atomic orbitals
B. THE COVALENT BOND
1. Characteristics of sigma and pi orbitals
2. Formation of covalent bonds
3. Properties of covalent bonds
3.1 Bond length
3.2 Bond angle
3.3 Bond strength
3.4 Bond polarity
3.5 Bond order

II.

CLASSIFICATION AND NOMENCLATURE


OF ORGANIC COMPOUNDS
A. HYDROCARBONS
1. Unsaturated hydrocarbons
2. Saturated hydrocarbons
3. Index of hydrogen deficiency
B. FUNCTIONAL GROUPS
1.
Group I: Halides, Alcohols, Ethers,
Amines, Thiols, Thioethers
2.
Group II: Aldehydes, Ketones, Imines,
Acetals, Oximes, Hydrazones
3.
Group III: Nitriles, Acid Halides,
Carboxylic Acids, Esters, Anhydrides,
Amides
4.
Index
of
Hydrogen
Deficiency
(Halogen,
Oxygen,
and
Nitrogen
Compounds)
C. NOMENCLATURE OF ORGANIC COMPOUNDS

At the end of the unit, the students should be able


to:
1. Discuss the versatility of carbon, making it the
principal element in organic compounds.
2. Predict the type of hybridization of carbon
atoms in a compound.
3. Draw the molecular orbital picture of simple
organic compounds.
4. Convert condensed formula of organic
compounds into the structural formula, and
vice versa.
5. Predict the geometry of organic compounds
from the experimentally observed bond angles
of inorganic compounds.
6. Recognize how organic compounds are formed
by overlapping of atomic and hybrid orbitals.
7. Predict and explain variations in the properties
of covalent bonds existing in different
molecular structures.
At the end of the unit, the students should be able
to:
1. Classify organic compounds according to
composition and functional groups.
2. Write the structural formulas and give the
corresponding IUPAC and/or common name of
organic compounds.
3. Determine the index of hydrogen deficiency
for each formula and write both the cyclic and
acyclic structure to fit each formula.
4. Identify the functional group of each class of
organic compound.
5. Give examples of biological importance of
each class of organic compounds.

3.

III.

STRUCTURE OF ORGANIC COMPOUNDS


A. ISOMERISM
1. Structural isomers (chain, functional,
positional)
2. Stereoisomers
2.1 Conformational isomers
2.2 Conformational analysis
2.3 Geometric isomers
2.4 E,Z nomenclature of geometric
isomers
2.5 Optical isomers
2.6 R,S nomenclature of optical isomers
FIRST DEPARTMENTAL EXAMINATION

IV.

STRUCTURAL EFFECTS ON PHYSICAL


AND CHEMICAL PROPERTIES
A. STRUCTURAL EFFECTS
1. Resonance (pi electron delocalization)
2. C-H hyperconjugation
3. Van der Waals interaction
4. Hydrogen bonding
5. Steric effects
6. Inductive effects
B. BOILING POINT AND MELTING POINT
1. Intermolecular attractions: London forces,
dipole-dipole
interactions;
hydrogen
bonding
2. Effect of carbon chain length
3. Effect of carbon branching
4.
Effect of molecular symmetry (cistrans for geometric isomers; ortho-para
for aromatic compounds)
5. Effect of polarity
6.
Effect of functional groups that are
capable
of
H-bonding
interactions
(intermolecular and intramolecular Hbonding)
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

Stability of aromatic compounds

At the end of the unit, the students should be able


to:
1. Differentiate between structural isomers and
stereoisomers.
2. Differentiate between configurational isomers
and conformational isomers.
3. Analyze the different types of conformations.
4. Identify the factors used to predict the stability
of conformations.
5. Identify the different kinds of configurational
isomers and their properties.
FIRST DEPARTMENTAL EXAMINATION
At the end of the unit, the students should be able
to:
1. Define and correlate the various structural
effects with the different properties of organic
compounds.
2. Describe the different intermolecular forces of
attraction.
3. Compare the boiling points and melting points
of branched and linear hydrocarbons; open
and cyclic hydrocarbons; and hydrocarbon
derivatives.
4. Differentiate between polar and nonpolar
solvents;
protic
and
aprotic
solvents;
hydrophobic and hydrophilic compounds.
5. Predict the solubility of a particular organic
compound in polar and nonpolar solvents;
protic and aprotic solvents.
6. Explain the acidity and basicity of a particular
organic compound based on resonance and
inductive effects.
7. Compare the acidity of organic compounds
when dissolved in two kinds of solvents.
8. Identify aromatic compounds.

