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CHM 234|Continuation of other nuleophiles and chapter 21

by: Alvin Notetaker

CHM 234|Continuation of other nuleophiles and chapter 21 CHM 234

Marketplace > Arizona State University > Chemistry > CHM 234 > CHM 234 Continuation of other nuleophiles and chapter 21
Alvin Notetaker
GPA 3.33

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Finishing chapter 20 Chapter 21: Carboxylic acid and their derivative
General Organic Chemistry II
Class Notes
Organic Chemistry
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This 11 page Class Notes was uploaded by Alvin Notetaker on Monday April 18, 2016. The Class Notes belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 12 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.

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Date Created: 04/18/16
Hydrolysis of Acetals, Imines, Enamines  Acetals    Mechanism:    Hydrolysis with a base is not effective meaning there will be no reaction occurring    Imines      Enamine      Sulfur Nucleophile  Act the same os oxygen.        Convert ketone to alkane.  Reagent:  H  with Raney Ni  2     Hydrogen (Hydride) Nucleophile    Mechanism:      Carbon Nucleophile  Grignard Reaction      Cyanohydrin Formation  Cyanohydrin ​ ­ the carbon with alcohol group and CN group.  Cyanide ion can act like a nucleophile.  Disadvantage​ : Extreme toxicity and volatility of hydrogen cyanide    Mechanism:      Advantage​ : Synthetic utility      Witting Reaction  Reagent:  ● carbonyl with phosphonium (P(C H ) )  6 5 3   This reaction forms alkene    Mechanism:      A S​N​ prefer less hindered molecule.  (Note: Just look at the phosphonium. It prefers the less hindered segment.)    Baeyer­Villiger Oxidation of Aldehyde and Ketone  Reagent:  ● Peroxyacid  Aldehyde forms Carboxylic acid  Ketone forms Ester  Mechanism:      Priority for placement/migrant of the oxygen atom:  H > 3° > 2° ≈ Phenyl > 1° > methyl    Chapter 21: Carboxylic acid and their derivative  Nomenclature of Carboxylic Acid  IUPAC Name  1. Remove “­e” with “­oic acid”  2. Carbon of the carboxylic acid is position 1  Common name  Position is labeled with Greek letter starting at the carbon of the acid.   Methanoic acid / Formic acid   3­bromopentanoic acid / β−bromovaleric acid    Naming the carboxylic salts  ● First name the cation   ● Name the anion by replacing “­ic acid” with “­ate”   potassium 3­chloropentanoate  ● With 2 carboxylic acids, put “­dioic acid”    Preparing Carboxylic acid  ● Oxidation Cleavage of Alkynes  ○ 1. O3 with 2. H 2   ● Oxidation of Primary Alcohol  ○ Na 2r O2 w7th H SO 2 H 4  2 ● Oxidation of Alkylbenzenes  ○ Na 2r O2 w7th H SO 2 H 4  2 ● Hydrolysis of Nitriles  ○  H  with heat    Carboxylation of Grignard Reagent  Reagent:  + ● 1. CO w2th 2. H O3      Reaction of Carboxylic Acid  Reagent:  ● 1. LAH with H O  + 3 ● BH ∙3HF     Mechanism:      Introduction to Carboxylic Acid Derivation  With no change to the oxidation state of the carbon is called, Carboxylic acid derivatives.    X  Name  Cl  Acid halide  COOR  Acid anhydride  OR  Ester  NH​ 2  Amide    Nitrile, RCN, is a acid derivative.    Naming Acid Halide  Replace “­ic acid” with “­yl halide”    Benzoyl chloride    Naming Acid Anhydride  Replace “acid” with “anhydride”    Acetic benzoic anhydride    Naming Easter  Replace “­ic acid” or “oic acid” with “­ate”    Ethyl acetate    Naming Amide  Replace “­ic acid” or “­oic acid” with “amide”    Acetamide    If the amide group have a alkyl group substituents, their names are place with a “N” as the  locant.    N,N­dimethylacetamide    Naming Nitrile  Replace “­ic acid” with “­oniltrile”    Benzonitrile    Reactivity of Carboxylic Acid Derivatives  Most to least  1. Acid halide  2. Acid anhydride  3. Ester  4. Amide    For an acid halide,   ● Inductive effect​  ­ The electronegative atom makes the carbon more electrophilic.   ● Resonance​  ­ Have three resonance where one of the three is not significant.(between  C­Cl)    For an amide,  ● Inductive effect​  ­ The nitrogen atom is a weak electronegative atom in comparison with  halide or oxygen.  ● Resonance​  ­ Have three resonance where all three are significant.(between C­N)    Nucleophilic Acyl Substitution  ● A two­step process    Mechanism:    ● This substitution must ​ not​ be written as a S​N​.    In acidic condition, avoid formation of a strong base.    Mechanism:      In basic condition, avoid formation of a strong acid.    So,  Acid ­ starts with proton transfer  Base ­ Start with nucleophilic attack    Preparation and Reaction of Acid Chloride  ● Reaction with carboxylic acid  ● Reagent:  ○ SOCl   2   Mechanism:      Hydrolysis of Acid Chloride    Mechanism:      Alcoholysis of Acid Chloride      Aminolysis of Acid Chloride     


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