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by: Brady Spinka


Brady Spinka
GPA 3.98

John Colapret

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John Colapret
Class Notes
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This 8 page Class Notes was uploaded by Brady Spinka on Monday September 7, 2015. The Class Notes belongs to CH 310N at University of Texas at Austin taught by John Colapret in Fall. Since its upload, it has received 17 views. For similar materials see /class/181877/ch-310n-university-of-texas-at-austin in Chemistry at University of Texas at Austin.




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Date Created: 09/07/15
ORGANIC LECFURE smug CH 310 N LECTURE 6 Textbook Assignment Chapter 16 Aldehydes amp Ketones Homework for credit Problem set 1 due today Today s Topics Carbonyl Compounds Addition Rxns 391mm 8c gIIIIDIIII BmBIItEI ORGANIC LECTURE SERIE Aldehydes And Ketones Overall Synthetic Transformation of Wittig Reagents amp Its Variations R R39 C ALKENES OR OLEFINS jk A v U KETONE CAN BE CYCLIC ORGANIC LECTURE SERIE Wittig Reaction The Wittig reaction is a very versatile synthetic method for the synthesis of alkenes olefins from aldehydes and ketones 00 Ph3PCH2 gt ltgtCH2 Ph3PO Cycloh exanone A pho sphonium ylide Methylene TIiphenyl cyclohexane pho sp hine oxide Ylides are reagents or reactive intermediates which have adjacent charges 63 G PthQHZ H Ph3P CH2 Wittig Reaction mums Phosphonium ylides react with the CO group of an aldehyde or ketone to give an alkene Step 1 nucleophilic addition of the ylide to the electrophilic carbonyl carbon 5 R2 39C39ZCR DD 2 39 gt 1 I gt i Ph3 Ph3 PCHZ Ph3 A betaine An oxaphosphetane Step 2 decomposition of the oxaphosphatane Ph3P CH2 gt Ph3 R2c CH2 Triphenylphosphine An alkene oxide ORGANIC LECTURE SERIE Wittig Reaction gtO ph3W gt W ph3po Acetone 2 Methyl 2 he pten e a PhYO Ph3P gt Ph Ph Ph3P0 H Z1Ph my 12 E 1 Phen yl 2 Phenyl butene butene acetaldehyde 87 13 Resonance stabilized Wittig reagent H 0 o Phko Ph3P lOEt gtPhJ0Et ph3p0 Phenyl Ethyl E 4 phenyl 2 butenoate acetald ehyde only the E isomer is formed Wittig Reaction mums some Wittig reactions are Z selective others are E selective Wittig reagents with an anionstabilizing group such as a carbonyl group adjacent to the negative charge are generally E selective 398 I I Ph P ltgt 3 3 CE Ph3POEt Resonance contributing structures for an ylide stabilized by an adjacent calbonyl group Wittig reagents without an anionstabilizing group are generally Z selective ORGANIC LECTURE SERIE Resonance Stabilization 0 o R02P C RO2P e lc 05 c OEt H65 IL R O R02Prz2c05t H Use of Stabilized Wittig Reagent C LECFURE 131115 1 treatment of a phosphonoester with a strong base followed by an aldehyde or ketone gives an alkene 2 a particular value of using a phosphonoesterstabilized anion is that they are almost exclusively E selective l I NleO2PCH2C0Et I Ogt N03 MeoIfO39 O OMe Only the Eisomer Dimethylphosphate is formed anion ORGANIC LECTURE SERIE lAddition Reactions to Carbonyl Compoundsl L w KETONE CAN BE CYCLIC H 0 Nu HNu U ALCOHOLS OR THEIR DERIVATIVES Note Water can be added to ketones amp aldehydes GANIC LECFURE smug Addition of H20 to Carbonyl Addition of water hydration to the carbonyl group of an aldehyde or ketone gives a geminal diol commonly referred to a gem diol gemdiols are also referred to as hydrates acid or co i quotquot39cOH H20 OH Carbonyl group A hydrate of an aldehyde a gemdiol orketone 39l39l RGAMCLECTURESERIE Addition of H20 to Carbonyl when formaldehyde 9 is dissolved in water at 20 C the carbonyl group is more than 99 hydrated H HgtO H20 gtltOH H H OH Formaldehyde Formaldehyde hydrate gt99 the equilibrium concentration of a hydrated ketone is considerably smaller OH 0 L gt H20 gtltOH ACNOOIIe 22Pmpanedi01 999 o 0109 12 GANIC LECFURE smug Addition of Alcohols to Carbonmyls Addition of one molecule of alcohol to the 00 group of an aldehyde or ketone gives a hemiacetal Hemiacetal a molecule containing an OH and an OR or OAr bonded to the same carbon acid or OH gto HOR in gtltOR A hemiacetal ORGANIC LECTURE SERIE Formation of a hemiacetal base catalyzed Step 1 proton transfer from HOR gives an alkoxide reversible A 39 3ng 2 9H oR Na OCH3 Step 2 attack of RO on the carbonyl carbon C9 95 CH3CCH3 TOR CH3CCH3 no Step 3 proton transfer from the alcohol to 039 gives the hemiacetal and generates a new base catalyst 6 6H 39I I CH3cCH3 H QR CH3CIICH3 19R OR 19R WORKSHEET Mechanism Provide a mechanism for the following transformation Show all important flows of electrons charges and intermediates 0 EtOH HO OEt gt Cka H30 aq catalytic DD Show the protonation step Show the attack of ethanol step this step must account for the regeneration of the catalyst H 0 3 Show the protonated hemiacetal Show the final product


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