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Orgo 2 Lecture 13-14

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by: MelLem

Orgo 2 Lecture 13-14 CHEM 225

Marketplace > Simmons College > Chemistry > CHEM 225 > Orgo 2 Lecture 13 14
Simmons College
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13-14 carboxylic acid derivatives cont. and lipid introduction
Organic chemistry 2
Professor gurney
Class Notes
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This 4 page Class Notes was uploaded by MelLem on Tuesday April 5, 2016. The Class Notes belongs to CHEM 225 at Simmons College taught by Professor gurney in Spring 2016. Since its upload, it has received 20 views. For similar materials see Organic chemistry 2 in Chemistry at Simmons College.

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Date Created: 04/05/16
Orgo 225 Lecture 13 21.12 Preparation and Reactions of Amides Preparation of amides  Amides can be prepared from any of the carboxylic acid derivatives  Most efficiently prepared from acid chlorides Reactions Acid Catalyzed Hydrolysis of Amides Amides can be hydrolyzed to give carboxylic acids Base catalyzed Hydrolysis of Amides Amides can also be hydrolyzed when heated in basic aqueous conditions (this process is very slow) Reduction of Amides When treated with LAH, amides are converted to amides  The carbonyl group is completely removed 21.13 Preparation and Reactions of Nitriles Preparation of nitriles via SN2 reaction Nitriles can be prepared by treating an alkyl halide with a cyanide ion Preparation of nitriles from amides  Nitriles can be prepared via dehydration of an amide Hydrolysis of nitriles Occurs in aqueous acid conditions Nitriles are hydrolyzed to amides then further hydrolyzed to carboxylic acids Reactions between nitriles and Grignard reagents A ketone is obtained when a nitrile is treated with a Grignard reagent Grignard attacks the nitrile – the resulting anion is treated with aqueous acid to give an imine then hydrolyzed to a ketone Reduction of nitriles Nitriles are reduced to amines when treated with LAH 21.14 Synthesis Strategies C-C bond forming reactions c-c bond forming reactions in which the F.G remains the same: 1) Xs RMgBr 2) H2O R2CuLi 1) RMgBr 2) H3O+ In class lecture 13 summary: o Nucleophiles (Nu) – frequently negative, but sometimes not. o Pyridine is not a nucleophile because it wont attack an electrophilic carbon due to sterics since N is in the Ring.  New Rxn: o Hydrolysis of amides  Saponification – hydrolysis of amides in basic conditions  1) NaOH 2) H3O+  Under Acidic Conditions –  H3O+ o Reduction of Amide  LAH  Knocks out the carbonyl group. o Nitriles SN2 rxn  NaCN o Dehydration  SOCl2  Gives you the product + H2O o Reduction with LAH  From oxidation level 3  1 because LAH is a strong reducer  Reduces nitriles down to amines Carboxylic acids are the only acid derivative that don’t get attacked at the carbonyl.  Anytime you start with a carboxylic acids, react with SOCl2 to make an acid chloride  It will never be wrong to go to an acid chloride then down to a lower reactivity. LIPIDS 26.1 Introduction to Lipids and Lipid Chemistry Lipids – defined by the physical property, solubility. Complex lipids – lipids that are readily able to undergo hydrolysis in aqueous acid Lipids are either: Complex Lipids (can be hydrolyzed) o Waxes o Phospholipids o Triglycerides Simple Lipids (cannot be hydrolyzed) o Steroids o Prostaglandins o Terpenes All three of the complex lipids contain ester moieties – rendering them easily hydrolyzed. They also contain long hydro carbon chains – making them soluble in organic solvents. 26.3 Triglycerides o Triglycerides are triesters formed from glycerol and 3 long chain carboxylic acids (commonly known as fatty acids) o A triglyceride is said to contain 3 fatty acid residues o (They are used by mammals and plants for longer term energy storage) Lecture 14 In Class summary Lipids – be able to distinguish between saturated and unsaturated fats, soaps, steroids, waxes, phospholipids, recognize fat vs H2O soluble vitamins. Be able to draw a typical triglyceride Know how to make a soap, and how soap works. Know triacyl glycerides Hydrolysis under basic and acidic conditions: Under basic conditions = saponification Know how to draw amino acids with the side chain given, be able to classify them as nonpolar, polar neutral, polar basic, or polar acidic. PI – isoelectric point  when the zwitter ion exists (neutral overall – but has charges)  Be able to draw an amino acid in varying pH’s  At a lower pH, the N has a + charge and is NH3  Neutral but still charged – N has a + charge, CO- charge  At pH higher than the PI (NH2) and CO has a – charge


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