Organic Chemistry 2 | Madison College Outline of Instruction

20806214 Organic Chemistry 2

Course Information

Description

Continuation of Organic Chemistry 1. Includes the theory and interpretation of NMR and UV-VIS spectrophotometry; the nomenclature, mechanisms, reactions and properties of the following classes of compounds alkadienes, aromatic, aldehydes, ketones, enols/enolates, carboxylic acids, carboxylic acid derivatives, amines, aryl halides, and phenols. Includes a three hour per week laboratory component as well as four hours per week lecture/discussion.

Total Credits

Course Competencies (Course Outcomes)

Summarize the names and formulas for simple aromatic 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 the correct names for substituted benzene compounds

you draw the correct structures for substituted benzene compounds
Determine physical properties of aromatic 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 summarize the trends in solubility for aromatic compounds

you summarize the trends in boiling point for aromatic compounds

you summarize the trends in density for aromatic compounds
Predict products of aromatic 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 the reactants, products, conditions for halogenation aromatic reactions

you write the reactants, products, conditions for Friedel-Crafts alkylation aromatic reactions

you write the reactants, products, conditions for Friedel-Crafts acylation aromatic reactions

you write the reactants, products, conditions for alkenes aromatic reactions

you write the reactants, products, conditions for nitration aromatic reactions

you write the reactants, products, conditions for sulfonation aromatic reactions

you identify the groups that are ortho-para directing

you identify groups that are meta directing

you identify groups that are activating

you identify groups that are deactivating

you relate the stability of benzene to heat of hydrogenation data
Summarize the mechanisms for reactions of aromatic 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 outline the mechanism for electrophilic aromatic substitution
Identify spectral characteristics of aromatic 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 characteristics of aromatic compounds in NMR

you identify characteristics of aromatic compounds in IR
Explain the bonding in aromatic 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 compare resonance and molecular orbital interpretations of aromatic compounds

you identify characteristics of aromatic compounds

you identify characteristics of aromatic ions
Summarize the methods to synthesize substituted aromatic 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 the reactants, products and conditions for Sandmeyer reactions of aryl diazonium salts

you write the reactants, products and conditions for KI reactions of aryl diazonium salts

you write the reactants, products and conditions for HBF4 reactions of aryl diazonium salts

you write the reactants, products and conditions for water reactions of aryl diazonium salts

you write the reactants, products and conditions for hypophosphorous acid reactions of aryl diazonium salts

you write the reactants, products and conditions for activated aromatic rings reactions of aryl diazonium salts

you write the reactants, products and conditions for the nucleophilic reactions of aryl halides with ammonia

you write the reactants, products and conditions for the nucleophilic reactions of aryl halides with hydroxide

you write the reactants, products and conditions for the nucleophilic reactions of aryl halides with water

you write the reactants, products and conditions for synthesis of benzyne reactions

you write the reactants, products and conditions for benzyne reactions

you write the reactants, products and conditions for ammonia reactions
Predict products of reactions of substituted aromatic 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 the reactants, products and conditions for given compound with strong base reactions of phenols

you write the reactants, products and conditions for given compound with acids reactions of phenols

you write the reactants, products and conditions for given compound with anhydrides reactions of phenols

you write the reactants, products and conditions for given compound with acyl halides reactions of phenols

you write the reactants, products and conditions for reactions of phenols

you write the reactants, products and conditions for oxidation reactions of phenols

you write the reactants, products and conditions for oxidation of alkyl side chains reactions

you write the reactants, products and conditions for halogenation at benzylic positions reactions

you write the reactants, products and conditions for nitrous acid and aminobenzenes reactions

you write the reactants, products and conditions for reduction of aromatic nitro groups reactions
Summarize the mechanisms for reactions of substituted aromatic 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 indicate the mechanism for the nucleophilic substitution reaction of aryl halides
Compare acid-base properties of phenols with other 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 compare the acidity of phenols with water

you compare the acidity of phenols with other organic compounds
Summarize the names and formulas for aldehydes and ketones

