CHEM 140B Chapter Notes - Chapter 20: Acyl Halide, Grignard Reaction, Lego Mindstorms
19 Mar 2017
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Ochem textbook notes chapter 20: carboxylic acid derivatives. 20. 1 relative reactivities, structures, and spectra of carboxylic acid derivatives. 20. 2 chemistry of acyl halides they undergo addition-elimination reactions in which nucleophiles displace the halide: catalyst usually not necessary. Numerous reactions that acyl halides can undergo. 1) water hydrolyzes acyl chlorides to carboxylic acids. 2) alcohols convert acyl chlorides into esters: base added to neutralize hcl by-product. 3) amines convert acyl chlorides into amides: tertiary amines cannot form amides since no hydrogens are available to be lost. 4) organometallic reagents convert acyl chlorides into ketones: use of diorganocuprates: more selective than rli or rmgx. 5) selective reduction of acyl chlorides results in aldehydes. Esters hydrolyze to carboxylic acids; the leaving-group problem: strong bases promote ester hydrolysis, mechanism: Grignard reagents transform esters into alcohols: use 2 equivalents of grignard reagent, mechanism: Esters are reduced by hydride reagents to give alcohols or aldehydes. Esters form enolates that can be alkylated.
