Organic Chemistry 1 | Madison College Outline of Instruction

20806213 Organic Chemistry 1

Course Information

Description

The first semester of a two-semester organic chemistry sequence. Includes the electronic structure and bonding of atoms and molecules; the nomenclature, mechanisms, reactions and properties of the following classes of compounds - alkanes, alkenes, alkynes, alkyl halides, alcohols, ethers, thiols, and sulfides; instrumental (IR, NMR) methods of analysis and their interpretation. Includes a three hour per week laboratory component as well as four hours per week lecture/discussion.

Total Credits

Course Competencies (Course Outcomes)

Explain the characteristics of atoms that relate to chemical bonding

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write and interpret electronic configurations

you write and interpret electron dot symbols

you recognize electronegativity trends in the periodic table

you recognize atomic radius trends in the periodic table

you identify the number of covalent bonds that nonmetallic elements usually form

you identify atomic orbitals

you recognize the differences between ionic and covalent bonds

you calculate the formal charge on an atom or ion

you recognize the importance of electronegativity and polarizability in the formation of polar covalent bonds
Explain the characteristics of molecules that relate to chemical bonding

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you predict the types of bonds for a compound formed from specific atoms

you predict the formula for a compound formed from specific atoms

you write Lewis and line bond structures for molecules

you use arrow and half-arrow (fishhook) symbols to show the movement of electrons

you use both the crossed arrow and delta symbols to represent a polar bond

you identify the properties of sigma and covalent bonds
Explain the characteristics of molecules that relate to physical properties

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you compare the following intermolecular forces: dipole-dipole interactions, London forces, hydrogen bonding

you relate intermolecular forces to solubility characteristics of molecules

you relate intermolecular forces to boiling points of molecules

you relate intermolecular forces to shapes of molecules
Compare acid-base properties of organic compounds

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you identify the properties of strong acids

you identify the properties of strong bases

you identify the properties of weak acids

you identify the properties of weak bases

you calculate and interpret the meaning of Ka

you calculate and interpret the meaning of Kb

you calculate and interpret the meaning of pKa

you calculate and interpret the meaning of pKb

you write the formulas for conjugate acids

you write the formulas for conjugate bases

you summarize the strength relationship of conjugate acid-base pairs

you identify the characteristics of acids and bases in the Arrhenius theory

you identify the characteristics of acids and bases in the Bronsted-Lowry theory

you identify the characteristics of acids and bases in the Lewis theory

you identify organic acid functional groups

you identify organic base functional groups
Explain the role of orbitals in chemical bonding

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you identify the properties of sigma and pi covalent bonds

you complete a molecular orbital diagram

you identify the hybridization and geometries of atoms in molecules or ions

you relate resonance to the characteristics of benzene

you write resonance forms

you identify resonance forms as major or minor contributors
Explain the characteristics of molecules that relate to their orbital interactions

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you identify orbitals involved in bonds

you relate hybridization to bond length

you identify functional groups

you identify and use the symbolism -R (alkyl)

you identify and use the symbolism -Ar (aryl)

you identify the polarity and bonding in a carbonyl group

you identify conjugated double bond systems in a molecule

you identify cumulative double bond systems in a molecule

you identify isolated double bond systems in a molecule

you explain how conjugated systems allow for delocalization of electrons

you use appropriate symbols to represent resonance structures

you relate resonance to the acidity of organic compounds
Interpret different types of chemical formulas Linked Core Abilities

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write and interpret the following for molecules: Lewis structures

you write and interpret the following for molecules: molecular formula

you write and interpret the following for molecules: empirical formula

you write and interpret the following for molecules: complete structural formula

you write and interpret the following for molecules: condensed formula

you write and interpret the following for molecules: skeletal formula

you write and interpret the following for molecules: line angle formula

you interpret the following for molecules: 3-dimensional representations of types:
Predict products for alkane reactions

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write halogenation reactions for saturated hydrocarbons

you write combustion reactions for saturated hydrocarbons
Determine physical properties of hydrocarbons

