Organic Chemistry II
Organic Chemistry II CHEM 212
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This 0 page Study Guide was uploaded by Herta Weber on Sunday November 1, 2015. The Study Guide belongs to CHEM 212 at Pennsylvania State University taught by Staff in Fall. Since its upload, it has received 203 views. For similar materials see /class/233168/chem-212-pennsylvania-state-university in Chemistry at Pennsylvania State University.
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Date Created: 11/01/15
CHEM 212 Exam 2 Study Guide Chapter 18 Sections 1811815 Be able to draw the general mechanism for electrophilic aromatic substitution and be able to draw resonance structures for the carbocation intermediate Know the ve basic EAS reactions understand what the electrophile is for each and be able to draw the products of each Understand what is meant by electrondonating and electronwithdrawing groups and be able to tell the difference Understand inductive and resonance effects and be able to predict each for a given substituent Understand what groups are activating and deactivating and know why Know if groups are op directors or m directors and why Be able to draw the products of EAS reactions of monosubstituted benzenes Know the rules and be able to predict the products for EAS reactions of disubstituted benzenes Be able to draw the products for the side chain reactions discussed in class Bromination and subsequent elimination Benzylic oxidation Reduction of aryl ketones Reduction of nitro groups Be able to propose retrosynthetic analyses and short syntheses for polysubsituted benzenes Chapter 19 191194 1971911 Know the basic structure and nomenclature of carboxylic acids Know and understand the basic physical and spectroscopic properties of carboxylic acids Understand the acidbase reactions of carboxylic acids Be able to draw the resonance structures of a carboxylate ion and explain why carboxylic acids are more acidic than alcohols Understand and be able to explain how inductive effects affect the acidity of aliphatic carboxylic acids Understand and be able to explain how the presence of EDG and EWG affect the acidity of substituted benzoic acids Chapter 20 201204 2072014 Know the basic structure of all the carbonyl containing functional groups aldehydes ketones carboxylic acids acid chloride esters and amides Understand and be able to draw the mechanism for the two general reactions that carbonyl compounds undergo nucleophilic addition and nucleophilic acyl substitution Understand why aldehydes undergo nucleophilic additions and not nucleophilic substitutions Understand the relationship of leaving group ability to reactivity in nucleophilic acyl substitution reactions Understand the basics of oxidation and reduction in carbonyl compounds Know the structure of the two common reducing agents used to reduce ketones and aldehydes sodium borohydride and lithium aluminum hydride Know the mechanism for the reduction of aldehydes and ketones by these reagents Be able to draw the products for the reduction of aldehydes and ketones with LAH NaBH4 and catalytic hydrogenation Be able to draw the products for the reduction of acid chlorides and esters to aldehydes with lithium tritertbutoxyaluminum hydride and DIBAH respectively Be able to draw the products for the reduction of acids and amides with LAH Know the structure and how to make the three basic types of organometallic regents Understand how organometallic reagents can act as bases as well as nucleophiles Be able to draw the products for the reaction of aldehydes and ketones with organometallic reagents Be able to do the retrosynthetic analysis for alcohols to determine all the ways they can be synthesized from organometallic reagents and carbonyl compounds Be able to draw the products for the reaction of G1ignard reagents and organolithiums with esters and acid chlorides Be able to draw the products for the reaction of acid chlorides with organocuprates Be able to draw the products for the reaction of organometallics with epoxides and carbon dioxide Be able to draw the product for the reactions of organometallics with a5unsaturated carbonyl compounds 12 and 14 addition If covered in class before the exam CHEM 212 Exam 3 Study Guide Chapter 20 Be able to draw the product for the reactions of organometallics with or5unsaturated carbonyl compounds 12 and 14 addition Chapter 2 1 Understand the basic structure reactivity properties and nomenclature of aldehdyes and ketones Be able to draw the basic mechanism for nucleophilic addition and acidcatalyzed 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 ketonesaldehydes 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 acidcatalyzed 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 DIB AH and LAH Reaction with organometallics Chapter 23 Be able to draw the enols forms of different carbonyl compounds Know the general mechanism of the orsubstitution of enols Be able to give the products for the acid catalyzed orhalogenation reaction Know general features of enolate ions how and why they form resonance structures thermodynamic vs kinetic enolates EXplain the acidity of orhydrogens 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 orsubstitution 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 CHEM 212 Exam 1 Study Guide Chapter 14 Sections 1411411 Understand the basic theory of nuclear magnetic resonance NMR spectroscopy Be able to determine the number of equivalent protons in a compound Be able to differentiate equivalent nonequivalent enantiotopic and diastereotopic hydrogens Understand what shielding and deshielding is and the effects on chemical shift Know the general chemical shifts for protons in certain environments ie alkyl aromatic adjacent to a heteroatom etc Understand how to interpret the integration of a proton spectrum Understand how to interpret simple and complex spinspin splitting Understand the basics of carbon NMR Be able to determine the number of equivalent carbons in a molecule Know the general chemical shifts for carbons in certain environments ie alkyl aromatic adjacent to a heteroatom etc Be able to propose a structure if given a proton and or carbon NMR spectrum as well as other pertinent physical data such as IR and molecular formula Chapter 16 Sections 1611615 Understand the basic idea of conjugation Understand the basic concept of resonance and be able to draw resonance structure for common systems such as allyl conjugated double bonds cations adjacent to lone pairs polarized bonds Understand what a resonance hybrid is Know the basic stereochemical nomenclature for conjugated dienes Know the four distinguishing features of the CC bond in conjugated dienes Understand the nature of the stability of l3conjugated dienes Be able to write the mechanism and products of electrophilic addition to conjugated dienes Understand the difference between the kinetic and thermodynamic products in electrophilic addition Be able to explain which is which and why they are formed in differing amounts under different conditions Be able to write the mechanism and products for the DielsAlder reaction Understand the basic rules of dienedienophile reactivity and stereochemistry in the DielsAlder Understand the difference between endo and exo products in the DielsAlder reaction Understand the basic nature of how conjugated dienes absorb UV light Chapter 17 Sections 17 ll78 Dependent on what is covered in class through Friday Jan 30 Understand the basic structure and properties of benzene Know the basic nomenclature for simple substituted benzenes Understand the basic nature of benzenes stability and reactivity Know the criteria for aromaticity be able to determine if compounds are aromatic anti aromatic or not aromatic nonaromatic Understand the basic structure of aromatic heterocycles Understand the basic structure of charged aromatic compounds Sections covered and Suggested Problems Chapter 14 Sections 1411411 Problems 319 22 23 2536 3842 4451 5558 6063 Chapter 16 Sections 1611615 Problems 110 1224 2833 3552 56 57 59 Chapter 17 Sections 171178 Problems 119 2530 33234 36 3842 4650 54
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