Sample Organic Chemistry Outline 1246
Sample Organic Chemistry Outline 1246
Sample Organic Chemistry Outline 1246
Chemistry
Other Required Materials: Study Guide and Solutions Manual for McMurry's
OUTLINE
Problems: 1-13,16-18,24-28,40, 42
and Cycloalkanes Problems: 1, 3, 4, 6. 11-14, 17, 18, 21, 25, 27-31, 33, 34, 37
Reactivity Problems:1-12,13 (a.b,d), 14(a,b,d), 15, 18, 19 (a-c), 20, 22 (a-d), 26, 27, 32, 36 (a-c), 39,40
Synthesis Problems: 2-6, 9, 10, 13, 14 (a,b), 15, 16, 21, 22 (a-c), 23(a-c) 24 (a, b, d-f), 25- 31, 34, 35 (b-d), 44,
48
Problems: 1 ( a,b,d-f), 2, 10, 11, 15, 20 (c,d), 21 (a,f), 33 (a-c), 34 (a,c,d), 37, 38
Problems: 10,11,13,29-32
1, 3, 4; Table 4: all;
C. (p. 63 1)
spectrometry
Problems: 1, 2,49 59 6 (a,c), 7 (a,c), 8- 11, 13, 141,16, 17, 2 1, 23 (a-c,e , f, h), 25, 27-30, 37,41,52
Reactions Student: Much of the material in this short chapter will have been covered at this stage. You should use
Chapter 5 as a review for the final examination.
SAMPLE CHEMISTRY
Chapter 9 Stereochemistry
Laboratory Program:
Sample Chemistry
Other Required Materials: Study Guide and Solutions Manual for McMurrys
OUTLINE
Problems: 1, 3-5,8-14,16,19 (omit d), 21, 22 (ab), 24 (a,c,e, f), 25, 27 (b-d), 281, 49 (b)
Problems: 1-3, 4 (c.d), 6-8, 13 -15, 23, 27 (a, c-g), 31,32, 34, 36. 38 (a,c), 41-43, 52,57
Problems: 1, 2, 4-,6, 9-11, 14, 15, 19(a-d), 20 (a-d), 26, 27, 31, 32 (b,c), 38 (b), 40, 41,45
Substitution Reactions 30,31,35,37,39,40 (a-g), 41, 42, 53, 57, 63-65, 66 (a,b)
Reactions Problems: 1-3, 8-11, 15, 16, 18, 19, 21-26, 28, 30-32, 37-39
the Gabriel synthesis, and the Hofmann and Curtius rearrangements),7 (omit Hofmannelimination), 9
Problems:1-3, 5-7, 12, 13,23,24 (a, b, c), 25 (a, c, e, f), 28 (a, b, e, f, g), 36, 41, 42, 52
Electrophilic Aromatic Substitutions Problems: 3, 5,8-12, 14, 18, 19, 22,26 (a,b), 28, 29, 31-3 3,38-41,44 (c),
46,49 (b-d), 49 (a,b), 65 (a),66
Chapter 25 Arylamines and Phenol Sections: 1,2,3 (omit diazonium coupling rections, pp.984-985), 4-7, 8 (omit
Kolbe-Schmitt carboxylation reaction, ooxidation of phenols, Claisen rearrangement, pp. 993-997), 9
Problems: 1, 2, 4-7. 11, 13, 14,19,21 (a,c,e), 26, 27, 28 (a-e,h), 29 (a,b), 32, 39, 44,45
Chapter 27: Biomolecules: Amino Acids Sections: 1-3, 4 (reductive amination and Peptides and Proteins,
amidomalonate synthesis only), 5, 6, 8-10
Problems: 1, 4, 10, 11
SAMPLE CHEMISTRY
Review
Chapter 24 Carbohydrates
Chapter 28 Lipids
LABORATORY PROGRAM
Program
IR instruction
E4 - Day 2
19 - Day 2
E22 - Day 2
Check Out
SAMPLE CHEMISTRY COURSE OUTLINE
By doing problems, you can assess your progress. be stimulated to think ahead, and ultimately prepare for
examinations. In addition to doing problems from the Chem 231 problems set or problems within the text portion of
the chapters a significant number of the problems found at the end of each chapter should also be done. To do well
in this course it is essential to have mastered the ability to do organic chemistry problems. This goal can only be
reached by actively working problems - reading your notes or the textbook or memorization of lists of standard
chemical reactions will not be sufficient to do well in this course. Organic chemistry is much like a language and is a
course which cannot be "crammed". It is strongly recommended that you follow an ongoing program of study for
this course.