V. INTRODUCTION TO ORGANIC REACTIONS


A. CHARACTERISTIC REACTION OF ORGANIC
COMPOUNDS
1.
Acid-base reaction
2.
Reactions that make or break bonds
2.1 Addition
2.2 Substitution
2.3 Elimination
2.4 Rearrangement
3. Redox reaction
B. TYPES OF BOND CLEAVAGE: HOMOLYTIC AND
HETEROLYTIC BREAKING
C. TYPES OF REACTION INTERMEDIATES AND
MECHANISM
1.
Concerted and multistep processes
2.
Stability of intermediates
D. MAJOR CLASSES OF REACTIVE PARTICLES
1.
Electrophiles and nucleophiles
2. Strength of nucleophiles

At the end of the unit, the students should be able


to:
1. Enumerate the general characteristic reactions
of organic compounds.
2. Predict the type of reaction (substitution,
elimination, redox, rearrangement)
3. Identify the type of bond breaking (homolytic
or heterolytic breaking)
4. Evaluate the stability of the different kinds of
reaction intermediates.
5. Differentiate concerted and multitstep reaction
processes.
6. Differentiate
between
electrophiles
and
nucleophiles.
7. Differentiate between nucleophilicity and
basicity.
8. Evaluate the strength of nucleophiles.
9. Determine the oxidation number of carbon in
organic compounds.

SECOND DEPARTMENTAL EXAMINATION


VI.

REACTIONS
REAGENTS

INVOLVING

ELECTROPHILIC

A. FREE RADICAL SUBSTITUTION AT SATURATED


CARBON
1. Free radical mechanism of halogenations
2.
Relative reactivity of halogens to
free radical substitution reaction
3.
Relative reactivity of alkanes to
halogenation reaction

B. ELECTROPHILIC ADDITION
1.
General reaction mechanism of
electrophilic addition reaction
2.
Direction and stereochemistry of
added substituent
3.
Orientation and position of added
substituent
4.
Relative rates of carbonium ion
intermediates
5.
Addition reactions of alkenes
6.
Addition reactions of alkynes
7.
Mechanism of conjugate addition
reaction
8.
1,2 and 1,4-addition reactions of
butadiene

SECOND DEPARTMENTAL EXAMINATION

At the end of the unit, the students should be able


to:
1. Show the mechanism of free radical
substitution reaction.
2. Define the condition that will limit substitution
to monohalogenation.
3. Predict the number of monohalogenation
products possible for a given alkane.
4. Evaluate the reactivity of halogenation
reaction (chlorination vs bromination)
5. Determine
the
percentage
yield
of
monohalogenated products.

At the end of the unit, the students should be able


to:
1. Show the mechanism of electrophilic addition
reaction.
2. Predict the orientation and position of added
substituent to alkenes.
3. Compare the stability of the reactive
intermediates.
4. Compare electrophilic addition reactions of
alkenes and alkynes.
5. Show the mechanism of conjugate addition
reaction.

6. Determine the major product of conjugate


addition reaction.

C.

ELECTROPHILIC AROMATIC SUBSTITUTION


1.
The benzene ring: geometry and pi
electrons
2.
Mechanism of electrophilic aromatic
substitution
2.1
Generation of electrophiles
2.2
Attack of electrophiles on the
aromatic ring
2.3
Resonance
structure
of
benzeneonium ion
2.4
Neutralization of benzeneonium and
generation of catalysts
3. Effect of substituent groups on reactivity
and orientation
4. Classification of substituents: ortho, para,
meta directors; activating, deactivating
groups
5. Molecular
basis
of
reactivity
and
orientation
5.1
Electron release via resonance
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
REAGENTS

INVOLVING

NUCLEOPHILIC

A. NUCLEOPHILIC AROMATIC SUBSTITUTION


1.
Reactivity
towards
nucleophilic
aromatic substitution
2.
Introduction of nucleophiles to
benzene ring through diazotization
3.
Mechanism of diazotization for
primary and secondary amines
4.
Stability of aromatic diazonium ion
5.
Organic synthesis of dye
THIRD DEPARTMENTAL EXAMINATION

At the end of the unit, the students should be able


to:
1. Show the mechanism of electrophilic aromatic
substitution.
2. Identify ortho-para and meta directors.
3. Explain the effect of substituents on the
reactivity of aromatic compounds.
4. Predict the reactivity of monosubstituted and
disubstituted benzene towards electrophilic
aromatic substitution.
5. Predict the orientation of incoming substituent
in mono- and disubstituted benzene.
6. Explain why halogen atoms are ortho-para
directors.
7. Know the limitations of Friedel-Crafts alkylation
and acylation reactions.
8. Synthesize aromatic compounds.

At the end of the unit, the students should be able


to:
1. Identify the conditions necessary for a
compound to undergo nucleophilic aromatic
substitution.
2. Show the mechanism for the formation of
diazonium salt.
3. Write some nucleophilic substitution reactions
of diazonium salts.

