CEM242 Course Objectives

Unit V – Radical Chemistry, Synthesis, Alcohols, and Phenols

5.1          The student will be able to draw resonance structures of radical compounds.

5.2          The student will be able to determine the weakest C-H bond in a compound.

5.3          The student will be able to differentiate the six common radical patterns and draw fishhook mechanisms for each

5.4          The student will be able to draw a mechanism for Radical Halogenation

5.5          The student will be able to predict the selectivity and stereochemical outcome of Radical Bromination

5.6          The student will be able to predict the products of Allylic Bromination.

5.7          The student will be able to predict the products of Radical Addition of HBr.

5.8          The student will be able to design a synthesis to change the identity or position of a functional group.

5.9          The student will be able to design a synthesis to change the carbon skeleton of a compound.

5.10        The student will be able to describe the process of retrosynthetic analysis.

5.11        The student will be able to name alcohols as per IUPAC standards.

5.12        The student will be able to identify oxidation/reduction reactions in organic reactions.

5.13        The student will be able to draw the mechanism and predict the outcome of Hydride Reductions.

5.14        The student will be able to describe how to prepare specific alcohols via a Grignard Reaction.

5.15        The student will be able to propose reagents capable of converting an alcohol to an alkyl halide.

5.16        The student will be able to predict the outcome of an oxidation reaction on an alcohol.

5.17        The students will be able to integrate alcohol reactions into overall organic synthesis reactions.

Unit VI – Ethers, Epoxides, and Spectroscopy

6.1          The student will be able to name ethers and epoxides as per IUPAC standards.

6.2          The student will be able to describe the production of an ether through the Williamson Ether Synthesis.

6.3          The student will be able to describe the preparation of an epoxide.

6.4          The student will be able to draw the mechanism and predict the outcome of the reaction between a strong nucleophile and an epoxide.

6.5          The student will be able to draw the mechanism and predict the outcome of an acid-catalyzed ring-opening.

6.6          The student will be able to extend concepts of hydroxyl groups to thiol groups in terms of mechanism.

6.7          The student will be able to describe the addition of two adjacent functional groups through an epoxide intermediate.

6.8          The student will be able to determine the appropriate Grignard Reaction for a given outcome.

6.9          The student will be able to determine the basic structural components of an IR spectrum.

6.10        The student will be able to distinguish between two compounds in an IR spectrum.

6.11        The student will be able to use the relative abundance of the (M=1)+· Peak to propose a Molecular Formula.

6.12        The student will be able to calculate HDI (Hydrogen Deficiency Index).

6.13        The student will be able to describe the theoretical basis of IR and Mass Spectroscopy.

6.14        The student will be able to describe the theoretical basis for NMR Spectroscopy.

6.15        The student will be able to distinguish the generally accepted facets of an NMR Spectrum.

6.16        The student will be able to infer structural insights from an NMR spectrum.

6.17        The student will be able to differentiate between the purpose of 1H and 13C spectrums.

Unit VII – Conjugated Pi Systems, Pericyclic Reactions, Aromatics Compounds and Substitution

7.1          The student will be able to differentiate between different organic systems containing multiple pi-bond systems.

7.2          The student will be able to make a cursory argument based on Molecular Orbital Theory to explain Electrophilic systems.

7.3          The student will be able to propose a mechanism and predict the products of an Electrophilic Addition to a Conjugated Diene.

7.4          The student will be able to predict the products of a Diels-Alder Reaction

7.5          The student will be able to predict the product of an Electrocyclic Reaction

7.6          The student will be able to use the Woodward-Fieser Rules to Estimate λMAX (wavelength of maximum absorption)

7.7          The student will be able to name polysubstituted benzene compounds by IUPAC rules.

7.8          The student will be able to determine whether a structure is aromatic, nonaromatic, or anti-aromatic.

7.9          The student will be able to determine whether a lone pair is part of aromaticity.

7.10        The student will be able to explain the meaning of aromaticity.

7.11        The student will be able to integrate aromatic side chains into synthesis schemes.

7.12        The student will be able to predict the products of a Birch Reduction.

7.13        The student will be able to determine the effects of a substituent on the aromatic ring.

7.14        The student will be able to use direction effects and blocking groups to accomplish synthesis of polysubstituted benzene rings.

Unit VIII – Aldehydes, Ketones, Acids, Enols and Enolates

8.1          The student will be able to identify and name Ketones, Aldehydes, Carboxylic Acids, Enols, and Enolates as per IUPAC rules.

8.2          The student will be able to describe the synthesis of an aldehyde and ketone.

8.3          The student will be able to describe the mechanism for the production of acetal, hemiacetal, imine, enamine, and thioacetal.

8.4          The student will be able to predict the major products of a Wittig or HWE Reaction.

8.5          The student will be able to describe the synthesis of carboxylic acids and their derivatives.

8.6          The student will be able to use pKa to describe the nature of the acid.

8.7          The student will be able to describe the use and purpose of the Gilman Reagent.

8.8          The student will be able to describe the spectroscopy of carboxylic acids and their derivatives.

8.9          The student will be able to draw enolates from given carbonyls.

8.10        The student will be able to predict the products of an aldol reaction.

8.11        The students will be able to predict the products of an aldol condensation.

8.12        The students will understand the Malonic Ester, Acetoacetic Ester, Stork Enamine, Claisen Condensation syntheses and when to use them.