Organic Chemistry II
Organic Chemistry II CHM 2211C
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This 4 page Class Notes was uploaded by Bridie Lynch on Thursday October 29, 2015. The Class Notes belongs to CHM 2211C at Valencia College taught by Staff in Fall. Since its upload, it has received 74 views. For similar materials see /class/231196/chm-2211c-valencia-college in Chemistry at Valencia College.
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Date Created: 10/29/15
Reactions Carbonyl Condensation Chapter 23 Part 1 Condensation Reactions Carbunyi compounds are both tno Eiectrupniie ano nooioooniio in carbunyi oonoonsation rEaEtiDn Electrophilin mimoyx moi Nuclcophilir mum n ma Iy nuclnnnhilcs Muck electmphilcl Condensation Reactions 2 carbonyl compounds I These carbonyl compoundsi ude aldeh s ketones esters amides acid anhydrides thiol esters and nitriles ncl I A combination of an titsubstitution reaction and a nucleophilic addition reaction between 231 Mechanism of Carbonyl Condensation Reactions Base Catalyzed Carbunyi oonoonsation rEaEtiDnS utiiiZE wsubstitutiun steps An enuiate ion aoos as a nooioooniio to ma oiootiooniiio acceptor 232 Condensations of Aldehydes and Ketones The Aldol Reaction Acetaidenyde reacts in basis suiutiun NaOEt NaOH Witn anotnoi rnuiecuie or acetaidnyde Tno Brnydruxy aidenyde product is aidealdehyde aicunoJ ii i ii 203011 outcnicnicn Tnis is a generai rEaEtiDn utaidehydes ano ketunes Acetnldchyde Aldo at s t u 14in imy aldehyde Aldol Mechanism Aldol Reactions I The aldehyde or ketone must have an C hydrogen I Condensation products are favored for monosubstituted d carbons Reactants are favored for disubstituted d carbons I Some aldol reactions with aldehydes o CH3CHZCH2ampH Na H39 20 Butanal Some aldol reactions With ketones I Aldol condensations are not favorable for tones o CH35CH3 NaOH H20 Acetone 7 Problem Write the structure of the aldol condensation product l Pentan al I 3Methylbutan al I 2Methylbutan al I Cyclopentanone Dehydration of Aldol Products Synthesis of Enones I hydroxy aldehydes can yield 15 unsaturated aldehydes conjugated enones Base catalyzed Pentanal NaOH H O 80 C Mechanism Dehydration I Dehydration can help drive aldol reactions of etones forward Cycluhexanaune cyciunayimenemciunexanu ne Problem What enune piuuucr would you expect from the aldol condensation of the following compounds l Cyclopentanone l Acetophenone l 3Methylbutanal Recognizing Aldol Products Starting materials Products Problem Which of the following are aldol condensation products What is the aldehyde or ketone precursor of each I 223Trimethyl3hydroxybutanal l b 2Methyl2 hydroxypentanal l c 5EthyI4methyl4hepten3one Mixed aldol reactions can lead to a single product if I one of the carbonyl components contains no crhydrogens and can t form an enolate ion can t be a donor l Formaldehyde or benzaldehyde l R NaOl l H20 CH30 CH CH3CCH3 Acetone prlvlethoxybenzaldehyde a Note CH30QCH CHCCH3 H20 dehydration is 39nvolved ArprMethoxyphenylVSVbuterrVZVone Mixed Aldon Condensations I Considerthe reaction of acetaldehyde and propanal and a base Problem Give the product of the mixed aldol condensation reaction product of benzaldehyde with Problem Which of the following could be prepared by a mixed aldol condensation reaction O CHCH20H3 Aldol Condensations and Synthetic Organic Chemistry 3 on SW 3 CHSCHQCHQCH 439 CHECHZCHZCHcHCH QCH Butanai ZrEthyiVSVhydroxyhexanai HQ Ni OH I CHSCHQCHQCHQHCHQOH CHQCHS ZrEthyH Senexanedioi Intramolecular Aldol Reactions I Common with14 or 15 diketones I The mechanism is similarto other aldol reactions with a Senone as a product NaOH CH3CHZOH H20 o o CHSECHZCHZcCH3 25Hexanedione CH3 Practice NaOH 26heptanedione H30H20H NaOH CH30H2OH Last Slide Chapter 23 part 1