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you identify the trends in solubility for alkanes and cycloalkanes

you identify the trends in boiling point for alkanes and cycloalkanes

you identify the trends in density for alkanes and cycloalkanes
Identify the names and formulas for alkanes, cycloalkanes and substituted alkanes

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you identify structures of isomers

you draw the structures of isomers

you write the correct names for alkanes

you write the correct names for cycloalkanes

you write the correct names for cycloalkanes derivatives

you draw correct structures for organic compounds (alkanes, cycloalkanes, alkyl halides)

you name and/or draw the structure for the methylene group

you name and/or draw the structure for the phenyl group

you name and/or draw the structure for the benzyl groups

you name and/or draw the structure for the nitro group

you name and/or draw the structure for the chloro group

you name and/or draw the structure for the bromo groups

you name and/or draw the structure for the iodo group

you name and/or draw the structure for the fluoro group

you name and/or draw the structure for the methyl group

you name and/or draw the structure for the ethyl group

you name and/or draw the structure for the propyl group

you name and/or draw the structure for the butyl group
Determine the stereochemistry of organic compounds

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write and interpret 3-dimensional structures using wedge/dash

you write and interpret 3-dimensional structures using sawhorse

you write and interpret 3-dimensional structures using Fischer projections

you write and interpret 3-dimensional structures using Newman projections

you identify molecules that are: cis or trans; E or Z; R or S

you use Newman projections to relate conformations to energy in molecules

you relate heat of combustion data to the concept of ring strain

you write conformations for small cycloalkanes

you identify axial and equatorial positions on cyclohexane

you identify chiral carbons and their relationship to enantiomers

you identify chiral carbons and their relationship to diastereomers

you identify chiral carbons and their relationship to meso forms

you explain how a polarimeter functions and the type of information it provides

you use appropriate symbolism to indicate an optically active compound

you summarize formulas for chiral compounds

you summarize ways to resolve racemic mixtures

you explain the concept of prochirality
Determine the stereochemistry of substitution and elimination reactions

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you explain the stereochemical factors in SN1 reactions

you explain the stereochemical factors in SN2 reactions

you explain the stereochemical factors in E1 reactions

you explain the stereochemical factors in E2 reactions
Summarize the steps in substitution and elimination mechanisms

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you draw and interpret energy diagrams for substitution and elimination reactions

you explain the kinetics of substitution and elimination reactions

you write mechanisms for substitution and elimination reactions

you predict products of hydride and alkide shifts

you explain the rates of allylic and benzylic reactions

you explain the kinetic isotope effect
Predict products of substitution and elimination reactions

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you summarize reactants and products for substitution and elimination reactions

you indicate trends in halogens as leaving groups

you identify factors that lead to substitution and elimination reactions

you compare nucleophilicity and basicity

you identify factors that affect the rate of substitution and elimination reactions

you predict Saytzeff/Hofmann ratios of products in elimination reactions

you predict cis/trans ratios of products in elimination reactions
Determine physical properties of alkyl halides

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you identify the trends in solubility for halogenated alkanes

you identify the trends in boiling point for halogenated alkanes

you identify the trends in density for halogenated alkanes
Identify the names and formulas for alkyl halides

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write correct names for alkyl halides

you draw correct structures for alkyl halides

you summarize alkyl halides

you summarize ary halides

you summarize vinyl halides

you summarize methy halides

you summarize primary halides

you summarize secondary halides

you summarize tertiary halides
Predict products for free radical reactions

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you predict the product(s) of free radical substitution reactions of chlorine

you predict the product(s) of free radical substitution reactions of bromine

you identify the relative reactivities of chlorine in free radical reactions

you identify the relative reactivities of bromine in free radical reactions

you write products of NBS with alkenes

you summarize products of pyrolysis reactions and reactions of alkenes with oxygen

you predict monomer and/or polymer structures
Summarize the mechanisms for free radical reactions

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write initiation, propagation and termination steps of individual and polymerization reactions

you summarize the relative stability of free radical intermediates

you show peroxides as free radical initiators

you show phenols as free radical inhibitors

you write resonance structures for free radical intermediates
Determine the stereochemistry of free radical reactions

