5Aldehyde&Ketones - H + ket one unstable + al cohol...

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Aldehydes and Ketones C=O carbonyl group aldehyde ketone C and O are sp 2 hybridized 120 o
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Aldehydes and Ketones Nomenclature 1. Longest chain with C=O is parent 2. Suffix is “-al” or “-one” 3. C 1 is always C=O in aldehydes In ketones, C=O is given lowest number 4. C=O has precedence over -OH (called “hydroxy”)
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1 2 3 4 al butan 2-bromo-3-methyl one 1 2 3 4 5 pentan 3- cyclobutanone 1 2 3 2-methyl 3-hydroxy- trans -
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Physical properties δ - δ + polar higher b.p. than alkanes H-bond acceptor soluble in polar solvents no H-bond donor lower b.p. than alcohols O .. C H H .. O .. C H H .. : + -
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Reactions Reduction [ R ] = reducing agent LiAl H 4 NaB H 4 H 2 /Pt [ R ] [ R ] al one CH 3 - CH 3 - 1 2 3 4 butan CH 2 - CH 2 - C HO CH 2 - CH 2 - CH 2 - OH 1 2 3 4 butan 2-
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Review aldehyde ketone C = O very polar + δ + δ - δ + δ - H - Nu H - OH H - OR H - NH 2 H Nu O C H Nu O C : : O C : : Nucleophilic addition
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.. O H H .. Nucleophilic addition + + + H - OH H - OR H - NH 2 H + H + H + hydrate or diol + H + hemi - ketal C = O R R .. .. C = O R R .. .. C = O R R .. .. H + C O R R H C O- H R R O - H O .. H R .. C R R O- H O - R C O R R .. .. H N H H H .. C R R O - H N - H 2 + H + C R R N H + H 2 O Schiffs base
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+ CH 3 OH
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Unformatted text preview: H + ket one unstable + al cohol = ketal aldehyde unstable + alcohol = acetal C O H 3 C H 3 C C O CH 3 H 3 C hemi-H Addition of alcohol H hemi-H OCH 3 Nucleophilic acetal aldehyde + alcohol hemi -+ alcohol + H + H + .. .. acetal + H + condensation reaction hemi-acetal + alcohol acetal + H 2 O C H 3 C H OH O - CH 2- CH 3 OH - CH 3- CH 2 .. .. H C H 3 C H OH O - CH 2- CH 3 H 2 O O - CH 2- CH 3 H . C H 3 C H O - CH 2- CH 3 O - CH 2- CH 3 .. .. substitution acetal propanal + stable hemi-ketal 2-butanone + unstable 2 equivalents ethanol 1 equivalent methanol reverse reaction acetal + H 2 O H + hemi-acetal + alcohol Hydrolysis breaking water O O H OH ketal + H 2 O hemi-ketal + alcohol...
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5Aldehyde&Ketones - H + ket one unstable + al cohol...

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