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CHM 234| Study guide 4

by: Alvin Notetaker

CHM 234| Study guide 4 CHM 234

Marketplace > Arizona State University > Chemistry > CHM 234 > CHM 234 Study guide 4
Alvin Notetaker
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General Organic Chemistry II
Study Guide
Organic Chemistry
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This 9 page Study Guide was uploaded by Alvin Notetaker on Wednesday April 27, 2016. The Study Guide belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 30 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.

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Date Created: 04/27/16
CHM 234 Study Guide 3    Aldehydes and Ketones​ :  Reaction of Acid Chloride  Nomenclature and ICPAC  Reaction Between Acid Chloride and  Preparing aldehyde/ketone  Organometallic Reagent  Relative reactivity for aldehyde and ketone  Oxygen Nucleophile​ :  Acid Anhydrides​ :  Hydrate Formation  Preparation and Reactions  Acetal Formation  Acetylation with Acetic Anhydride  Ester​:  Cyclic Acetal and reverse  Preparation via S​2  Stable Hemiacetal  N​ Nitrogen Nucleophile: ​  Preparation via  Fischer Esterification  Primary amine  Preparation via Acid Chloride  Secondary amine  Reaction of Ester  Wolf­Kishner Reduction  Acid­catalyzed Hydrolysis  Hydrolysis of Acetals, Imines, Enamines  Aminolysis of Ester  Sulfur Nucleophile​:  Reduction of Ester  Convert to alkane  Grignard Reaction with Ester  Hydrogen (Hydride) Nucleophile​ :  Amide​ :  Reagent  Hydrolysis of Amides (acid and base)  Reduction of Amides  Carbon Nucleophile​ :  Grignard Reaction  Nitriles  Cyanohydrin Formation  Preparation via SN​  Witting Reaction  Preparation via Amides  Baeyer­Villiger Oxidation of Aldehyde and  Hydrolysis of Nitriles (acid and base)  Grignard reaction of Nitriles  Ketone  Priority for placement/migrant of the oxygen atom  Reduction of Nitriles  Carboxylic acid​:  Alpha Carbon Chemistry: Enols and  Nomenclature  Enolates:​  Common name  α­carbon  Naming the carboxylic salts  α­hydrogen  Preparing Carboxylic acid  Increase in stability when α­hydrogen is  Carboxylation of Grignard Reagent  removed  Reaction of Carboxylic Acid  Enolates  Carboxylic acid derivatives:​  Forming Enolates  Nomenclature  Alpha Halogenation of Enol and Enolates  Reactivity of Carboxylic Acid Derivatives and  The Hell­Volhard­Zelinski Reaction  why?  Base­Promoted halogenation  Nucleophilic Acyl Substitution  Halogenation of Methyl Ketone  Acid Halide​:  ­­­­(Haloform reaction)  Preparation and Reaction of Acid Chloride  Aldol Reaction and reverse  Hydrolysis of Acid Chloride  Alcoholysis of Acid Chloride  Aminolysis of Acid Chloride  Answers:  Aldehydes and Ketones​ :  Nomenclature and ICPAC:  ● Aldehyde: “­al”  ● Ketone” ­one”  Preparing aldehyde/ketone:  ● Oxidation of secondary alcohol  ○ PCC with CH2Cl2  ○ Na2Cr2O7 with H2SO4  ● Ozonolysis of alkenes  ○ 1) O3 with 2) DMS  ● Acid­catalyzed hydration of terminal alkynes  ○ H2SO4, H2O with HgSO4  ○ goes to more substituted  ○ enol to keto  ● Hydroboration­oxidation of terminal alkynes  ○ 1) R2BH with 2) H2O2, NaOH  ○ goes to less substituted  ● Friedel­Crafts Acylation  ○ ketone with a halide with Al(halide)3  Relative reactivity: (most to least)  1. Formaldehyde  2. Aldehyde  3. Ketone  Oxygen Nucleophile​ :  Hydrate Formation  ● Steric effect  ● Electronic effect  Acetal Formation  ● Reagent:  ○ 2 ROH with [H+] (ketone to two ester group)  Cyclic Acetal and reverse  ● Reagent:  ○ ketone with (CH2)2(OH)2 (forms a cyclic compound)  ● Act as a protection  Stable Hemiacetal  ● Reagent:  ○ H+  (forms a cyclic compound)  ● One compound that has a ketone and an alcohol group  ● The partial negative oxygen in the alcohol group bonds itself with the carbon of the  ketone  Nitrogen Nucleophile: ​  Primary amine  ● For double bond C­N  ● Reagent:  ○ Trace acid  ○ [H+]  ○ TsOH  Secondary amine  ● Forms double bond C­C  Wolf­Kishner Reduction  ● Reduction from carbonyl to alkane  ● Reagent:  ○ N2H2 and then KOH/H2O  Acetals  ● Forms carbonyl and alcohol group  Imines  ● Forms carbonyl and amine  Enamine  ● Forms carbonyl and amide  Sulfur Nucleophile​ :  Convert ketone to alkane  ● Reagent: (after protecting)  ○ H2 with Raney Ni  Hydrogen (Hydride) Nucleophile​ :  Hydrogen (Hydride) Nucleophile  ● Reagent  ○ 1. LAH with 2. H2O  ○ NaBH with MeOH  Carbon Nucleophile​ :  Grignard Reaction  ● Reagent:  ○ RMgBr with H2O  Cyanohydrin Formation  ● Reagent:  ○ HCN with KCN (Ketone to nitrile)  ○ 1. LAH with 2. H2O (Nitrile to amine)  ○ H+ (Nitrile to carboxylic acid)  Witting Reaction  ● Reagent:  ○ carbonyl with phosphonium (P(C6H5)3)  ● A S​ 2 prefer less hindered molecule.  N​ (Note: Just look at the phosphonium. It prefers the less hindered segment.)  Baeyer­Villiger Oxidation of Aldehyde and Ketone  ● Reagent:  ○ Peroxyacid  Priority for placement/migrant of the oxygen atom:  ● H>3°>2°Phenyl>1°>methyl  Carboxylic acid​ :  Nomenclature and ICPAC for Carboxylic acid  ● Remove “­e” with “­oic acid”  Common name  ● Position is labeled with Greek letter starting at the carbon of the acid.  Naming the carboxylic salts  ● First name the cation  ● Name the anion by replacing “­ic acid” with “­ate”  Preparing Carboxylic acid  ● Oxidation Cleavage of Alkynes  ○ 1. O3 with 2. H2O  ● Oxidation of Primary Alcohol  ○ Na2Cr2O7 with H2SO4, H2O  ● Oxidation of Alkylbenzenes  ○ Na2Cr2O7 with H2SO4, H2O  ● Hydrolysis of Nitriles  ○ H+ with heat  Carboxylation of Grignard Reagent  Reagent:  ● 1. CO2 with 2. H3O+  Reaction of Carboxylic Acid  Reagent:  ● 1. LAH with H3O+  ● BH3THF  Carboxylic acid derivatives    X  Name  Cl  Acid halide  COOR  Acid anhydride  OR  Ester  NH​ Amide  2  Nitrile, RCN, is a acid derivative    Carboxylic acid derivatives​ :  Nomenclature for Carboxylic acid derivatives  Naming Acid Halide  Replace “­ic acid” with “­yl halide”  Naming Acid Anhydride  Replace “acid” with “anhydride”  Naming Easter  Replace “­ic acid” or “oic acid” with “­ate”  Naming Amide  Replace “­ic acid” or “­oic acid” with “amide”  If the amide group have a alkyl group substituents, their names are place with a “N” as the  locant.  