The topics and key phrases describing important concepts to be covered in this course are given below. These
topics are presented in approximately chronological order and follow fairly closely the order of chapters in the text.
For problems (not mentioned below) that are contained in the body of each chapter. the answers we found at the
back of the textbook. The "additional" problems that are given below am also pertinent and the answers for these
are found in the Solutions Manual and Study Guide. Together with the questions (and answers) given in the Chem
231 problems sets these exercises and problems largely define the scope of the course. In order to be sure that you
understand the course material it is strongly advised that you routinely do as many of these problems as is
possible.
Review of bonding: covalent and polar bonds, Lewis structures. bonding in methane. ethane. ethene ethyne methyl
cation radical and anion, bond angles, dipole moment acidity and basicity. Lewis acids and Lewis bases
constitutional isomers (structural isomers), nomenclature or organic compounds (including cycloalkanes). iso- and
neo- structures, common names, review of various functional groups, primary secondary, tertiary. carbons and
hydrogens: quaternary carbon and nitrogen, conformations of alkanes and of cyclohexane: staggered/ eclipsed
conformations; anti/gauche conformers steric strain, angle strain: chair conformations, axial and equatorial bonds
in cyclohexanes, ring-flipping
Chapter 3: All sections (except omit 3.16, 3.18): Additional Problems: 3.39 - 3.42. 45, 46, 55
cis-trans isomerism, E.Z system of nomenclature, reaction coordinate diagrams, electrophilic addition reactions:
addition of hydrogen halides, of water, of alcohol, of halogens, of diborane (hydroboration-oxidation), of hydrogen
(hydrogenation) relative stabilities of carbocations including allylic and benzylic systems (See Chapter 6: 6.4-6.10)
STEREOCHEMISTRY (Chapter 4)
conformational isomers, configurational isomers, stereogenic centres , R,S system of nomenclature isomers with
more than one stereogenic centre, meso-compounds, resolution of racemic mixtures, conformations of substituted
cyclohexanes stereochemistry of addition reactions: bromonium ion intermediate hydrogenations. hydroboration-
oxidation
Chapter 5: All sections (except omit 5.7)-. Additional Problems: 5.20. 22, 31.32.34
structure of alkynes addition of halogens, of water (tautomers, keto-enol isomerization), of hydrogen. acetylide ions
and their use in synthesis.
Chapter 8: All sections (except omit 8.7 and 8.8); Additional Problems: 8.18, 21
free radical chain reaction mechanism for chlorination, factors in product distribution,
relative stabilities of radicals including allylic and benzylic systems (See Chapter 6: 6.4-6-10)
Infrared Spectroscopy Chapter 12: Section 12.7 and 12,8 (OK NH, and C=O absorption bands. e.g. spectra in
Figures 12.18 to 12.23).
Infrared spectra and origin of absortion bands for alcohols, wines, and carbonyl compounds
Nmr spectroscopy, Chapter 14: Sections 14.1 to 14.6. Additional problems, 14.3, 14.4, 14.11. 14.13, 14.20. 14-21,
14-25, Origin of an NMR signal, chemical equivalent protons, characteristic chemical shifts. integration of NMR
signals, spin-spin splitting, i.e.. doublets. triplets quartets, etc.
