CHEM 2724: Organic Chemistry II

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Subject:
Chemistry
Credit hours: 4 Lecture hours: 3 Lab hours: 4
PCS code (Local ID):
Baccalaureate/Transfer
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Course Description

The student will use reaction mechanisms and intermediates to determine products of organic reactions. The student will be able to use basic spectroscopy data to determine the structure of organic compounds. AAS: Physical science (laboratory science) elective.

Prerequisite(s)

CHEM 2714 with a grade of C or better

IAI Number
CHM 914
IAI Title
Organic Chemistry II
Course Fee
$40
Topical Outline
  1. Infrared Spectroscopy: absorption spectroscopy, electromagnetic spectrum, c=λν, E=hv, photons, infrared region, wavenumbers, molecular vibrations, infrared spectrum, bond stretching frequencies, finger
    print region, IR active and inactive vibrations, infrared spectrometer, FT-IR, reading and interpreting IR spectra (C-C bond stretching, conjugation, C-H bond stretching, characteristics of alcohols, amines, carbonyl compounds, C-N bonds, etc)
  2. Mass Spectrometry: the mass spectrometer, electron impact ionization, fragmentation, molecular ion, separation of ions by mass, the mass spectrum, base peak, GC-MS, HRMS, fragmentation patterns in MS, reading and interpreting mass spectra Interpreting IR and MS together
  3. Nuclear Magnetic Resonance Spectroscopy: NMR theory, nuclear spin, magnetic field, NMR absorption, shielding, NMR spectrometer, chemical shift, TMS, proton NMR chemical shifts, number of signals, chemically equivalent protons, area of peaks, measuring integral traces, splitting, N+1 rule, multiplet leaning, coupling constants, reading and interpreting Proton NMR spectra, C-13 NMR spectroscopy, carbon chemical shifts, comparison between proton and C-13, splitting, off-resonance decoupling, interpreting C-13 NMR spectra, using IR, MS, HNMR and C-13 NMR to deduce structure of an unknown compound
  4. Ethers, Epoxides and Thioethers: Ethers: structure, physical properties, as solvents, as complexes, IUPAC nomenclature, common names, cyclic ethers, Williamson ether synthesis, synthesis of phenyl ethers, alkoxymercuration-demercuration, bimolecular condensation of alcohols, cleavage of ethers by HBr and HI, autooxidation of ethers Thioethers: properties, naming, synthesis via Willamson, generation of thiolate ions, oxidations, as nucleophiles Silyl ethers: as alcohol protecting groups Epoxides: synthesis, peroxyacid epoxidation, cyclization of halohydrins, acid and base catalyzed ring opening of epoxides, reactions with Grignards and organolithiums
  5. Conjugated Systems, Orbital Symmetry and Ultraviolet Spectroscopy: conjugation, stability of dienes, Molecular orbitals of conjugated systems, allylic cations, 1,2-and 1,4-additions, kinetic and thermodynamic control in additions, allylic radicals, molecular orbitals of allylic systems, allylic anions, SN2 reactions of allylic halides and tosylates, Diels-Alder reaction mechanism, Ultraviolet absorption spectroscopy, absorptions and electronic transitions, Beer’s law, interpreting UV-Vis spectra
  6. Aromatic Compounds: structure, properties, stability, MOs, energy diagrams of benzene, Aromatic, Antiaromatic and Nonaromatic compound/ion criteria, Huckel’s Rule, IUPAC Nomenclature of benzene derivatives, physical properties
  7. Reactions of Aromatic Compounds: electrophilic aromatic substitution reaction/mechanism, halogenation, nitration, sulfonation of benzene and substituted benzene, activating and deactivating groups, ortho-, para-, meta- directing substituents, effect of multiple substituents on EAS, Friedel-Crafts alkylation and acylation reaction Clemmensen reduction, nucleophilic aromatic substitution mechanisms (addition-elimination and elimination-addition), substitutions using organometallics, Heck reaction, Suzuki reaction, addition reactions of benzene derivatives, catalytic hydrogenation of aromatic rings, Birch reduction, oxidation of phenols, EAS of phenols
  8. Ketones and Aldehydes: carbonyl structure, IUPAC nomenclature of ketones and aldehydes, common names, physical properties of ketones and aldehydes, industrial importance, synthesis of ketones and aldehydes (review: oxidation of alcohols, ozonolysis of alkenes, Friedel-Crafts acylation, hydration of alkynes), synthesis of ketones from carboxylic acids/organolithiums, ketones and aldehydes from nitriles/organometallics, reduction of nitriles using Al hydrides, aldehydes and ketones from acid chlorides and esters, reactions of ketones and aldehydes: nucleophilic addition to carbonyl groups mechanism, hydration, formation of cyanohydrins, imines, condensations with amines, formation of acetals, acetals as protecting groups, Wittig reaction, oxidation of aldehydes, reductions of ketones and aldehydes
  9. Amines: Primary, secondary, tertiary amines, quaternary ammonium salts, IUPAC nomenclature and common names, structure, physical properties, basicity and factors affecting, basicity, electrophilic aromatic substitution of arylamines/pyridine, nucleophilic aromatic substitution of pyridine, alkylation and acylation of amines, formation of sulfonamides, Hofmann Elimination, oxidation of amines, the Cope elimination, diazotination, synthesis, reductive amination, acylation-reduction, alkylation, reductions
  10. Carboxylic Acids: carboxyl group, carboxylate ion, nomenclature, common and IUPAC, dicarboxylic acids, structure and physical properties, acidity, factors that affecting, salts of carboxylic acids, commercial sources, synthesis, oxidations from alcohols and aldehydes, from alkenes, oxidation of alkylbenzenes, carboxylation of Grignard reagents, hydrolysis of nitriles, reactions of carboxylic acids and derivatives, nucleophilic acyl substitution, condensations, Fischer Esterification, using diazomethane, acids with amines, reduction of carboxylic acids, alkylation of carboxylic acids, synthesis and use of acid chlorides
  11. Carboxylic Acid Derivatives: Structure and IUPAC nomenclature of esters, amides, nitriles, acid halides, acid anhydrides, and multifunctional groups, physical properties, addition-elimination of nucleophilic acyl substitution, reactivity, interconversions, acid chloride to anhydride, ester, amide, acid anhydride to ester, amide, ester to amide, transesterification, hydrolysis of acid halides, anhydrides, esters (saponification), amides, nitriles, reduction of acid derivatives to alcohols, aldehydes, amines, reactions with organometallics
  12. Condensations and Alpha Substitutions of Carbonyl Compounds: alpha substitution, condensations, addition of enolate to aldehydes and ketones, substitution of an enolate on an ester, keto-enol tautomerism, alkylation of enolate ions, formation and alkylation of enamines, alpha halogenation of ketones, alpha bromination of carboxylic acids, acid and base catalyzed aldol condensation, dehydration of an aldol, crossed condensations, aldol cyclizations, Claisen ester condensation, syntheses, using β-dicarbonyl compounds, Malonic ester synthesis, acetoacetic ester synthesis