Naming Nitrile  Replace “­ic acid” with “­oniltrile”    Reactivity of Carboxylic Acid Derivatives  Most to least  1. Acid halide  2. Acid anhydride  3. Ester  4. Amide  Nucleophilic Acyl Substitution  ● Acid ­ starts with proton transfer  ● Base ­ Start with nucleophilic attack  Acid Halide: ​  Preparation and Reaction of Acid Chloride  ● Reaction with carboxylic acid  ● Reagent:  ○ SOCl2  Hydrolysis of Acid Chloride  ● Acid chloride to carboxylic acid  Alcoholysis of Acid Chloride  ● Reagent:  ○ ROH and pyridine  Aminolysis of Acid Chloride  ● Reagent:  ○ (2 eq.) NH3  ○ (2 eq.) RNH2  ○ (2 eq.) R2NH    Reaction of Acid Chloride  ● Reagent:  ○ 1. ex. LAH with 2. H2O  ­  To stop of aldehyde:  ● Reagent:  ○ 1. LiAl(OR)3H and 2. H2O  Reaction Between Acid Chloride and Organometallic Reagent  ● Reagent:  ○ 1. ex. RMgBr with 2. H3O+  Acid Anhydrides​ :  Preparation and Reactions  ● Acetic anhydride is the only anhydride that can be form at high temperature.  ● All reactions are the same as acid chloride  Acetylation with Acetic Anhydride  ● Reagent:  ○ ROH  ■ Form ester  ○ RNH2  ■ Forms amide    Ester​:  Via S​2  N​ ● Reagent:  ○ 1. NaOH with 2. CH3I  (carboxylic acid to ester)  Via  Fischer Esterification  ● Reagent:  ○ CH3OH with H3O+ (carboxylic acid to ester with the R group on the alcohol)  Via Acid Chloride  ● Reagent:  ○ ROH with pyridine (Acid chloride to easter)  Reaction of Ester  ● Saponification  ● Reagent:  ○ NaOH with H3O+ ( ester to carboxylic acid)  Acid­catalyzed Hydrolysis  ● Reagent   ○ H3O+  (ester to carboxylic acid)  Aminolysis of Ester  ● Reagent:  ○ NH3 (ester to amide and alcohol)  Reduction of Ester  ● Reagent:  ○ 1. LAH with 2. H2O (form hydroxyl group)  ○ 1. DIBAH with 2. H2O (form aldehyde)  Grignard Reaction with Ester  ● Reagent:  ○ 1. ex. RMgBr with 2. H3O+ (ester to alochol and two Rs group)  Amide​ :  Hydrolysis of Amides (base and acid)  ● Reagent   ○ H3O+  (amide to carboxylic acid)  ○ NaOH, H2O with H3O+  (amide to carboxylic acid)  Reduction of Amides  ● Reagent:  ○ 1. ex. LAH with 2. H2O (amide to amine)  Nitriles​  Preparation via S2  N​ ● Reagent:  ○ 1. NaCN (alkyl halide to nitrile)  Preparation via Amides  ● Reagent:  ○ 1. SOCl2 ( amide to nitrile)  Hydrolysis of Nitriles  ● Reagent   ○ H3O+  (Nitrile to carboxylic acid)  ○ NaOH, H2O with H3O+  (Nitrile to carboxylic acid)  Grignard reaction of Nitriles  ● Reagent:  ○ 1. ex. RMgBr with 2. H3O+ (Nitrile to ketone)  Reduction of Nitriles  ● Reagent:  ○ 1. ex. LAH with 2. H2O (Nitrile to amine)  Alpha Carbon Chemistry: Enols and Enolates​ :  α­carbon  ● Carbon adjacent to a carbonyl carbon.  α­hydrogen  ● Hydrogen bonded to α­carbon  Increase in stability when α­hydrogen is removed  1. Creates a delocalized electron  2. Delocalized electrons moves to the more electronegative atom, oxygen.  Enolates  ● Is the resonance­stabilisation when deprotonation of the alpha position.  Forming Enolates  ● Reagent:  ○ LDA  ○ NaH  Alpha Halogenation of Enol and Enolates  ● Reagent:  ○ Br2 with H3O+  ● Forms one halogen on the α­carbon  ● Reaction with ketone  The Hell­Volhard­Zelinski Reaction  ● Reagent:  ○ 1. PBr3, Br2 with 2. H2O  ● Forms one halogen on the α­carbon  ● Reaction with carboxylic acid  Base­Promoted halogenation  ● Reagent:  ○ Br2 with ­OH  ● Forms two halogen on the α­carbon  Halogenation of Methyl Ketone (Haloform reaction)  ● Reagent:  ○ (ex.) I2 with ­OH  ● Can be with any halogen.  Aldol Reaction and reverse  ● Two of the same compound react with base (­OH) and water to make a carbon­carbon  bond on the α­carbon. 


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