Identification
Subject
(code, title,
credits)
Department
Program
(undergraduate,
graduate)
Term
Instructor
E-mail:
Phone:
Organic CHEMISTRY (3 credits)
Chemistry/Chemical Engineering
Undergraduate
Autumn 2015
Dr. Jestin Mandumpal
jmandumpal@khazar.org or dejesman@gmail.com
+994 514142095
Prerequisites
This course is a prerequisite for Chemical Engineering courses studied further
Language
Compulsory/Elective
Required textbooks
and course materials
English
compulsory
Core textbooks
1. Organic Chemistry A Brief Course, Robert C. Atkins & Francis A.
Carey
2. Marie Anne Fox & James Whitsel Organic Chemistry
This course is based on traditional face-to-face classes
Introduction to Organic Chemistry: Chemical Bonding/ Alkanes and
Cycloalkanes/ Introduction to Organic Chemical Reactions/ Alkenes,
Alkdienes, and Alkynes: 1. Structure and Preparation & 2. Reactions/ Arenes
and Aromaticity/ Nucleophilic substitution reactions/Alcohols, Ethers and
Phenols/ Carboxylic acids.
Course website
Course outline
Course objectives
Learning outcomes
Teaching methods
General Objective of the Course
To meet curriculum requirements of the School of Engineering and Applied
Sciences (SEAS).
Specific Objectives of the Course
-To provide the student a strong foundations in Organic Chemistry.
-To encourage students participation and interaction in a scientific
environment
-To build background for the students further studying Chemical Engineering
courses
By the end of the course the students should be able
-To recognize the important Organic functional groups.
-To know reactions and preparatory methods of important Organic
compounds
To know certain reaction mechanisms.
To procure intuitive knowledge of how chemical reactions happen
Lecture
Group discussion
Experimental exercise
Case analysis
Simulation
Course paper
Others
x
x
x
Evaluation
Policy
Methods
Date/deadlines
Percentage (%)
November, 2014
30
Midterm Exam
20
Assignment and
quizzes
10
Presentation/Group
Discussion
May, 2015
40
Final Exam
100
Total
Attendance
The students are required to attend all classes as a part of their studies and
those having legitimate reasons for absence (illness, family bereavement, etc.)
are required to inform the instructor.
Tardiness / other disruptions.
If a student is late to the class for more than 10 (ten) minutes, (s)he is not
allowed to enter and disturb the class. However, this student is able to enter
the second double hours without delaying.
Exams
In order to be excused from the exam, the student must contact the dean and
the instructor before the exam. Excuse will not be granted for social activities
such as trips, cruises and sporting events (unless you are participating). The
exams will all be cumulative. Most of the questions on each exam will be
taken from the chapters covered since the last exam.
But some will come from the earlier chapters. In general the coverage will
reflect the amount of the time spend in class on the different chapters.
Withdrawal (pass / fail)
This course strictly follows grading policy of the School of Engineering and
Applied Sciences. Thus, a student is normally expected to achieve a mark of
at least 60% to pass. In this case of failure, he/she will be referred or required
to repeat the course the following term or year.
Cheating / plagiarism
Cheating or other plagiarism during midterm and final examinations will lead
to paper cancellation. In case, the student will automatically get 0 (zero),
without any considerations.
Professional behaviour guidelines
The student shall behave in the way to create favorable academic and
professional environment during the class hours. Unauthorized discussions
and unethical behavior are strictly prohibited.
For successful completion of the course, the students shall take an active part
during the class time, raising questions and involving others to discussions.
Learning and Teaching Methods
This course considers active learning process rather than passive one.
Week
1
Sept
15-21
2015
Tentative Schedule
Topics
Topic
1
i.
ii.
iii.
iv.
v.
vi.
vii.
viii.
ix.
x.
xi.
xii.
2
Sept
22- 28
2015
3
Sept 29Oct 4
2015
2
Introduction to Organic Chemistry
(1-20)
Atoms and electrons (2)
Ionic Bonding(4)
Covalent Bonding(5)
Polar Covalent Bonds(8)
Formal Charge(9)
Multiple
bonding
in
Lewis
structures(10)
Empirical and Molecular formulae(11)
Isomers and Isomerism(12)
Resonance(13)
The shapes
of some simple
molecules(16)
The Molecular Orbital view of
Bonding (19)
Review of the topic
Alkanes and Cycloalkanes (23−50)
Methane (24)
Orbital Hybridization and bonding in
methane (24)
iii.
