chapter 5 acyl chloride

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  • 1. CHM 301: Organic Chemistry II

2. General formula: RCOCl, Nomenclature carboxylic acids from Preparation acid chloride: Reactions of 1. Reduction2. Friedel-Crafts Acylation 3. Nucleophilic Acyl Substitution ReactionsHydrolysis, Ammonolysis, Alcoholysis RCOOH, RCOO Na -+Prepared by Zildawarni Irwan2 3. Represent as: O RCClOrRCOCl More reactive than acids; halogen, Cl withdraws e- density from carbonyl makes C carbonyl a very good electrophile. Prepared by Zildawarni Irwan3 4. Named by replacing -ic acid with -yl chloride. O CBrClOCH3CHCH2C Br Cl3-bromobutanoyl chloride Benzoyl chloridePrepared by Zildawarni Irwan4 5. Draw the structural formulae for each of the following compounds: a) 3 - chloro - 4 - nitrobenzoyl chloride b) 4 - ethylbenzoyl chloride c) 4 - methylbenzoyl chloride Write the IUPAC names for the following compounds:Prepared by Zildawarni Irwan5 6. PCl3 33P(OH)3PCl5 POCl3Prepared by Zildawarni Irwan6 7. Show how the following compounds can be prepared a)C6H5COCl from C6H5COOH b)CH3COCl from CH3CNPrepared by Zildawarni Irwan7 8. 1. Reduction 2. Friedel-Crafts Acylation 3. Nucleophilic Acyl Substitution ReactionsHydrolysis, Ammonolysis, Alcoholysis RCOOH (carboxylic acid) RCOO Na (carboxylate) -+Prepared by Zildawarni Irwan8 9. 1 alcohol Reduction ReductionAldehydeAromatic ketone Friedel Craft AcylationPrepared by Zildawarni Irwan9 10. Prepared by Zildawarni Irwan10 11. Propose a mechanism for the following reaction. Show all electron flow with curved arrows and draw all intermediate structure(s).Prepared by Zildawarni Irwan11 12. HydrolysisacidAlcoholysisesterNH3AmmonolysisNH2AmmonolysisamideN-substitute amide acid anhydrideRCOO-Na+ Prepared by Zildawarni IrwanNaCl acid anhydride 12 13. Prepared by Zildawarni Irwan13

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