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 aldehydes

you write the correct names for ketones

you draw the correct structure for aldehydes

you draw the correct structure for ketones
Determine physical properties of aldehydes and ketones

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 aldehydes

you summarize the trends in solubility for ketones

you summarize the trends in boiling point for aldehydes

you summarize the trends in boiling point for ketones

you summarize the trends in density for aldehydes

you summarize the trends in density for ketones
Predict products of aldehyde and ketone 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 the reactants, products, conditions for water reactions of aldehydes and ketones

you write the reactants, products, conditions for alcohols reactions of aldehydes and ketones

you write the reactants, products, conditions for HCN reactions of aldehydes and ketones

you write the reactants, products, conditions for Grignard reagents reactions of aldehydes and ketones

you write the reactants, products, conditions for addition-elimination reactions of aldehydes and ketones

you write the reactants, products, conditions for oxidation reactions of aldehydes and ketones

you write the reactants, products, conditions for reduction reactions of aldehydes and ketones
Summarize the methods to synthesize aldehydes and ketones

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, conditions for oxidation of alcohol reactions that produce aldehydes and ketones

you write the reactants, products, conditions for alkynes + water reactions that produce aldehydes and ketones

you write the reactants, products, conditions for the Friedel-Crafts acylation that produce aldehydes and ketones
Explain the mechanisms for reaction of aldehydes and ketones

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 keto-enol tautomerism

you indicate mechanisms for alpha halogenation of aldehydes/ketones

you indicate mechanisms for addition reactions of aldehydes/ketones

you indicate mechanisms for addition-elimination reactions of aldehydes/ketones
Compare acid-base properties of aldehydes and ketones

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 alpha hydrogens to other acidic organic compounds
Identify spectral characteristics of aldehydes and ketones

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 characteristics of aldehydes and ketones in NMR

you identify characteristics of aldehydes and ketones in IR
Summarize names and formulas for carboxylic acids

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 carboxylic acids

you draw the correct structures of carboxylic acids
Determine physical properties of carboxylic acids

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 carboxylic acids

you summarize the trends in boiling point for carboxylic acids

you summarize the trends in density for carboxylic acids

you relate hydrogen bonding to the solubility of carboxylic acids

you relate hydrogen bonding to the boiling point of carboxylic acids
Identify spectral characteristics of carboxylic acids

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 characteristics of carboxylic acids in NMR

you identify characteristics of carboxylic acids in IR
Explain the methods to synthesize carboxylic acids

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 hydrolysis of nitriles and acyl derivatives reactions to synthesize carboxylic acids

you write the reactants, products and conditions for oxidation of alcohols reactions to synthesize carboxylic acids

you write the reactants, products and conditions for alkenes reactions to synthesize carboxylic acids

you write the reactants, products and conditions for alkylbenzenes reactions to synthesize carboxylic acids

you write the reactants, products and conditions for Grignard + CO2 reactions to synthesize carboxylic acids
Predict products of carboxylic acid 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 the reactants, products, conditions for reactions with bases and carboxylic acids

you write the reactants, products, conditions for reactions with alcohols and carboxylic acids

you write the reactants, products, conditions for reactions with reducing agents and carboxylic acids

you write the reactants, products, conditions for reactions with beta-decarboxylation and carboxylic acids

you write the reactants, products, conditions for reactions with anhydride formation and carboxylic acids
Compare acid-base properties of carboxylic acids

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 carboxylic acids with other acidic organic compounds
Explain mechanisms for reactions of carboxylic acids

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 the mechanism for an esterification reaction
Summarize names and formulas for carboxylic acid derivatives