Ethane and Propane (25)
iv.
Conformations of Ethane and Propane
(27)
v.
Isomeric Alkanes. The butanes (29)
vi.
Higher alkanes (30)
vii.
Systematic IUPAC Nomenclature of
Unbranched alkanes (33)
viii.
Applying IUPAC rules. The names of
the C6H14 isomers (34)
ix.
Alkyl groups (37)
x.
IUPAC names of highly branched
Alkanes (38)
xi.
Cyclohexane Nomenclature (39)
xii.
Conformations of Cyclopropane,
Cyclobutane, and Cyclopentane (40)
xiii. Conformations of Cyclohexane (41)
xiv. Conformational Inversion (Ringflipping) in Cyclohexane (44)
xv.
Disubstituted Cycloalkanes and sterero
isomerism (45)
xvi. Polycyclic alkanes (47)
xvii. Physical properties of alkanes (48)
xviii. Chemical properties of alkanes(49)
xix. Review of the topic
Textbook/Assignments
[1]
i.
ii.
2
[1]
[1]
4
3
Oct
5- 11
2015
5
Oct
12 –18
2015
3
Introduction to Organic Chemical Reactions
(55-83)
i.
Families of Organic Compounds
Hydro Carbons (56)
ii.
Functional groups in Hydrocarbons
(57)
iii.
Functionally substituted derivatives of
alkanes (58)
iv.
Nomenclature of alcohols and alkyl
halides(59)
v.
Classes of alcohols and alkyl
halides(62)
vi.
Bonding and Physical properties of
alcohols and alkyl halides (63)
vii.
Acid−Base properties of Organic
molecules (65)
viii. Alcohols as Brǿnsted Bases (68)
iii.
iv.
v.
vi.
vii.
viii.
ix.
x.
6
4
i.
Oct
19-25
2015
Preparation of alkyl halides (68)
Alkyl halides from alcohols and
hydrogen halides (69)
Mechanism of the reaction of alcohols
with Hydrogen Halides (70)
Structure and stability of Carbocations
(71)
Electrophiles and Nucleophiles(74)
Chlorination of methanes/mechanism
(75)
Free radicals (76)
Review of the topic
Alkenes, Alkadienes and Alkynes
Alkenes (80-95)
Nomenclature/Structure and Bonding
in ethylene, propene & higher
alkenes/Stereo
isomerism/Classification/Preparation of
alkenes/Elimination
Reactions/Dehydration of alcohols
(603)
[1]
[1]
[1]
7
Oct 26 –
Nov 1
2015
4
8
Nov
2-8
2015
1-4
9
Nov
16-22
2015
5
10
Nov
23-29
2015
6
11
Nov 30 –
Dec6
2015
6
Alkenes, Alkadienes and Alkynes (95−130)
i.
Alkadienes (105−107)
Classes of Dienes/Diene
Nomenclature/Bonding in conjugated
dienes/preparation of alakdienes
ii.
Alkynes (107)
Alkyne Nomenclature/Structure and
Bonding in Alkynes/Preparation of
Alkynes by Elimination reactions
iii.
Addition reactions of alkenes (118)
Hydrogenation/Electrophilic addition
of Hydrogen Halides to
Alkenes/Markovnikov’s
rule/Acid−catalysed hydration of
alkenes/Hydroboration
Oxidation/Addition of Halogens to
alkenes/Free−Radical Addition of
Hydrogen Bromide to alkenes (129)
Polymerisation of alkenes (130)
Review topics:: Introduction to Organic
Chemistry/Alkanes and Cycloalkanes/Introduction
to
Organic
Chemical
Reactions/Alkenes,
Alkadienes and Alkynes (up to page 130)
Midterm exam :: Nov 9-15 2015 topics 1 − 4
Alkenes, Alkadienes & Alkynes (131−150)
iv.
Cleavage of alkenes (131)
v.
Preparation of alkynes by alkylation
Reactions (138)
vi.
Addition reactions of alkynes (139)
vii.
Cleavage of alkynes (136)
viii. Acidity of Alkynes (136)
ix.
Preparation of Alkynes by Alkylation
Reactions (139)
x.
Addition reactions of Alkynes (139)
xi.
Cleavage of Alkynes (142)
xii.
