Review 3 - C haps 1 8 , 2 0 & 2 1 R e v ie w C h a p te r 1...

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Review
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Chapter 18. Topics • Ketones and Aldehydes: Structures and Properties • Methods of Preparation • Reactions -Nucleophilic Addition -Grignard Reactions -Condensation reactions • Application in Synthesis 2
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Preparation of Aldehydes and Ketones Previously discussed methods from alkenes by ozonolysis from alkynes by hydration (via enol) from arenes by Friedel-Crafts acylation from alcohols by oxidation 3
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• Treating carboxylic acids with organolitium (RLi) to give ketones Preparation of Aldehydes and Ketones C O O Li _ + CH 3 Li C O CH 3 O Li _ + Li + _ H 3 O + C OH CH 3 OH H 2 O _ C O CH 3 4
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• Treating nitriles with Grignard or organolithium reagents to give ketones H 3 O + CH 3 CH 2 MgBr + C N ether C CH 2 CH 3 N MgBr C CH 2 CH 3 O 5 Preparation of Aldehydes and Ketones
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• Reduction of acid chloride to aldehydes CH 3 CH 2 CH 2 C O H LiAlH(O- t -Bu) 3 CH 3 CH 2 CH 2 C O Cl • Reaction of acid chloride w/ R 2 CuLi to give ketones CH 3 CH 2 CH 2 Li 2 CuI (CH 3 CH 2 CH 2 ) 2 CuLi (CH 3 CH 2 CH 2 ) 2 CuLi + CH 3 CH 2 C O Cl CH 3 CH 2 C O CH 2 CH 2 CH 3 6 Preparation of Aldehydes and Ketones
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• Using 1,3-dithiane to give aldehydes and ketones S S S S •• H CH 3 CH 2 Br S S H CH 2 CH 3 HgCl 2 , H + H 2 O O H CH 2 CH 3 BuLi S S CH 2 CH 3 •• BuLi CH 3 Br S S CH 2 CH 3 H 3 C HgCl 2 , H + H 2 O O H 3 C CH 2 CH 3 7 Preparation of Aldehydes and Ketones
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• General mechanism: Reactions of of Aldehydes and Ketones: Nucleophilic Addition to C=O 8 Tetrahedral carbonyl addition compound + C R R O C Nu O - R R Nu -
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Carbonyl Reactivity C O H H R H O C R R' O C R OR O C > > > decreasing rate of reaction with nucleophile ! + ! " Basic Nucleophiles: RMgX, RLi, LiAlH 4 , NaBH 4 , RC = CNa Basic Nucleophile: - CN
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• Wittig reaction R R' O CHR'' R' R Ph 3 P-O - Ph 3 P-CHR'' Triphenyl- phosphine oxide Methylene- cyclohexane A phosphonium ylide + + - + + 10
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appropriate reagents, how would you synthesize 2- butene? 11
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This note was uploaded on 11/10/2010 for the course CHE 201 taught by Professor Bong during the Spring '08 term at SUNY Buffalo.

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Review 3 - C haps 1 8 , 2 0 & 2 1 R e v ie w C h a p te r 1...

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