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 name for acyl halides

you write the correct name for acid anhydrides

you write the correct name for esters

you write the correct names for amides

you write the correct names for nitriles

you write the correct name for lactams

you write the correct name for imides

you write the correct name for carbamates (urethanes), sulfonamides

you write the correct name for sulfonamides

you draw correct structure for acyl halides

you draw correct structure for acid anhydrides

you draw correct structure for esters

you draw correct structure for nitriles

you draw correct structure for lactams

you draw correct structure for imides

you draw correct structure for carbamates (urethanes)

you draw correct structure for sulfonamides

you draw correct structure amides
Compare acid-base properties of carboxylic acid derivatives

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 basicity of amides and nitriles to other basic organic compounds
Explain the mechanisms for reaction of carboxylic acid derivatives

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 addition-elimination mechanism for carboxylic acid derivatives
Identify spectral characteristics of carboxylic acid derivatives

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 characteristics of carboxylic acid derivatives in NMR

you identify characteristics of carboxylic acid derivatives in IR
Explain the methods to synthesize carboxylic acid derivatives

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 reactions for the synthesis of acid halides: acid + thionyl chloride or phosphorus trihalides

you write the reactants, products and conditions for the following reaction for the synthesis of acid anhydrides: acyl halide + carboxylate salt

you write the reactants, products and conditions for the following reaction for the synthesis of acid anhydrides: two acids

you write the reactants, products and conditions for the following reaction for the synthesis of esters: alcohol + acid

you write the reactants, products and conditions for the following reaction for the synthesis of esters: acid hali-e

you write the reactants, products and conditions for the following reaction for the synthesis of esters: acid anhydride

you write the reactants, products and conditions for the following reaction for the synthesis of esters: ester

you write the reactants, products and conditions for the following reaction for the synthesis of nitriles: alkyl halide + cyanide

you write the reactants, products and conditions for the following reaction for the synthesis of nitriles: Sandmeyer reaction

you write the reactants, products and conditions for the following reaction for the synthesis of nitriles: dehydration of amides

you write the reactants, products and conditions for the synthesis of polyesters and polyamides
Predict products of carboxylic acid derivatives

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, conditions for the reaction of acid halides with water

you write the reactants, products, conditions for the reaction of acid halides with alcohols

you write the reactants, products, conditions for the reaction of acid halides with ammonia or amines

you write the reactants, products, conditions for the reaction of acid halides with aromatic compounds

you write the reactants, products, conditions for the reaction of acid halides with Grignard reagents

you write the reactants, products, conditions for the reaction of acid halides with reducing agents

you write the reactants, products, conditions for the reaction of acid halides with halogens

you write the reactants, products, conditions for the reaction of acid halides with carboxylate salts

you write the reactants, products, conditions for the reaction of acid anhydrides with water

you write the reactants, products, conditions for the reaction of acid anhydrides with alcohols

you write the reactants, products, conditions for the reaction of acid anhydrides with ammonia or amines

you write the reactants, products, conditions for the reaction of esters with water

you write the reactants, products, conditions for the reaction of esters with alcohol

you write the reactants, products, conditions for the reaction of esters with ammonia or amines

you write the reactants, products, conditions for the reaction of esters with reducing agents

you write the reactants, products, conditions for the reaction of esters with Grignard reagents

you write the reactants, products, conditions for the reaction of amides with water

you write the reactants, products, conditions for the reaction of amides with reducing agents

you write the reactants, products, conditions for the reaction of nitriles with water

you write the reactants, products, conditions for the reaction of nitriles with reducing agents
Explain the mechanisms for conjugated dienes and enones