Electrophilic Addition reactions of
Dienes (143)
xiii. The Diels Alder Reaction (145)
Review of the topic
Arenes and Aromaticity (155−187)
i.
Aromatic compounds (156)
ii.
Structure and Bonding of Benzene
(158)
iii.
An orbital Hybrodization model of
Bonding in Benzene(158)
iv.
Polycyclic Aromatic
Hydrocarbons(159)
v.
Nomenclature
of
Substituted
Derivatives of Benzene (160)
vi.
Reactions of Arenes: Electrophilic
Aromatic Substitution (163)
[1]
[1]
[1]
[1]
[1]
vii.
12
Dec
7 – 13
2015
6
13
7
Dec
14-20
2015
14
Dec
21-27
2015
Mechanism of Electrophilic Aromatic
Substitution (164)
viii. Intermediates
in
Electrophilic
Aromatic Substitution Reactions (165)
Nitration/Sulfonation/Halogenation/Fri
edel-Crafts
Alkylation
&
Acylation(165−168)
i.
Rate and Orientation in Electrophilic
Aromatic Substitution Reactions (169)
Rate effects of substituents/Orientation
effects of substituents (171)
ii.
Mechanistic explanation of rate and
orientation effects (172−176)
iii.
Synthesis of Di-substituted aromatic
compounds
iv.
Aromatic side−chain reactions
v.
A general view of Aromaticity. Hückel
rule
vi.
Heterocyclic Aromatic Compounds
(182)
vii. Review of the topic
Nucleophilic Substitution reactions (220−240)
i.
A review of Reaction mechanism
ii.
Nucleophilic Substitution
Reactions(221)
iii.
Relative Reactivity of Halide Leaving
groups(225)
iv.
Mechanisms of Nucleophilic
Substitution Reactions. A preview
(226)
v.
Bimolecular Nucleophilic Substitution.
The SN2 mechanism(226)
vi.
Stereochemistry of SN2 reactions(228)
vii.
Steric effects in SN2 reactions (229)
viii. The Unimolecular (SN1) mechanism of
Nucleophilic Substitution
ix.
Carbocation stability and the Rate of
substitution by SN1 mechanism
x.
Stereochemistry of SN1 Reactions
(234)
xi.
Substitution and Elimination as
Competing Reactions(236)
Primary alkyl halides/secondary alkyl
halides/tertiary alkyl halides
xii.
Review of the topic
8
i.
ii.
iii.
iv.
Alcohols, Ethers, and Phenols
(272−303)
Alcohols (273)
Natural source of Alcohols (275)
Reactions that lead to Alcohols (276)
Preparation of Alcohols by Reduction
of Aldehydes and ketones (277)
[1]
[1]
[1]
v.
vi.
vii.
viii.
ix.
x.
xi.
xii.
xiii.
xiv.
xv.
xvi.
15
Dec 28
(2015)Jan3
2016
9
Reactions of alcohols (279)
Alcohols as Bronsted Acids (281)
Conversion of alcohols to ethers (282)
Oxidation of Alcohols(282)
Introduction to ethers (286)
Ether nomenclature (286)
Ethers in nature (287)
Preparation of Ethers (288)
Preparation of epoxides (290)
Reactions of Epoxides(291)
Thiols (292)
Introduction to phenols: Nomenclature
(293)
xvii. Review of the topic
Aldehydes and Ketones (308−341)
i.
Nomenclature (309)
ii.
Structure and Bonding of the Carbonyl
group (311)
iii.
Physical Properties (313)
iv.
Sources of Aldehydes and Ketones
(313)
v.
Preparation of Aldehydes and Ketones
(314)
vi.
Reactions of Aldehydes and
Ketones(317)
vii.
Hydration of Aldehydes and Ketones:
A review and a preview (317)
viii. Hydration of Aldehydes and
Ketones(318)
ix.
Acetal formation (320)
x.
Cynohydrin Formation (322)
xi.
Reactions with Derivatives of
Ammonia (322)
xii.
Reactions that introduce new
Carbon−Carbon bonds (325)
xiii. Grignard Reagents (327 − 330)
xiv. The alpha Carbon and its Hydrogens
(332)
xv.
Enols and Enolates (333)
xvi. The Aldol condensation (335)
xvii. Oxidation of Aldehydes (338)
xviii. Review of the topic
Final exam Feb 2016 :: topics 5-9
This syllabus is a guide for the course and any modifications to it will be announced in advance.