Organic Chemistry II - Exam 3 Study Guide | CHEM 212, Study notes of Organic Chemistry

Download Organic Chemistry II - Exam 3 Study Guide | CHEM 212 and more Study notes Organic Chemistry in PDF only on Docsity! CHEM 212 - Exam #3 - Study Guide Chapter 20 -Be able to draw the product for the reactions of organometallics with α,β-unsaturated carbonyl compounds: 1,2 and 1,4 addition. Chapter 21 -Understand the basic structure, reactivity, properties and nomenclature of aldehdyes and ketones. -Be able to draw the basic mechanism for nucleophilic addition and acid-catalyzed nucleophilic addition. -Know the basic structure of a phosphorous ylides and how they are formed. -Understand the mechanism of and be able to draw the products of the Wittig reaction -Be able to do the retrosynthetic analysis of alkenes to determine how they could be synthesized by reaction of a phosphorous ylides and carbonyl compounds. -Be able to draw the products for the reaction of amines with carbonyl compounds to form imines or enamines. -Be able to draw the products for formation of hydrates and acetals of ketones/aldehydes. -Understand how acetals can be used as protecting groups. Chapter 22 -Know the basic structure, nomenclature, properties and reactivity of carboxylic acids and their derivatives. -Understand the relationship between the basicity of the leaving group and a derivatives reactivity. -Know the basic mechanism of nucleophilic acyl substitution. -Be able to draw the products for the reactions of acid chlorides. - Reaction with carboxylates - Reaction with water - Reaction with alcohols - Reactions with amines -Be able to draw the products for the reaction of anhydrides -Reaction with water -Reaction with alcohols -Reaction with amines -Be able to draw the products for the reactions of carboxylic acids - Conversion to acid chlorides - Conversion to esters - Conversion to anhydrides - Conversion to amides -Know the mechanism and be able to draw the products of the base- and acid-catalyzed hydrolysis of esters. -Be able to draw the products for the hydrolysis of amides. -Understand the structure and reactivity of nitriles. -Be able to draw the products for the three common reactions of nitriles - Hydrolysis - Reduction with DIBAH and LAH - Reaction with organometallics Chapter 23 -Be able to draw the enols form(s) of different carbonyl compounds -Know the general mechanism of the α-substitution of enols -Be able to give the products for the acid catalyzed α-halogenation reaction -Know general features of enolate ions: how and why they form, resonance structures, thermodynamic vs. kinetic enolates -Explain the acidity of α-hydrogens, general trends in acidity for different carbonyl compounds and how different bases can be used to form the enolate and the effect on the equilibrium -Know the α-substitution reactions involving enolate ions: - Based catalyzed halogenation and the haloform reaction - Direct alkylation of aldehydes, ketones, esters and nitriles - Malonic ester synthesis, be able to give products and explain how it works - Acetoacetic ester synthesis, be able to give products and explain how it works