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18-2 - 18—11 Synthesis of Aldehydes and Ketones from Acid...

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Unformatted text preview: 18—11 Synthesis of Aldehydes and Ketones from. Acid Chlorid'es 827 fa ”i acylation (Section 17-11) F O G ' ll ' A1C13 --R—C—-C1 + ——> . C~R (+ ortho) v” sky! or and; and ketone _; hydrogen, an activating group, or halogen. I _, n - Koch formylation (Section 17—! l C) G 0 AlClR CuCl ll HCl + C0 + -——‘—"’ G C’H benzaldehyde derivative 1 hydmgen an activating group, or halogen. , #alkynes (Section 9- 9F) ' ‘1: I by acid and mercuric Salts (Markomikov orientation) 0 Hg”, 112304 R\ /H ll R—CEC—H ?____—a C=C ——" R‘C—CHg 320 / \ alkyne HO H methyl ketone enol (not isolated) __J 1.: r rationr oxidation (anti—Ma rkovnikov orientarion) , R H 0 fl (1) 512121314 \ fl / ll R~C=C—-H —————’—’(2) H202, NaOH / ——C\ ——> R CHZ—C H alkyne H OH aldehyde enol (not isolated) 7' r'; ofIJ—dithianes (Section 18—8) A (1) BuLi m (1) BuLi m ° ; (2) 1° R' ——X S s s (”1 R‘X s s s >< alkylation >< alkylation >< H H R H R R' 1,3-dithiane thioacetal thioketal Lino: HoCl, ingot ngm2 O O i l / \ / \ r R H R R' aldehyde ketone I18 0 . H 0+ n (1) BuL1 (l) BuLi 3 /C\ S S S X (2) PhCHZBr S (2) BnBr chl Bu CHZPh H H H CHzPh Bu CHth thioacctal thioketal l-phenylvlhexanone (Continued) 1,3-dithiane ...
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