THIRD DEPARTMENTAL EXAMINATION

4.2
4.3
B. NUCLEOPHILIC SUBSTITUTION AT SATURATED
CARBON
1.
Mechanism
of
SN1
and
SN2
reactions
2.
Stereochemistry of SN1/SN2
3.
Rate of SN1/SN2 reactions
4.
Factors affecting rate of SN1/SN2
reactions
4.1
Nature of substrate
4.2
Strength of nucleophiles
4.3
Nature of leaving group
4.4
Effect of solvent
5.
Competing reactions: elimination,
rearrangement
6. Substitution reactions of alcohols and
ethers
7. Intramolecular substitution reactions

C. ELIMINATION
1.
Mechanism of E1/E2 reactions
2.
Conditions
favouring
elimination
reactions:
strong
bases,
higher
temperature
3.
Reactivity of substrates towards
elimination reactions
4.
Stability of alkenes
5.
Hoffmann elimination reaction

D. NUCLEOPHILIC ADDITION TO UNSATURATED


CARBON (CARBONYL AND RELATED GROUPS)
1.
Mechanism of acid-catalysed and
base-catalysed reaction
2.
Factors affecting reactivity of carbon
groups
2.1
Resonance
2.2
Inductive effect
2.3
Steric effect
3.
Simple addition reaction
3.1
Addition of HCN
3.2
Addition of NaHSO3
3.3
Haloform reaction
3.4
Addition of Grignard Reagent
3.5
Addition reaction of conjugated
aldehydes/ketones
3.6
Mechanism of aldol condensation
and Cannizzaro reaction
4. Addition followed by elimination
4.1
Condensation reaction with nitrogen
compounds

Acetal and hemiacetal formation


Strecker synthesis of amino acids

At the end of the unit, the students should be able


to:
1. Compare the reactivity of alkyl halides towards
SN1 and SN2 reactions.
2. Show the mechanism of SN1 and SN2
reactions.
3. Identify the conditions that favour SN1 and
SN2.
4. Differentiate stereochemistry of SN1 and SN2
reactions.
5. Predict when elimination can compete with
substitution.
6. Show the mechanism of substitution reaction
of alcohols (SN1 and SN2).
7. Show the mechanism of substitution reaction
of ethers.
8. Show the mechanism of intramolecular
substitution reactions.
At the end of the unit, the students should be able
to:
1. Show E1 and E2 mechanisms.
2. Identify the conditions favouring elimination
reactions.
3. Compare the reactivity of alkyl halides and
alcohols towards elimination reactions.
4. Compare the mechanisms of dehydration of
alcohols and dehydration of alkyl halides.
5. Predict the major product based on the Zaitsev
rule.
6. Know the conditions that favour Hofmann
elimination reactions.
At the end of the unit, the students should be able
to:
1. Illustrate the acid and base catalyzed addition
reaction mechanisms of aldehydes and
ketones.
2. Recognize the factors affecting the reactivity
of carbonyl groups.
3. Compare the reactivity of some carboncontaining compounds.
4. Predict the mechanism of addition of HCN and
NaHSO3 to aldehydes and ketones.
5. Show the mechanism of the following
reactions:
haloform
reaction,
aldol
condensation,
acetal
and
hemiacetal
formation, condensation reaction of nitrogen
compounds, and Grignard reaction.
6. Identify the nucleophiles that will favor
conjugate addition and direct addition to
conjugated aldehydes and ketones.

7. Show the mechanism of Strecker synthesis of


amino acids.

E. NUCLEOPHILIC
SUBSTITUTION
AT
UNSATURATED CARBON
1.
Mechanism
of
nucleophilic
substitution
2.
Reactivity of leaving groups in
carboxylic acid derivatives
2.1
Basicity of leaving groups
2.2
Resonance of substances
2.3
Comparative reaction of bases or
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
A. COMMON
OXIDIZING
AND
REDUCING
AGENTS
B. SOME USES OF REDOX REACTIONS
1. In qualitative analysis
1.1
Baeyers Test
1.2
Tollens Test
1.3
Fehlings Test
1.4
Benedicts 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

At the end of the unit, the students should be able


to:
1. Recognize
carboxylic
acids
and
their
derivatives.
2. Explain the reactivity of carboxylic acids and
their derivatives.
3. Compare the reactivity of base/nucleophiles to
compounds
containing
saturated
and
unsaturated carbon (e.g. acyl chlorides and
alkyl chlorides, amides and amines).

At the end of the unit, the students should be able


to:
1. Identify some oxidizing and reducing agents.
2. Cite some redox reactions in:
a. Qualitative analysis of some organic
compounds
b. Organic synthesis
c. Structure determination of alkenes

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
Quizzes
Pre-Final Grade
Pre-Final Grade
Final Examination
Final Grade

2/3
1/3
1

Grading Scale:
90-100
85-89
80-84
75-79
70-74

1.00
1.25
1.50
1.75
2.00

80%
20%
100%

65-69
60-64
55-59
50-54
40-49
0-39

Christopher Jay T. Robidillo, MS


Summer, AY 2011-2012

prepared_by_threelegendz_summer_11_12

2.25
2.50
2.75
3.00
4.00
5.00