Unit 1 Section 2 Notes
Unit 1 Section 2 Notes CHEM 334 E03
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This 7 page Class Notes was uploaded by Natalie Lopez on Monday September 14, 2015. The Class Notes belongs to CHEM 334 E03 at University of South Carolina - Columbia taught by Dr. George Handy in Summer 2015. Since its upload, it has received 124 views. For similar materials see Essentials of Organic Chemistry II in Chemistry at University of South Carolina - Columbia.
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Date Created: 09/14/15
UNIT ONE SECTION TWO Reactions of Aldehydes and Ketones Addition of Carbon Nucleophiles o The Grignard Reagent R39MgX Discovered by Victor Grignard 1892 X is a halide o Iodides are the most expensive but the most efficient o Chlorides are least reactive but the cheapest o Bromides are the best in reactivity and expense R can be an alkyl or aryl group Ether is used to make the reagent 0 This forms a soluble complex stabilizing RMg X Diethyl ether cannot be used at high temperatures so THF is used as a solvent instead How to form the Grignard Reagent Free Radical Reaction Pathway Applying the Grignard Reagent Synthesis of alcohols 0 Using an aldehyde ketone or epoxide and reacting with the Grignard reagent will result in an alcohol o Aldehydes will yield a 2 alcohol o Ketones will yield a 3 alcohol o Epoxides will yield a 1 alcohol o Alkyne Nucleophiles HCEC39 I How it is made o H hydration o o Cyanide Nucleophiles 39CEN I How it is made I Applying Nucleophile o A cyano group can be hydrolyzed into a carboxy group via acid hydrolysis o o The result in the following reaction would be carboxy acid and NH4 o Organolithium Reagents 39CH3 Li I How it is made 0 CH3 Li bond is polar I Applications of Reagent o More reactive than Grignard Reagent 0 Used in synthesis of alcohols o The Wittig Reagent CHz PC5H53 I Aldehydes and ketones react with phosphorane to create alkenes and triphenylphosphine oxide 0 AKA 9 The Wittig Reaction I How it is made 0 Must be made in its original place starting with an alkyl halide with the same amount of carbons as the carbon on the phosphorus atom of Wittig Reagent I Application of the Wittig Reagent I 0 Addition of Nitrogen Nucleophiles 0 ALL reactions are reversible and acidcatalyzed o Mechanism I Forward process is shown by steps 4 5 and 6 in the diagram above I Reverse process is shown below K r l quotJ 4 2 Raf l 4 r v l 5 C I Examples of Addition of a Nirogen Nucleophile I Transamination 0 Biochemical process in which the body converts an amino acid available in large quality to an amino acid in short supply via an enzyme bound aldehyde 0 Mechanism 0 Oxygen Nucleophiles 0 Addition of Water to Aldehydes and Ketones I Formaldehyde and water is the most reactive I Acetone and water is the least reactive I Acetaldehyde and water have intermediate reactivity 0 Addition of oxygen nucleophiles to carbonyl compounds I Aldehydes or Ketones 0 With methanol I Application example 0 An acid catalyst is used in the first rxn H o In most cases reaction goes to completion to form acetalsketals
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