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you explain the stereochemistry of free radical reactions
Compare acid-base properties of alcohols

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you show alcohols as acids and bases
Outline mechanisms for reactions of alcohols

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you outline the Grignard/organolithium reactions with carbonyl compounds mechanism

you outline the hydrogen halides with alcohols mechanism

you outline the tosylate esters with nucleophiles mechanism

you outline the thionyl chloride with alcohols mechanism

you outline the dehydration of alcohols mechanisms
Predict products of alcohol reactions

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you draw products for the following reactions of alcohols with: halides, thionyl chloride, phosphorus tribromide, acids, oxidizing agents, reducing agents

you draw products for the reaction of alcohols with halides

you draw products for the reaction of alcohols with thionyl chloride

you draw products for the reaction of alcohols with phosphorus tribromide

you draw products for the reaction of alcohols with acids

you draw products for the reaction of alcohols with oxidizing agents

you draw products for the reaction of alcohols with reducing agents

you summarize the relative reactivities of hydrogen halides with alcohols

you solve synthesis problems involving alcohols

you identify oxidation and reduction in organic reactions
Determine physical properties of alcohols

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you relate hydrogen bonding to the solubility of alcohols

you relate hydrogen bonding to the boiling point of alcohols
Write names and formulas for alcohols

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write the correct names for alcohols and diols

you write the correct structures for alcohols and diols

you identify alcohols as primary, secondary, and tertiary
Outline methods to synthesize alcohols

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you predict products for the reaction of alkyl halides and hydroxide

you predict products for the reaction of reduction of carbonyl compounds

you predict products for the reaction of hydration of alkenes

you predicts products for the reaction of Grignard and Lithium reagents with carbonyl compounds, water

you predicts products for the reaction of alkyl halides and magnesium or lithium
Compare acid-base properties of ethers, epoxides, and sulfides

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you compare the acidity of alcohols and thiols
Outline mechanisms for reaction of ethers, epoxides, and sulfides

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you indicate mechanisms for the following reactions: Williamson ether synthesis

you indicate mechanisms for the following reactions: alkene + peroxyacid

you indicate mechanisms for the following reactions: intramolecular reaction of halohydrins

you indicate mechanisms for the following reactions: epoxide cleavage with acid and/or base

you indicate mechanisms for the following reactions: ethers and HI and/or HBr

you indicate mechanisms for the following reactions: sulfides by SN2
Predict products of ethers, epoxides, and sulfide reactions

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write reactants, products, conditions for the following reactions :ethers and HBr or HI

you write reactants, products, conditions for the following reactions: acid/base catalyzed cleavage of ethers

you write reactants, products, conditions for the following reactions: Grignard + epoxide

you write reactants, products, conditions for the following reactions: Williamson ether synthesis

you write reactants, products, conditions for the following reactions: intermolecular dehydration of alcohols

you write reactants, products, conditions for the following reactions: thiol + strong base

you write reactants, products, conditions for the following reactions: alkyl halide + bisulfide.

you write reactants, products, conditions for the following reactions: alkyl halide + alkyl sulfide

you write reactants, products, conditions for the following reactions: oxidation of thiols and sulfides

you write reactants, products, conditions for the following reactions: reduction of disulfides.
Determine physical properties of ethers, epoxides, and sulfides

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you summarize the trends in solubility for ethers and sulfur containing organic compounds

you summarize the trends in boiling point for ethers and sulfur containing organic compounds

you summarize the trends in density for ethers and sulfur containing organic compounds

you relate hydrogen bonding to the solubility of ethers and sulfur containing organic compounds

you relate hydrogen bonding to the boiling point of ethers and sulfur containing organic compounds
Write names and formulas for ethers, epoxides, and sulfides