Chapter 9; All sections (except omit 9.10, 9.12, 9.17. 9.20, 9.21): Additional Problems: 9.51. 9.54
SUBSTITUTION AND ELIMINATION REACTIONS (II) Leaving groups other than, halogen) (Chapter 10)
Chapter 10: All sections (except omit 10.5, 10.9, 10.10, 10.11, 10.12; Additional Problems: 10.30.32
Substitution and dehydration reactions of alcohols, substitutions of sulfonate esters of ethers reactions of epoxides,
organometallic compounds
Chapter 11: All sections (except omit 11.13, 11.14); Additional Problems: 11.27, 11.32, 11.33
catalytic hydrogenation. hydride reductions, oxidation of alcohols, aldehydes, alkenes (hydroxylation, ozonolysis)
(Spring 1998)
This course is the continuation of Chemistry 231 which is a required prerequisite course. The chapter references an
to "Organic Chemistry" by Paula Y. Bruice. Topics covered and reading assignments may be modified by individual
instructors.
As in Chem 231, you can assess your progress, be stimulated to think ahead, and ultimately prepare for
examinations by doing problems. In addition to doing problems from the Chem 232 problems set or problems within
the text portion of the chapter a significant number of the problems found at the end of each chapter should also be
done. To do well in this course it is essential to have mastered the ability to do organic chemistry problems. This
goal can only be reached by actively working problems - reading your notes or the textbook or memorization of list
of standard chemical reactions will riot be sufficient to do well in this course. Organic chemistry is much like a
language and is a course which cannot be "crammed". It is strongly recommended that you follow an ongoing
program of study for this course.
The topics and key phrases describing important concepts to be covered in this course are given below. The topics
we presented in approximately chronological order and follow will closely the order of chapters in the text.
For problems (not mentioned below) that are contained in the body of each chapter. The answers are found at the
back of the textbook. The "additional" problems that are given below are also pertinent and the answers for these
are found in the Solutions Manual and Study Guide. Together with the questions (and answers) given in the Chem
232 problems sets these exercises and problems largely define the scope of the course. In order to be sure that you
understand the course material it is strongly advised that you routinely do as many of these problems as is
possible.
Nucleophiles.
Nomenclature or aldthydes and ketones. General reactivity considerations, relative reactivities or aldehydes and
ketones. Addition of various nucleophiles to the carbonyl group A. Addition or Grignard reagents to product alcohols
and (with carbon dioxide) acids B. Addition of acetylide anions and of hydrogen cyanide C. Addition of hydride ion
(NaBH4 and LiAlHA) D. Addition of primary amines and derivaties of primary amines B. Addition of oxygen
nucleophiles (water and alcohols) –acetal/ketall formation
Chapter 18: All sections except omit oxidative cleavage in 1B.S. also omit 18.8 and 18.15 through 19.19) Additional
Problems. l8.29a,b,c.d,t4,h- 18.30a.b, 19,36.
Osazone formation
Cyclic structure of monosaccharides: hemiactial formation, formation of glycosides Fischer, Haworth and
conformational representations Formation of esters and ethers Examples of disaccharides and polysaccharides
(starch and cellulose)
CARBONYL COMPOUNDS I (Chapter IS) Reaction or Carboxylic Acids and their Derivatives with Oxygen and
Nitrogen Nucleophiles. Nucleophilic Acyl Substitution Reactions
Chapter IS: All sections except section 15.16 (after page 744) and section 15.17,
Nomenclature of carboxylic acids. acyl halides, acid anhydrides, esters amides nitriles
Mechanism for Nucleophilic Acyl Substitution reactions (acidic and basic conditions)
acid-catalyzed ester hydrolysis; hydroxide ion promoted ester hydrolysis; hydrolysis of Amides and of nitriles
Reaction of Grignard reagents and hydride ion with esters and acid chlorides
CARBONYL COMPOUNDS III (Chapter 17) Reactions at the a-Carbon of Carbonyl Compounds.
