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Chapter 5 acyl chloride
This document covers topics related to organic chemistry II, including: - The general formula and nomenclature of carboxylic acids. - The preparation of acid chlorides from carboxylic acids and their reactivity. Acid chlorides are more reactive than acids due to the chlorine withdrawing electron density. - Common reactions of acid chlorides including reduction, Friedel-Crafts acylation, and nucleophilic acyl substitution such as hydrolysis, ammonolysis, and alcoholysis.
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Chapter 5 acyl chloride
- 1. CHM 301: OrganicChemistry II
- 2. General formula: RCOCl, Nomenclaturecarboxylic acids from Preparation acid chloride: Reactions of 1. Reduction 2. Friedel-Crafts Acylation 3. Nucleophilic Acyl Substitution Reactions •Hydrolysis, •Ammonolysis, •Alcoholysis •RCOOH, RCOO Na - + Prepared by Zildawarni Irwan 2
- 3. • Represent as: O R C Cl Or RCOCl •More reactive than acids; halogen, Cl withdraws e- density from carbonyl makes C carbonyl a very good electrophile. Prepared by Zildawarni Irwan 3
- 4. Named byreplacing -ic acid with -yl chloride. O C Br Cl O CH3CHCH2C Br Cl 3-bromobutanoyl chloride Benzoyl chloride Prepared by Zildawarni Irwan 4
- 5. Draw the structuralformulae 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 Irwan 5
- 6.
- 7. Show how thefollowing compounds can be prepared a)C6H5COCl from C6H5COOH b)CH3COCl from CH3CN Prepared by Zildawarni Irwan 7
- 8. 1. Reduction 2. Friedel-CraftsAcylation 3. Nucleophilic Acyl Substitution Reactions •Hydrolysis, •Ammonolysis, •Alcoholysis •RCOOH (carboxylic acid) •RCOO Na (carboxylate) - + Prepared by Zildawarni Irwan 8
- 9. 1° alcohol Reduction Reduction Aldehyde Aromatic ketone FriedelCraft Acylation Prepared by Zildawarni Irwan 9
- 10. Prepared by ZildawarniIrwan 10
- 11. Propose a mechanismfor the following reaction. Show all electron flow with curved arrows and draw all intermediate structure(s). Prepared by Zildawarni Irwan 11
- 12. Hydrolysis acid Alcoholysis ester NH3 Ammonolysis NH2 Ammonolysis amide N-substitute amide acid anhydride RCOO-Na+ Preparedby Zildawarni Irwan NaCl acid anhydride 12
- 13. Prepared by ZildawarniIrwan 13
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