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CH 220 Learning Objectives Exam 2 Chapter 4 Understand and be able to explain electrophilic addition reactions involving alkenes Epoxidation Oxidation reactions in acid as well as base o Hydroxylation o Oxidative cleavage Resonance structures and stability of allylic carbocations Drawing and interpreting resonance forms Be able to identify conjugated and isolated alkenes Understand the reaction of addition of HX or X2 to a conjugated diene o Identify 1 2 and 1 4 products Understand and be able to explain the following reactions involving alkynes o Addition of HX Hydrohalogenation o Halogenation o Addition of water Hydration o Hydrogenation When using regular metal catalyst When using Lindlar catalyst o Formation of acetylide ion Sections from the book 4 6 4 11 Chapter 5 Recognize aromatic compounds and be able to name them using current IUPAC nomenclature as well as ortho meta para nomenclature Recognize common names of aromatic compounds and be able to use them in combination with IUPAC or ortho meta para nomenclature Be able to determine the product of the following electrophilic aromatic substitution EAS reactions as well as the active electrophile in these reactions o Bromination Chlorination o Nitration o Sulfonation o Friedel Crafts Alkylation o Friedel Crafts Acylation Be able to determine the product of the following reactions o Oxidation of alkyl benzenes using potassium permanganate o Reduction of alkyl alkenyl benzenes using a reducing agent Recognize the groups that will act as ortho para activators meta deactivators and ortho para deactivators in electrophilic aromatic substitution reactions Be able to rank relative reactivity of substituted benzenes towards EAS Be able to determine the products of previously mentioned electrophilic aromatic substitution reactions when directing groups are present on a benzene ring Be able to identify structures that are heterocycles Be able to identify a suitable route in a short multistep synthesis of an organic target Sections from the book 5 1 5 10 Chapter 6 Recognize when a tetrahedral carbon is a chirality center Be able to count chirality centers present in a molecule Recognize whether a molecule is chiral or achiral Be able to apply the Cahn Ingold Prelog sequence rules to rank and determine the configuration of a chirality center Be able to name a molecule using IUPAC rules including the configuration of chirality centers Be able to draw a molecule with a specific configuration Identify whether a pair of isomers are enantiomers diastereomers the same molecule or constitutional isomers Sections from the book 6 1 6 10 Chapter 7 Understand and be able to explain in detail the mechanism of bimolecular nucleophilic substitution Be able to recognize alkyl halides haloalkanes and name them using current IUPAC nomenclature Identify how to prepare a Grignard reagent Be able to recognize a substrate starting material nucleophile and leaving group SN2 unimolecular nucleophilic substitution SN1 unimolecular elimination E1 and bimolecular elimination E2 Understand the relative rates of reactivity of substrates and alkyl halides in the reactions listed above Given a substrate solvent leaving group and nucleophile be able to predict the major organic product s of a reaction and its correct stereochemistry Given a set of conditions predict the outcome of a reaction in which elimination and substitution mechanisms are in competition Understand the following reactions o Reaction of alcohols with hydrogen halides o Reaction of alcohols with thionyl chloride and pyridine o Reaction of alcohols with phosphorus tribromide or trichloride and pyridine o Formation of Grignard reagents o General substitution reactions SN1 SN2 o General elimination reactions E1 E2 Sections from the book 7 1 7 10

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