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 mechanisms for the following reactions: 1,2 and 1,4 addition to a conjugated diene

you outline mechanisms for the following reactions: 1,4 additions to alpha, beta unsaturated carbonyl compounds

you outline mechanisms for the following reactions: Diels-Alder
Predict the reactants, conditions and products for diene and enone 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 reactants, conditions and products for the following: Diels-Alder reaction

you predict the reactants, conditions and products for the following: additions to alpha, beta unsaturated carbonyl compounds
Explain the mechanisms for enolate and carbanion 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 indicate mechanisms for the following enolate and carbanion reactions reaction: alkylation

you indicate mechanisms for the following enolate and carbanion reactions reaction: condensation
Predict products of enolate and carbanion 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 the reactants, products, conditions for the malonic ester synthesis alkylation reaction

you write the reactants, products, conditions for the acetoacetic ester synthesis alkylation reaction

you write the reactants, products, conditions for the alkylation of other carbonyl compounds alkylation reaction

you write the reactants, products, conditions for the alkylation (acylation) of enamines alkylation reaction

you write the reactants, products, conditions for the aldol and crossed aldol condensation carbanion reaction

you write the reactants, products, conditions for the Claisen and crossed Claisen condensation carbanion reaction; Michael addition; Robinson annulation

you write the reactants, products, conditions for the Michael addition carbanion reaction
Summarize the names and formulas for amines

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 amines

you write the correct names for ammonium salts

you draw the correct structures of amines

you draw the correct structures of ammonium salts
Determine physical properties of amines

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 amines and ammonium salts

you summarize the trends in boiling point for amines and ammonium salts

you summarize the trends in density for amines and ammonium salts

you relate hydrogen bonding to the solubility of amines

you relate hydrogen bonding to the boiling point of amines
Identify spectral characteristics of amines

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 characteristics of amines in NMR

you identify characteristics of amines in IR
Explain the methods to synthesize amines

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 reactions to synthesize amines: ammonia + alkyl halide

you write the reactants, products and conditions for the following reactions to synthesize amines: Gabriel synthesis

you write the reactants, products and conditions for the following reactions to synthesize amines: reduction of nitro compounds

you write the reactants, products and conditions for the following reactions to synthesize amines: nitriles

you write the reactants, products and conditions for the following reactions to synthesize amines: amides

you write the reactants, products and conditions for the following reactions to synthesize amines: reductive amination

you write the reactants, products and conditions for the following reactions to synthesize amines: Hofmann rearrangement
Predict products of amine 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 the reactants, products, conditions for the following reaction of amines with acids

you write the reactants, products, conditions for the following reaction of amines with enzenesulfonyl chloride

you write the reactants, products, conditions for the following reaction of amines with nitrous acid

you write the reactants, products, conditions for the following reaction of ammonium salts with base

you write the reactants, products, conditions for the following reaction of ammonium salts with silver oxide

you write the reactants, products, conditions for the following reaction of ammonium salts with heat (ammonium hydroxides)

you write the reactants, products, conditions for the following reaction of ammonium salts with exhaustive methylation
Compare acid-base properties of amines

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 amines with other basic organic compounds
Summarize the names and formulas for polycyclic and heterocyclic aromatic 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 the correct names/formulas for naphthalene

you write the correct names/formulas for anthracene

you write the correct names/formulas for phenanthrene

you write the correct names/formulas for pyridine

you write the correct names/formulas for pyrrole

you draw correct structure for naphthalene

you draw correct structure for anthracene

you draw correct structure for phenanthrene

you draw correct structure for pyridine

you draw correct structure for pyrrole
Compare acid-base properties of heterocyclic aromatic 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 compare the acidity/basicity heterocyclic amines with other acidic and basic organic compounds
Explain the theory of UV and mass spectrometry

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, absorbance and molar absorptivity

you identify UV energy states

you explain IR active molecular vibrations

you explain how a mass spectrometer works

you relate magnetic states of nuclei to NMR
Interpret IR, NMR, UV and mass 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 parts in spectra.

you summarize energy transitions

you summarize compounds that absorb in UV-VIS

you summarize lambda max

you summarize functional groups present and absent

you summarize different proton environments and number of protons

you summarize different C environments

you summarize molecular ions

you summarize fragmentation patterns

you summarize isotopic patterns

you propose structures for compounds using information above
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