Overview of Acyl Chlorides in Organic Chemistry

Acyl chlorides, also known as acid chlorides, are important compounds in organic chemistry. They can be prepared from carboxylic acids and thionyl chloride, and are reactive towards various nucleophiles leading to the formation of carboxylic acid esters, primary and secondary amides. Acyl chlorides can also react with water, alcohols, ammonia, and primary amines to form different derivatives such as carboxylic acids, esters, primary amides, and secondary amides. Understanding the reactivity and synthesis of acyl chlorides is crucial for organic synthesis.

• Acyl Chlorides
• Organic Chemistry
• Carboxylic Acids
• Amides
• Synthesis

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1. Acyl chlorides Acyl chlorides

2. The acyl group Carboxylic acid RCOOH Acyl group RCO Acyl chloride RCOCl O O O R C R C R C Cl OH Preparation of an acyl chloride From carboxylic acid and thionyl chloride, SOCl2 O O H3C C H3C C + SOCl2 + SO2 + HCl OH Cl Thionyl chloride Ethanoic acid Ethanoyl chloride

3. Acyl chlorides in synthesis Acyl chlorides in synthesis Acyl chlorides react with nucleophiles O O R C R C OH OR' carboxylic acid ester H2O R'OH O R C Cl acyl chloride NH3 R'NH2 O O R C R C NH2 NHR' secondary amide primary amide

4. Acyl chlorides Acyl chlorides Carboxylic acids and Esters Carboxylic acids and Esters Carboxylic acids using water O O + H2O H3C C + HCl H3C C Cl OH Water ethanoyl chloride ethanoic acid Esters using alcohols O O HCl + H2O + H3C C CH3CH2CH2 OH H3C C O CH2CH2CH3 Cl water hydrochloric acid ethanoyl chloride propan-1-ol Alcohol propyl ethanoate

5. Acyl chlorides Acyl chlorides Amides Amides Primary amides using ammonia O O H3C C + 2NH3 + NH4Cl H3C C NH2 Cl Ammonia ethanoyl chloride primary amide Secondary amides using primary amines O O + CH3NH3+ Cl H3C C H3C C + 2CH3NH2 Cl N H CH3 Primary amine ethanoyl chloride secondary amide