9/18/2014 Course Outline moorpark - CHEM M07B http://www.curricunet.com/moorpark/reports/course_outline_html.cfm?courses_id=3349 1/15 I. CATALOG INFORMATION A. Discipline: CHEMISTRY B. Subject Code and Number: CHEM M07B C. D. Credit Course units: Units: 5 Lecture Hours per week: 3 Lab Hours per week : 6 Variable Units : No E. Student Learning Hours: Lecture Hours: Classroom hours: 52.5 - 52.5 Laboratory/Activity Hours: Laboratory/Activity Hours 105 - 105 Total Combined Hours in a 17.5 week term: 157.5 - 157.5 F. Non-Credit Course hours per week G. May be taken a total of: X 1 2 3 4 time(s) for credit H. Is the course co-designated (same as) another course: No X Yes If YES, designate course Subject Code & Number: I. Course Description: Continues the study of functional groups such as carboxylic acids and their derivatives, other carbonyl-containing compounds, amines and aromatics. Emphasizes reaction mechanisms, synthesis, and structure determination using nuclear magnetic resonance and infrared spectroscopy. Introduces aspects of biochemistry including the study of proteins, carbohydrates, and nucleic acids. Involves, through laboratory work, multi-step synthetic routes, chromatography, and applications of basic techniques. J. Entrance Skills *Prerequisite: No Yes X Course(s) CHEM M07A, equivalent college course with a C or higher or *Corequisite: No X Yes Course(s) Limitation on Enrollment: No X Yes Recommended Preparation: No X Yes Course(s) Course Title: Organic Chemistry II
Laboratory/Activity Hours 105 - 105Total Combined Hours in a 17.5 week term: 157.5 - 157.5
F. Non-Credit Course hours per week
G. May be taken a total of: X 1 2 3 4 time(s) for credit
H. Is the course co-designated (same as) another course: No X Yes If YES, designate course Subject Code & Number:
I. Course Description:
Continues the study of functional groups such as carboxylic acids and theirderivatives, other carbonyl-containing compounds, amines and aromatics.Emphasizes reaction mechanisms, synthesis, and structure determination usingnuclear magnetic resonance and infrared spectroscopy. Introduces aspects ofbiochemistry including the study of proteins, carbohydrates, and nucleic acids.Involves, through laboratory work, multi-step synthetic routes, chromatography,and applications of basic techniques.
J. Entrance Skills
*Prerequisite: No Yes X Course(s) CHEM M07A, equivalent college course with a C or higher or
Course requires a lab coat and goggles. C-ID: CHEM 160S
II. COURSE OBJECTIVESUpon successful completion of the course, a student will be able to:
Methods of evaluation willbe consistent with, but not
limited by, the followingtypes or examples.
1
rank radicals in the correct order of stability, demonstrate (usingbond energy tables) which free-radical halogenations areendothermic and exothermic, write out initiation, propagation,and termination steps that occur in a free-radical reaction, andpredict which hydrogen is most likely to be substituted in analkane given the structure and nature of the halide involved.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
2
predict properties of ultraviolet-visible (UV-Vis) spectra ofconjugated dienes, explain how conjugation affects molecularorbitals and bond lengths in polyenes, predict the course ofelectrophilic addition to polyenes, and predict strength ofparticipation of dienes and dienophiles in Diels-Alder reactionsbased on molecular structure.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
3name aromatic compounds using both common names andIUPAC nomenclature system, generate Frost diagrams ofmolecular orbitals for ring systems, and use the latter to predictaromatic properties of these rings.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
4
classify various functional groups as either electron-donating orwithdrawing and predict their effects on the rates of electrophilicaromatic substitution (EAS) reactions, explain the factors thatcause meta- versus ortho/para- substitution in EAS reactions,and predict the course of nucleophilic aromatic substitution(SNAr) reactions based on mechanistic considerations.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
5
name carbonyl-containing compounds using common andsystematic naming schemes, utilize organometallic reagentsand hydride reducing reagents in synthetic schemes withvarious carbonyl groups, and predict whether a carbonyl willundergo nucleophilic addition or nucleophilic acyl substitutionbased on the nature of the substrate.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
predict the major organic product of nucleophilic additionreactions to aldehydes and ketones and contrast themechanisms and products produced with the use of hydride
6 reducing agents, organometallic reagents, Wittig reagents,primary and secondary amines, and alcohols as nucleophiles inthese reactions. Students should also be able to explain themechanism of mutarotation in carbohydrates and be able to useacetal protecting groups in organic synthesis schemes.
applications (includingwritten expression of resultsand conclusions), finalexaminations.
