CHEM& 262: Organic Chemistry II

Download as PDF

Class Program

Chemistry

Credits

Weekly Contact Hours

Course ID

091537

Meets Degree Requirements For

Natural Science with Lab

Description

The second of a three-quarter sequence in organic chemistry for university transfer, intended primarily for science majors and those fulfilling requirements for professional health science careers such as medicine, dentistry and pharmacy. CHEM& 262 furthers the development of the properties, transformations and identification of organic molecules. Lab included.

Grading Basis

Graded

Prerequisites

CHEM& 261

Course Learning Outcomes

Determine how the structure of organic compounds leads to physical and chemical properties and by utilizing these properties be able to predict reactions, devise synthetic strategies, separate mixtures, and deduce the identity of organic compounds.

Develop the ability to assess the common functional groups of organic chemistry for stability/reactivity in a variety of commonly encountered environments, including but not limited to acid/base, redox, and over a varied temperature range

Become proficient at the fundamental techniques of organic chemistry, both with respect to synthetic and separation techniques

Begin to see the interconversion of functional groups, to the point where seemingly disparate functionalities can be related to one another

Develop a working knowledge of the theoretical basis and practical application of analytical instrumentation routinely used in the organic chemistry based laboratory, and utilize data from these instruments to establish purity and determine the identity of samples of organic substances, both as unknown samples and to corroborate expected results from a synthetic procedure and product mixture purification

Research fundamental physical properties and reactivities for given organic molecules for use in synthesis, separation, and identification, with an emphasis on safety considerations and best practices for the minimization and disposal of waste Also, students will analyze peer reviewed journal articles for accuracy, clarity, context, and utility

Write a running laboratory journal and submit formalized lab reports. Successful students will also present synthetic strategies and rationale for structural assignment from a collection of analytical data before the entire class

Anticipate, recognize and respond to chemical hazards in the laboratory environment, and as encountered in day-to-day circumstances, based on reactivity (corrosiveness, electrophilicity, instability to standard conditions) as well as basic biochemical mechanisms (e.g. methylating agents)

Appreciate the organic chemistry principals underlying biochemical function (e.g. the human nucleophilic aqueous environment) and understand numerous biochemical processes in organic chemistry terms. Understand the disposition of specific drug and vitamin examples in organic chemistry terms

Develop an appreciation for and apply the principals of green chemistry in order to place organic chemistry within the greater context of application to solving the problems of mankind while minimizing impact on the environment

Function as a member of a team or group by working with a partner in the organic chemistry lab

Discuss synthetic strategies, devise separation protocols, develop assays, and interpret analytical data with fellow classmates

Core Topics

In Brief:

Radical reactions
Alcohols and ethers: properties and nomenclature of alcohols and ethers, synthesis and reactions of alcohols, synthesis and reactions of ethers
Organic redox reactions, organometallic compounds, Grignard reactions
Conjugated unsaturated systems: resonance, 1,4 addition, Diels-Alder reaction
Aromatic compounds: benzene, electrophilic aromatic substitution, Friedel-Crafts and related reactions
Aldehydes and ketones: additions to the carbonyl group
Analytical techniques: Nuclear magnetic resonance spectrometry, mass spectrometry, infrared and ultraviolet-visible spectroscopy further developed
HPLC and other chromatographic separation/sample purity techniques further developed

In Detail:

Interpret a 13C nmr spectrum in terms of carbon chemical shift and number of attached protons.
Identify compounds based on their 13C nmr spectra.
Identify compounds based on their two dimensional nmr spectra.
Explain the function of modern multi-dimensional and multi-sector mass spectrometers.
Define and utilize parent, daughter, and neutral loss spectra in identifying compounds in complex mixtures
Write detailed reaction mechanisms for a variety of free radical reactions, including radical polymerization reactions.
Explain anti-Markovnikov addition.
Name alcohols, ethers, organohalogen compounds, aromatic compounds, aldehydes, and ketones according to IUPAC rules.
Explain the physical properties of alcohols, ethers, aldehydes, ketones, and aromatic compounds.
Write equations for the synthesis of alcohols from alkenes using acid catalyzed hydration, oxymercuration/demercuration, and hydroboration/oxidation.
Write equations for reactions involving alcohols, including acid/base reactions, the formation and use of mesylates and tosylates, and their conversion into alkyl halides.
Write equations for the synthesis of ethers and the reactions of ethers.
Analyze the structure and reactivity of epoxides.
Explain the use of crown ethers as phase transfer catalysts.
Identify organic redox reactions.
Generate organometallic reagents, understand their key features and unique properties, and execute the synthesis of a variety of compounds from them.
Use resonance to explain the stability of allyl radicals and cations.
Know the rules of resonance and utilize them to explain the behavior of various  systems
Explain the bonding in conjugated unsaturated systems.
Write equations for 1,4-addition reactions of conjugated dienes.
Write equations for the synthesis of cyclic compounds using Diels-Alder reactions.
Use uv-vis spectra to aid in compound identification.
*******
Explain   *, n  * and related transitions
Explain the bonding in benzene and other aromatic compounds.
Describe the orbital basis for Hückels rule
Utilize Hückels rule to predict when compounds will be aromatic.
Write detailed reaction mechanisms for electrophilic aromatic substitution reactions.
Write equations for the synthesis of a variety of compounds using electrophilic aromatic substitution reactions.
Using a variety of reactions, write equations for the synthesis of aldehydes and ketones.
Write detailed reaction mechanisms for reactions involving addition to the carbonyl group.
Write equations for the synthesis of a variety of compounds using addition to carbonyl groups.
Practice standard laboratory safety precautions.
Skillfully communicate the results of laboratory work.
Design and carry out an experimental procedure to solve a specific problem.
Isolate and characterize natural products.
Synthesize organic compounds.
Obtain NMR, GC/MS, HPLC, FT-IR and other data to establish sample purity and compound identity
Use chemical reference material appropriately.
Work effectively in groups.