At the end of this course, students will be able to:

  • Employ appropriate and safe laboratory techniques to perform experiments, collaborating with partners.
  • Interpret the results of instruments to analyze reactions and products.
  • Employ laboratory skills and content knowledge to determine the identity of unknown compounds.
  • Report the results of laboratory experiments in a laboratory notebook, performing quantitative calculations and interpreting results.
  • Demonstrate an understanding of ultraviolet/visible spectroscopy, infrared spectroscopy, nuclear magnetic resonance spectroscopy (proton and carbon-13) and mass spectrometry by explaining the theory of these techniques and using spectra to determine the structure of an unknown organic molecule.
  • Draw structures for and provide IUPAC names for ethers, epoxides, aromatics, ketones, aldehydes, amines, carboxylic acids/derivatives, and discuss their structures, stability when appropriate, and predict physical properties such as melting point, boiling point and solubility. Provide common names when appropriate.
  • Provide detailed reaction mechanisms for the synthesis of ethers and epoxides and predict the products and provide mechanisms for the reactions of ethers and epoxides.
  • Discuss the structure and stability of conjugated unsaturated systems. Predict the products and provide detailed reactions mechanisms for addition reactions of conjugated systems and also the Diels-Alder reaction.
  • Determine whether Huckel’s rule applies to a given structure and predict whether the compound will be aromatic, antiaromatic, or nonaromatic.
  • Predict the products and provide detailed reactions mechanisms for electrophilic aromatic substitution reactions. Explain how substituent activating, deactivating and directing abilities influence major product formation.
  • Predict the products and provide detailed reactions mechanisms for nucleophilic aromatic substitution reactions.
  • Provide detailed reaction mechanisms for the synthesis of ketones and aldehydes. Predict the products and provide detailed reactions mechanisms for the reactions of ketones and aldehydes including nucleophilic additions.
  • Provide detailed reaction mechanisms for the synthesis of amines and predict the products and provide mechanisms for the reaction of amines.
  • Provide detailed reaction mechanisms for the synthesis of carboxylic acids. Predict the products and provide detailed reactions mechanisms for the reactions of carboxylic acids, including Fisher esterification.
  • Provide detailed reaction mechanisms for the synthesis of and predict products of reactions of various acid derivatives.
  • Predict the products and provide detailed reactions mechanisms for Aldol and Claisen condensations.