7predict the major organic product of nucleophilic acylsubstitution reactions of carboxylic acid derivatives and use aseries of these reactions to interconvert between carboxylicacids, acid chlorides, anhydrides, esters, and amides.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
8
utilize the mechanism of enolate formation to predict theproducts of reactions involving a-substitution of a carbonylgroup and propose synthetic schemes that utilize a-substitutionfollowed by subsequent decarboxylation (e.g., malonic estersynthesis, acetoacetic ester synthesis, etc).
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
9
predict the major organic products of aldol, crossed aldol, andintramolecular aldol reactions, identify the common problems ofcrossed aldol reactions and ways to alleviate them through theuse of pre-formed enolates, and show the mechanisticsimilarities between various name reactions such as theDieckmann cyclizations, Robinson annulations, Michaeladditions, Claisen condensations, and other enol-basedcondensations.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
10
name amine-containing compounds utilizing common andsystematic naming schemes, propose reaction pathways forsynthesis of amines, give examples of the reactions of amines,and identify common, commercially important alkaloids.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
11
predict which anomer of a carbohydrate is most stable,differentiate between reactions of anomeric alcohols and sidechain alcohols, use Fischer projections and Haworth diagramsto indicate stereochemistry of saccharides, and indicate howthe various anomeric linkages affect the structure andbiochemistry of polysaccharides.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
12
classify the amino acids by their acidity, by lipophilicity, identifyisoelectronic points based on pKa’s, draw the zwitterionic formsof the amino acids, show how solid phase synthesis is used toassemble large peptide chains, demonstrate knowledge ofcurrently used blocking and linking reagents, and identify theforces that affect the structure of enzymes and proteins.
quizzes, examinations,laboratory-basedapplications (includingwritten expression of resultsand conclusions), finalexaminations.
identify and categorize (e.g., wax, triacylglycerol, phospholipid,eicosanoid, vitamin, terpene, steroid, etc.) lipids based on
13 structure, identify isoprene units in terpenes, steroids and othernatural products, and provide speculative pathways ofbiosynthesis.
applications (includingwritten expression of resultsand conclusions), finalexaminations.
14
demonstrate safe laboratory practice while synthesizing organiccompounds by refluxing reactants, isolate these compoundsusing modern methods of purification, qualitatively andquantitatively determine the success of the reaction, recordresults in a properly formatted laboratory notebook, and reportresults.
utilize products synthesized and purified in a laboratoryenvironment in multi-step reaction sequences to producecomplex organic compounds from relatively simple startingmaterials, and utilize combined modern spectroscopictechniques to verify product identity and purity to determine thestructure of unknown compounds.
Radical Reactions:Initiation – propagation – termination mechanism and its use in thehalogenation of alkanes and allylic carbons and in radical addition todouble bonds.
1
6.00%Conjugation, Resonance, and Dienes:Conjugated dienes and polyenes, resonance and resonance hybrid,1,2- vs. 1,4-electrophilic addition, Diels-Alder reactions.
2
8.00%
Aromaticity:Nomenclature, origin of aromatic ring energy, molecular orbitals ofaromatic systems, Frost diagrams, anti-aromatic systems, andphysical properties of aromatic rings.
3
10.00%
Electrophilic Aromatic Substitution:Reactions of benzene with halogens, Friedel-Crafts reactions,nitrations and sulfonations, directing effects, rate effects, furtherreactions of sidechains, and nucleophilic aromatic substitution.
3
12.00%
Introduction to Carbonyl Chemistry:Nomenclature, nucleophilic addition versus nucleophilic acylsubstitution of carbonyl compounds, relative reactivity of carbonylcompounds, organometallic compounds and metal hydrides asnucleophiles, use of protecting groups.
Nucleophilic Addition to Aldehydes and Ketones:Nucleophilic addition of organometallic compounds, metal hydrides,cyanide, and primary and secondary amines, the Wittig reaction,(hemi)acetal formation, use of acetals as protecting groups, andmutarotation in carbohydrates.
6
8.00%
Nucleophilic Acyl Substitution of Carboxylic Acid & Derivatives:Single-step and multi-step intercoversion between carboxylic acids,acid chlorides, acid anhydrides, esters, and amides, along withreactions of nucleophiles with nitrile functional groups.
7
10.00%
Substitution Reactions of Carbonyl Compounds at a-Carbon:Formation and relative stability of enolates, halogenation andalkylation of enolate carbon, decarboxylation, malonic estersynthesis, and acetoacetic ester synthesis.
4.00%Amines:Nomenclature, basicity, Gabriel synthesis, tetraalkylammoniumsalts, reactions of amines, Hofmann elimination.