Chapter 17: All sections except 17.5 through 17.10. 17.20 and 17.21.
Acidity of hydrogen bonded to an a-carbon of aldehydes and keto-enol Lautomerization Reactivitv considerations:
Chapter 13: 13.1 to 13.20 (but omit 13.6. 13.9 and 13.19) Also omit 13.20 to 13-25.
Nomenclature of substituted benzenes and review of bonding in benzene Reactivity considerations, general
methanism for clectrophific aromatic substitution reiactions Halogenation of benzene. nitration of benzene. Friedel-
Crafts scylation, Friedel-Crafts alkylation. The effect of substituents on reactivity-, inductive effects and resonance
effects. The effect of substituents on orientation and rate of reaction. synthesis of poly-substituted aromatics
Reduction of nitro groups and synthesis of using diazonium ions (displacement reactions only) Effects of the
benzene ring on substituent groups Enhanced reactivity of the benzylic position: halogenation or side chain alkyl
groups; east of displacement at the benzylic position; oxidation of side chain alkyl groups The effect of substituents
on the pX, and pKb of aromatic acids, phenols and &mines
Classification, stereochemistry and nomenclature of amino acids, Acid-base properties of amino acids: isoelectric
point of amino acids Peptide structures (dipeptides and relevance to polypeptides and proteins) Synthesis of amino
acids
Laboratory
The laboratory consists of experiments that illustrate the properties of organic compounds and the techniques used
to investigate and produce organic materials. Although changes and substitutions are commonly made the
individual experiments will be similar to those given below
Chem 231
Chem 232
3. Recrystallization
2, Esters
3. Carbonyl Compounds, Aldehydes and ketones .(Tests for and reactions of Carbonyl Compounds)
4. Trimyristin from Nutmeg [three weeks) (Isolation and Characterization of an organic natural product).
SAMPLE CHEMISTRY
Course Outline
Course Description
Chemistry 260 covers organic chemistry for Chemical Engineers and other students of Applied Science. Also for
Forestry students in Business Management & Marketing and Industrial Processing Technology options.
A description of the properties and reactions of organic compounds with emphasis on compounds and reactions of
industrial importance.
Text
Organic Chemistry, Fourth Edition, by John McMurray, Brooks/Cole Publishing Company, Pacific Grove, CA, 1992
Study Guide and Solutions Manual for Organic Chemistry, Fourth Edition, by Susan McMurray, Brooks/Cole
Publishing Company, Pacific Grove, CA, 1992
Reference Books
Industrial organic chemistry, Klaus Weissermel, Hans-Jurgen Arpe; translated by Charles R. Lindley, 2nd ed,
Weinheim -, New York, 1993
Executive editor, Jacqueline I. Kroschwitz ; Editor, Mary Howe-Grant, John Wiley and Sons, New York, 1992
An Introduction to Industrial Organic Chemistry, (2nd Ed.), P. Wiseman, Applied Science Publishers, Ltd., London,
1979.
Polymer Science and Technology, Joel R. Fried, Prentice-Hall, Englewood Cliffs, New Jersey, 1995.
This course will include a description of the important functional groups with emphasis on the following aspects of
the subject: (a) reactions of industrial importance, (b) the relationship between common and IUPAC nomenclatures,
and (c) the relationship between structure and physical properties. The important reactions of functional groups and
the fundamentals of mechanism will be considered.
SYLLABUS
6. Alcohols, phenols, and ethers: properties, reactions, and uses; commercial production of
phenol, ethanol, and ethylene glycol.
7. Carbonyl compounds: aldehydes and ketones, properties, reactions and uses; commercial
preparations of acetone.
8. Carboxylic acids: acidity, esters, fats, oils, detergents, micelles, surfactants.
DMSO.
13. Biotechnology: DNA, RNA, tissue culture, cloning, recombinant DNA technology.