Unit 1 Section 1
Unit 1 Section 1 CHEM 334 E03
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This 6 page Class Notes was uploaded by Natalie Lopez on Saturday September 5, 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 230 views. For similar materials see Essentials of Organic Chemistry II in Chemistry at University of South Carolina - Columbia.
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Date Created: 09/05/15
729778 aldehyde and ketone UNIT ONE ALDEHYDES AND KETONES Introduction 0 Aldehydes contain a carbonyl group CO bonded to a carbon atom on one side and a hydrogen atom on the other 0 ll lC H o GeneralformulaRCHO o Ketones contain a carbonyl group CO bonded to a carbon atom on both sides 0 or ll C l l iref K 0 General formula RCOR Nomenclature of Aldehydes and Ketones o Aldehydes o Aldehyde must be at the end of the carbon chain I Do NOT need to indicate its position 0 Replace the final e with the suffix a PropanaI 0 When attached to a ring system I Add suffix carbaldehyde 39 0 o Ketones 0 Chain is numbered to give the carbonyl carbon the lowest number possible 0 Replace the final e with the suffix one I 2pentanone Physical Properties 0 The carbonyl group is polar The oxygen is more electronegative making the C0 bond polar o 7 757 Newng C o w r we v Q W quoti m H 6 14H39C ig 0 Causes aldehydes and ketones to have higher boiling points than hydrocarbons of same molecular weight 0 Due to lack of hydrogen bonding in aldehydes and ketones between their molecules they have a lower boiling point than of the equivalent alcohols o Aldehydes lt Ketones lt Alcohols lt Carboxylic Acid 0 Carbonyl group allows aldehydes and ketones to form hydrogen bonds with the water 0 Result in appreciable solubilities in water I Like dissolves like polar w polar nonpolar w nonpolar I 9 Synthesis of Aldehydes o Oxidation of Alcohols 0 Jones Reagent I Cr03 H2504 conc I Na2Cr207 H2504 conc I K2Cr207 H2504 conc o Pyridinium Chlorochromate Reagent I Cr03 HCl Pyridine CH2C2 I HCl is added to the solution rapidly and pyridine is added to neutralize the pH 0 0xidation state of aldehyde lies between a primary 1 alcohol and carboxylic acid 0 Aldehydes can be produced from 1 alcohols by using the PCC reagent I 7 Ex Ul f HYquot U 3 139 1 39 4quot f 39 2 ff W39 A 2 t cilto m o Oxidation of Glycols by periodic acid 0 Alkanes are cleaved or split 0 mm splits a glycol into two 0 o Hydration of AlkenesAlkynes o Markovnikov Addition I When treated with H2504 most commonly alkene will form alcohol I Reaction will proceed to give the more stable carbocation intermediate I Tautomeric shift will form ketone o AntiMarkovnikov I Instead of the H being added to the carbon with more H atoms it is added to the carbon with less H atoms 0 Reagents 39 H30 I Reducing 0 1 HgSO4 H2504 2 NaBH4 o OxymercurationMarkovnikov I Oxidizing 0 1 BH3 2 H202 OH o Hydroboration Anti o Ozonolysis of Alkenes o Alkenes can be cleaved at the double bond 0 Results in aldehydes and ketones 0 Can be done in two ways I Reductive Ozonolysis I Oxidative Ozonolysis c N 9L3 dko l H o Aldehydes by Reduction of Acyl Chlorides Esters and Nitriles 0 When any carboxylic acid reacts with LAH it is reduced all the way to a 1 alcohol past an aldehyde 0 The key is to use a carboxylic derivative I Acyl Chloride I Ester I Nitrile 0 And an aluminum hydride derivative I LiAlH OtBu I DIBAL H o Acyl Chlorides I Carboxylic Acids are reduced to Acyl Chlorides by using 5002 I Reduced to aldehydes by treating with LiAlH OtBu I O lt O 39 k I LHMH 0 t BILL 1 0 9 Cl 239 20 K H a H malachqu carboxylic OLUlcl GUM ohmhdo o Esters and Nitriles I Reduced to aldehydes by treating with DIBALH I Ester must be carried out at low temperatures 0 Diagram of synthesis of Acyl chlorides esters and nitriles Synthesis of Ketones o Ketones from Alkenes Arenes and 2 Alcohols o Alkenes can be cleaved giving ketones as a product I This uses Ozonolysis 0 2 alcohols undergo oxidation resulting in ketones I This uses PCC or Jones reagent 0 Ketones from Nitriles o A nitrile can be treated by the Grignard reagent or organolithium reagent followed by hydrolysis resulting in a ketone o The reagent takes place only ONCE If addition took place twice there would be a double negative charge on the nitrogen of the nitrile
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