10
6.00%
Carbohydrates:Carbohydrate nomenclature, Fischer projections, mutarotation ofanomeric centers, polysaccharides, reactions of anomeric centers,reactions of side chains, biological consequences of saccharides.
11
6.00%
Amino Acids, Peptides, and Proteins:Structure and nomenclature of amino acids, synthesis and resolutionof amino acids, structure of peptides, analysis of peptide sequences,and biological properties of peptides and enzymes.
12
4.00%Lipids:Waxes, fats, oils, vitamins, biosynthesis of terpenes, steroids,prostaglandins, and phospholipids.
13
Lab (must total 100%)
20.00%
Spectroscopic Determination of Structure:Use of modern instrumentation (1H NMR, 13C NMR, IR, MS, etc.)to determine structures of compounds synthesized in lab and givenas challenge problems.
14, 15
30.00%
Single-Step Synthesis of Organic Compounds:“Standard-scale” and micro-scale synthesis, separation, purification,and characterization of organic compounds including thesetechniques: reflux, recrystallization, distillation, andchromatography. Keep lab notebooks, analyze and report results.
14, 15
50.00%
Multi-Step Synthesis of Organic Compounds:Synthesis of organic compounds with an emphasis placed on purityand yield of each reaction step so that student may carry the productforward to the next step of the reaction.
Methods of instruction may include, but are not limited to:
VI. METHODS OF EVALUATIONMethods of evaluation may include, but are not limited to:
Multi-week lab experiment with formal reportOnline homework with standardized grading through textbook publisher that allowscomparisons to national norms
VII. REPRESENTATIVE TEXTS AND OTHER COURSE MATERIALS
SpectroscopyOxnard College CHEM R132 Organic Chemistry II 5Ventura College CHEM V12B &
V12BLGeneral Organic Chemistry II & Lab 3/2
CSU East Bay CHEM 2301 &2302
Survey of Organic Chemistry & Survey ofOrganic Chemistry
4/4
CSU MontereyBay
CEHM 212 & 212L Organic Chemistry II and Lab 3/1
X. MINIMUM QUALIFICATIONSCourses Requiring a Masters Degree:Master’s in chemistry OR Bachelor’s in chemistry or biochemistry AND Master’s in biochemistry,chemical engineering, chemical physics, physics, molecular biology, or geochemistry OR theequivalent.
XI. ARTICULATION INFORMATIONA. Title V Course Classification:
1. This course is designed to be taken either:
Pass/No Pass only (no letter grade possible); orX Letter grade (P/NP possible at student option)
2. Degree status:Either X Associate Degree Applicable; or Non-associate DegreeApplicable
B. Moorpark College General Education:1. Do you recommend this course for inclusion on the Associate Degree
General Education list?Yes: X No: If YES, what section(s)?
A1 - Natural Sciences - Biological ScienceX A2 - Natural Sciences - Physical Science B1 - Social and Behavioral Sciences - American History/Institutions B2 - Social and Behavioral Sciences - Other Social Behavioral Science C1 - Humanities - Fine or Performing Arts C2 - Humanities - Other Humanities D1 - Language and Rationality - English Composition D2 - Language and Rationality - Communication and Analytical Thinking E1 - Health/Physical Education E2 - PE or Dance F - Ethnic/Gender Studies
C. California State University(CSU) Articulation:
1. Do you recommend this course for transfer credit to CSU? Yes: X No:
2. If YES do you recommend this course for inclusion on the CSU GeneralEducation list?Yes: X No: If YES, which area(s)?
1. Do you recommend this course for transfer to the UC? Yes: X No:
2. If YES do you recommend this course for the Intersegmental GeneralEducation Transfer Curriculum (IGETC)? Yes: X No:
IGETC Area 1: English Communication
English Composition Critical Thinking-English Composition Oral Communication
IGETC Area 2: Mathematical Concepts and Quantitative Reasoning
Mathematical Concepts
IGETC Area 3: Arts and Humanities
Fine Arts Humanities
IGETC Area 4: Social and Behavioral Sciences
Anthropology and Archaeology Economics Ethnic Studies Gender Studies Geography History Interdisciplinary, Social & Behavioral Sciences Political Science, Government & Legal Institutions Psychology Sociology & Criminology
IGETC Area 5: Physical and Biological Sciences (mark all that apply)
Physical Science Lab or Physical Science Lab only (none-sequence) Physical Science Lecture only (non-sequence) Biological Sciences Physical Science Courses Physical Science Lab or Biological Science Lab Only (non-
sequence) Biological Science Courses Biological Science Lab course First Science course is a Special sequence
1. describe how various organic molecules are used in medicine, industry,and the household and how their use impacts daily life and draw correctLewis structures for a wide variety of main-group compounds, identify hybridand molecular orbitals utilized in bonding, and convert formulas into variousthree dimensional structural representations including skeletal (bond-line)structures and resonance hybrids.
