CHEM 2202 Organic Chemistry II

CHEM 2202 Organic Chemistry II

CHEM 2202 – Organic Chemistry II

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I.COURSE TITLE: Organic Chemistry II

COURSE NUMBER: 2202 CATALOG PREFIX: CHEM

II.PREREQUISITE(S): CHEM 2201

COREQUISITE: CHEM 2212

III.CREDIT HOURS:4 LECTURE HOURS: 4

LABORATORY HOURS: 0OBSERVATION HOURS: 0

IV.COURSE DESCRIPTION:

This course is designed to give the student extensive background in bonding, nomenclature, and reactions of organometallics, alcohols, diols, ethers, epoxides, aldehydes and ketones. Reactions of these types of compounds or leading to their formation will be covered, including electrophilic aromatic substitutions and nucleophilic additions to the carbonyl group to enolates and organometallics. Spectroscopy of organic compounds will be introduced.

A course designed to give the student extensive background in bonding, nomenclature, and reactions of carboxylic acids and their derivatives, amines, aryl halides and phenols. Reactions of these types of compounds or leading to their formation will be covered. Basis biomolecules such as carbohydrates, lipids, amino acids, and proteins and nucleic acids will be introduced with an emphasis on their basic primary, secondary and tertiary structures, as appropriate, and certain simple properties and reactions from an organic chemical perspective.

V.ADOPTED TEXT(S):

Organic Chemistry

10th Edition

Carey and Giuliano, 2016

McGraw-Hill

ISBN: 978-0-07-351121-4

VI.COURSE OBJECTIVES:

At the end of the course, the student should be able to:

  1. Describe the difference in bonding and structure between organometallic compounds and other compounds of the same metals.
  1. Predict the product of nucleophilic addition to the carbonyl group by enolate anions and organometallics and understand the mechanism involved.
  1. Determine IUPAC names of arenes, aldehydes, ketones, ethers and organometallics.
  1. Understand nucleophilic acyl substitution.
  1. Understand the chemistry and acidity of carboxylic acids and their derivatives.
  1. Understand the chemistry of amines and phenols.
  1. Understand the chemistry of ester enolates.
  1. Understand the chemistry of polymers, both industrial and biological.
  1. Understand the rudiments of biological chemistry including carbohydrates, lipids, proteins, nucleosides, nucleotides, nucleic acids and others.

VII.COURSE METHODOLOGY:

Lecture room with computer with PowerPoint and projector, internet connection for the computer and projector to access review and discussion materials on the McGraw-Hill web site that accompanies the text. Molecular models foe hands-on demonstration of the structure of organic chemicals. Student-accessible computer equipment adequate to run the molecular modeling CD-ROM that accompanies the text.

VIII.GRADING

A / 90 / – / 100
B / 80 / – / 89
C / 70 / – / 79
D / 60 / – / 69
F / 0 / – / 59

IX.COURSE OUTLINE:

  1. Organometallic compounds.
  1. Introduction focused on organolithium and organomagnesium compounds.
  1. Preparation using alkyl halide compounds including the free-radical mechanism of formation and the choice of solvent for stability.
  1. Reactions discussed include reduction of alkyl halides and the preparation of alcohols from aldehydes and ketones.
  1. Discussion of organometallic compounds as catalyst for optically active drug preparation.
  1. Alcohols, diols and thiols.
  1. Nomenclature, physical properties and sources are discussed.
  1. Preparation including hydration of alkenes, Grignard reagents with aldehydes and ketones, hydrogen reduction of aldehydes and ketones, and lab scale reduction of aldehydes and ketones.
  1. Preparation of diols by reduction of compounds containing two carbonyl groups and vicinal diols via osmate esters.
  1. Reactions of alcohols including Fisher esterification and oxidation products such as aldehydes, ketones and carboxylic acids.
  1. Ethers, epoxides and sulfides.
  1. Nomenclature and physical properties are discussed including Crown ethers.
  1. Safety considerations when working with ethers is emphasized.
  1. Preparation and reactions of epoxides is discussed.
  1. Aldehydes and ketones
  1. Nomenclature, structure and physical properties are discussed.
  1. Reactions including formation of geminal diols, cyanohydrins and hemiacetals are included.
  1. Imines and enamines are discussed.
  1. Enols and enolates.
  1. Definition of enols and enolates and how they work is given.
  1. Aldol condensation and alkylation of enolate ions is discussed.
  1. Keto-enol tautomerism is discussed.
  1. Alpha-halohydrogenation of aldehydes and ketones and the haloform reaction is shown.
  1. Carboxylic acids.
  1. Nomenclature, characterization and physical properties including acidity and pKa values is discussed.
  1. Preparation is given.
  1. Reactions are given including the formation of a tetrahedral intermediate during esterification.
  1. Derivatives of acids are given including nomenclature and reactivity.
  1. Ester enolates.
  1. The Claisen condensation is discussed including Dieckmann cyclization.
  1. Discussion of acetoacetic ester synthesis and malonic ester synthesis is given.
  1. Amines.
  1. Nomenclature and physical properties are discussed.
  1. Preparation of amines is given including the formation of Schiff bases.
  1. Reactions are discussed.
  1. Aryl halides
  1. Preparation is discussed.
  1. Reactions including nucleophilic substitutions and the formation of benzyne is discussed.
  1. Phenols.
  1. Nomenclature and physical properties including resonance considerations and pKa effects are given.
  1. Reactions including electrophilic aromatic substitution and attacks at the phenol oxygen is discussed.
  1. Selected biomolecules.
  1. Structures, properties, nomenclature and reactions of carbohydrates is given.
  1. Structures, properties, nomenclature and reactions of lipids and steroids is given.
  1. Structure of amino acids and their combination to form peptides and proteins is given.
  1. Nucleosides, nucleotides and nucleic acids are discussed.
  1. Polymers.
  1. Types of polymers are discussed.
  1. Both natural and man-made polymers are discussed.
  1. Properties such as thermoplasticity and glass transition temperature are discussed.

X.OTHER REQUIRED TEXTS, SOFTWARE, AND MATERIALS:

The molecular modeling CD-ROM bundled with the text is required and will be used with College supplied computer resources. Other books and materials will be supplied in the class.

XI.EVALUATION:

Student evaluation is by quizzes and examinations. Additional homework or a paper may be required or may be permitted for remedial work or extra credit.

XII.SPECIFIC MANAGEMENT REQUIREMENTS:

At the discretion of the instructor

XIII.OTHER INFORMATION:

FERPA: Students need to understand that your work may be seen by others. Others may see your work when being distributed, during group project work, or if it is chosen for demonstration purposes. Students also need to know that there is a strong possibility that your work may be submitted to other entities for the purpose of plagiarism checks.

DISABILITIES: Students with disabilities may contact the Disabilities Service Office, Central Campus, at 800-628-7722 or 937-393-3431.

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