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