2. name cyclic and acyclic compounds containing alcohols, halides, alkenesand alkynes using the IUPAC system, name small compounds using common(e.g., iso, sec-, tert-) prefixes, identify and name compounds containingcommon functional groups such as halides, alkenes, alkynes, carbonyl groups,alcohols, amines, aromatic rings and ethers.
3. identify conformational isomers, draw Newman projections andcyclohexane chair forms that accurately portray axial and equatorial groups,and predict which Newman projection and chair form will be most stable andleast stable.
4. identify stereoisomers, label a stereocenter using the Cahn-Ingold-Prelogrules, distinguish between and define the terms enantiomer, diastereomer,meso, chiral and achiral, and provide examples of chiral molecules withoutstereocenters.
5. predict both the magnitude and direction of the polarity of organicmolecules, identify intermolecular forces between organic molecules, andunderstand how intermolecular forces influence boiling point, solubility,nucleophilicity, and reactivity of organic compounds.
X
Second Science course in a Special SequenceX Laboratory ActivityX Physical Sciences
IGETC Area 6: Language other than English
Languages other than English (UC Requirement Only) U.S. History, Constitution, and American Ideals (CSU
Requirement ONLY)
XII. REVIEW OF LIBRARY RESOURCESA. What planned assignment(s) will require library resources and use?
The following assignments require library resources:Readings, from the Library's print and online resources, of newspaper andscholarly journal articles on topics appropriate to organic chemistry.
B. Are the currently held library resources sufficient to support the courseassignment?
YES: X NO:
If NO, please list additional library resources needed to support this course.
XIII. PREREQUISITE AND/OR COREQUISITE JUSTIFICATIONRequisite Justification for CHEM M07A
6. predict the course of any acid-base reaction based on pKa values andorganic structures, rank common functional groups in order of their pKavalues, draw “electron arrows” to indicate the flow of electrons in Lewis acid-base reactions, and identify various reagents that will quantitativelydeprotonate an alcohol and an alkyne.
7. draw the mechanism and predict the products of inter- and intramolecularnucleophilic substitution (SN) reactions, including stereocenter inversionduring an SN2 reaction, racemization of stereochemistry during an SN1reaction, and carbocation rearrangements. Students should be able to rankcarbocations in the correct order of stability and list various groups in order oftheir nucleophilicity and use these skills to rank the rate of similar SNreactions that vary in the nature of the substrate.
8. use Zaitsev’s rule to predict which alkenes will be most stable, labelalkenes as E or Z using the Cahn-Ingold-Prelog rules, predict whether a givennucleophile will give predominately elimination or substitution in a reaction,draw the mechanisms of E2 and E1 reactions, and use this information topredict the major and minor products of substitution and elimination reactionsof electrophiles bearing a leaving group.
9. draw the mechanism and predict the products of addition reactions toalkenes and alkynes including reactions that demonstrate the stereochemicalramifications of the addition of halogens and hydrohalogens (in the presenceand absence of water), the difference between acid-catalyzed hydration andhydroboration as methods of adding hydroxy groups, and the consequences oftautomerization to the enol products formed during hydration of alkynes.
10. draw the mechanism and predict the products of redox reactions ofalkenes and alkynes, including epoxidation, stereoselective dihydroxylation,ozonolysis, catalytic hydrogenation, and stereoselective reduction of alkynesto cis and trans alkenes. Also, plan synthetic strategies using alkynylnucleophiles.
11. draw the mechanism and predict the products of substitution, elimination,and redox reactions of alcohols, ethers, and epoxides, including theWilliamson ether synthesis, dehydration reactions catalyzed by acids andother reagents, conversions of alcohols to alkyl halides using hydrohalogensand other reagents, tosylate formation, oxidations of alcohols to formaldehydes, carboxylic acids, and ketones, acid-catalyzed decomposition ofethers, and the stereochemical ramifications of epoxide-opening reactions inthe presence and absence of acid catalysts.
12. explain the use of infrared spectroscopy and mass spectrometry in thedetermination of organic chemical structure, identify specific functionalgroups from IR spectral data, and use IR and MS data to make determinationsabout organic structures.
