CHEM 140C Chapter 20: CHEM 40C Carboxylic Acid derivatives
15 Jan 2018
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H "s on carbon attached to carbonyl group have increased acidity due to resonance stabilization inenolate anion ( conjugate base ) more. tk#txghzt(ch,. ghztiorgthte~m resonance effects are stronger than inductive effects pka 16 pka 20 pka. C more most acidic inductive effects methyl electron donating resonance less acidic tsasicityof. Derivatives pka 30 effects least acidic protonation carbonyl at oxygen protonation at. Rk . fh+ nice , h no significant resonance bad because. + charge next to electron withdrawing carbonyl destabilizing inc charge. Acylhalibetwater ( acyl halide hydrolysis with water ) general form : pfkx + hzo. # nskc , to make acyl ( vysoclz ) Hokies only: acids is with reaction chlorides useless way bk. / r unwanted-04 g side rxn to avoid this used weak base amihelikettzn. H : base a if w/ eton - byproduct : nftp. 92amtnenronm. tl salt t. ie#a+y. anmiettatkyjksiamiaetdaika++y!y. ette7tiyfhnamiae. Acylhalidestliai ( or)3h aldehydes ( one stage reduction need to modify. Liaihy to prevent over reactivity w/ acyl halides.