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write the correct names for ethers

you write the correct names for epoxides

you write the correct names for oxiranes

you write the correct names for thiols

you write the correct names for sulfides

you draw the correct structure for ethers

you draw the correct structure for epoxides

you draw the correct structure for oxiranes

you draw the correct structure for thiols

you draw the correct structure for sulfides
Outline methods to synthesize ethers, epoxides, and sulfides

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write the reactants, products and conditions for the following reaction: dehydration of alcohols

you write the reactants, products and conditions for the following reaction: Williamson ether synthesis

you write the reactants, products and conditions for the following reaction: alkene + peroxyacid

you write the reactants, products and conditions for the following reaction: intramolecular reaction of halohydrins
Interpret IR and NMR spectra

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you identify major functional groups in spectra

you explain the effects of hydrogen bonding

you explain the shielding effects

you explain the inductive and anisotropic effects

you identify chemically equivalent hydrogens

you identify relative areas

you identify splitting patterns

you identify compounds that produce spectra for IR

you identify compounds that produce spectra for proton NMR

you identify compounds that produce spectra for carbon-13 NMR

you calculate unsaturation number (double bond equivalents) for a compound
Explain the theory of IR and NMR

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you explain the relationship of energy, wavelength, frequency

you identify IR vibrational states

you explain how IR and NMR instruments work

you relate magnetic states of nuclei to NMR
Compare acid-base properties of alkenes and alkynes

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you compare the relative acidity of a terminal alkyne with other organic functional groups
Summarize the mechanisms for reactions of alkenes and alkynes

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you outline the mechanisms for the following reaction: addition of acids to alkenes

you outline the mechanisms for the following reaction: Markovnikov and anti-Markovnikov

you outline the mechanisms for the following reaction: oxymercuration-demercuration

you outline the mechanisms for the following reaction: hydroboration, carbene addition;

you outline the mechanisms for the following reactions: Simmons-Smith reaction

you draw energy diagrams to explain: Markovnikov addition; effect of a catalyst
Predict products of reactions of alkenes and alkynes

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you indicate reactants, products and conditions for the following reaction: terminal alkyne + sodamide and/or Grignard

you indicate reactants, products and conditions for the following reaction: addition of acids, halogens, hydrogen to alkenes and alkynes

you relate heats of hydrogenation to alkene stability

you indicate products and conditions for the reaction of alkenes and alkynes with potassium permanganate

you indicate products and conditions for the reaction of alkenes and alkynes with osmium tetroxide

you indicate products and conditions for the reaction of alkenes and alkynes with sodium bisulfite

you indicate products and conditions for the reaction of alkenes and alkynes with peroxycarboxylic acids

you indicate products and conditions for the reaction of alkenes and alkynes with oxygen

you indicate products and conditions for the reaction of alkenes and alkynes with ozone
Determine physical properties of alkenes and alkynes

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you summarize the trends in solubility for alkenes and alkynes

you summarize the trends in boiling point for alkenes and alkynes

you summarize the trends in density for alkenes and alkynes
Identify the names and formulas for alkenes and alkynes

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you write correct names for alkenes and alkynes

you draw correct structures for alkenes and alkynes
Summarize the methods to synthesize alkenes and alkynes

Assessment Strategies

with a minimum score of 70% on written exams and quizzes

without referring to text and/or other reference material

with periodic table and other tables and/or charts as provided

Criteria

you use the E2 reaction of alkyl halides and vicinal dihalides method to synthesize alkenes and alkynes

you use the acetylides + alkyl halides method to synthesize alkenes and alkynes

you use the Grignard + carbonyl compound method to synthesize alkenes and alkynes
Prepare organic compounds

Assessment Strategies

in the lab

with a minimum score of 70% on laboratory reports

Criteria

you outline methods to synthesize different organic compounds

you use methods to isolate and purify organic compounds
Demonstrate proper safety skills

Assessment Strategies

in the lab

following safety procedures

Criteria

you use proper safety skills during the laboratory experience
Demonstrate proper laboratory skills

Assessment Strategies

in the lab

with a minimum score of 70% on laboratory reports

Criteria

you identify organic compounds

you set up equipment properly

you write up laboratory reports properly