13. identify the causes and origins of the nuclear magnetic resonance (NMR)effect, correlate chemical shifts in NMR spectra with structure and predict theintegrations, positions and peak splitting of signals in proton spectroscopy,and be able to both predict the NMR spectra given structure of compoundsand to deduce their structure based on spectral data.
14. separate and purify compounds using recrystallizations, simple,fractional, and steam distillations, extractions (including acid-baseextractions), filtrations, and chromatography (including gas chromatography,GC, and thin layer chromatography, TLC) and determine purity and identityof samples through the use of melting point, infrared spectroscopy, and NMRspectroscopy.
15. demonstrate safe laboratory practice while synthesizing organiccompounds by refluxing reactants, isolate these compounds, qualitatively andquantitatively determine the success of the reaction, record results in aproperly formatted laboratory notebook, and report results.
B. Standard Prerequisite or Corequisite required by universities.
C. Corequisite is linked to companion lecture course.
D. Prerequisite or Corequisite is authorized by legal statute or regulation.Code Section:
E. Prerequisite or Corequisite is necessary to protect the students' healthand safety.
F. Computation or communication skill is needed.
G. Performance courses: Audition, portfolio, tryouts, etc. needed.
A. Sequential course within a discipline.
B. Standard Prerequisite or Corequisite required by universities.
C. Corequisite is linked to companion lecture course.
D. Prerequisite or Corequisite is authorized by legal statute or regulation.Code Section:
E. Prerequisite or Corequisite is necessary to protect the students' healthand safety.
F. Computation or communication skill is needed.
Requisite Justification for equivalent college course with a C or higher
G. Performance courses: Audition, portfolio, tryouts, etc. needed.
or
XIV. WORKPLACE PREPARATIONCHEM M07B: Not Applicable
XV. DISTANCE LEARNING COURSE OUTLINE ADDENDUM1. Mode of Delivery
Online (course will be delivered 100% online)
Online with onsite examinations (100% of the instruction will occuronline, but examinations and an orientation will be scheduled onsite)
X Online/Hybrid (a percentage of instruction will be held online and theremaining percentage of instruction will be held onsite)
X Lab activities will be conducted onsite
Televideo (Examinations and an orientation will be held onsite)
Teleconference
Other
2. Need/Justification
Improve general student access.
3. Describe how instructors teaching this course will ensure regular, effective contactwith and among students.
Synchronous and asynchronous contact will be maintained with students throughonline live classroom presentations, discussion board and chat room interactions,and weekly onsite lectures and laboratory sessions.
4. Describe how instructors teaching this course will involve students in activelearning.
This course will be taught with 40% onsite and 60% online. The onsite consists ofthe college technological platform and overall course introduction, three to fourwritten examinations plus cumulative final exam, hands-on laboratories, andmultiple discussion sections. The online consists of discussion board and chatroom interactions, possible virtual lab demonstrations, and class-wide emails aswell as individual student emails to maintain a constant ambience of activelearning.
5. Explain how instructors teaching this course will provide multiple methods ofcontent representation.
Students will have access to all lecture notes and are responsible for printing theseprior to class for notetaking. Students will learn onsite through initial courseorientation, learn about the selected college-wide technological platform and itsusage in the course, take three to four examinations plus the cumulative finalexam, and conduct all labs onsite. Instructors may also choose to include audioand video files to supplement lecture material online.
6. Describe how instructors teaching this course will evaluate student performance.
Student grades will be evaluated similar to a traditionally taught course. Forexample: quizzes (20%), online participation and discussion questions (10%),examinations (50%), and laboratory experiment reports (20%).
XVI. General Education Course Outline AddendumGeneral Education Division of Learning [check all applicable boxes]:
X Natural Sciences
Biological Science
X Physical Science
Social and Behavioral Sciences
American History/Institutions
Other Social Science
Humanities
Fine or Performing Arts
Other Humanities
Language and Rationality
English Composition
Communication and Analytical Thinking
Health/Physical Education
Ethnic/Women's Studies
Check either Option 1 or Option 2
XVII. Student Materials Fee AddendumCHEM M07B: Not Applicable
XVIII. Repeatability Justification Title 5, Section 55041CHEM M07B: Not Applicable
XIX. CURRICULUM APPROVALA. Course Information:
1. Discipline: CHEMISTRY
2. Discipline Code and Number: CHEM M07B
3. Course Revision Category: Outline Update
X OPTION #1: Moorpark College has already received approval from theCSU and/or UC systems for this course to fulfill a GE requirement. Note:This option applies only to technical revisions and updated courses.
OPTION #2: Moorpark College has not received approval from the CSUand/or UC systems for this course to fulfill a GE requirement. This optionapplies to all new and substantively revised courses.
