Acid chlorides L.O. To be confident identifying an acid chloride To know how acid chlorides react

Acyl Chlorides NomenclatureNamed from the corresponding carboxylic acid remove -ic add -yl chloride CH 3 COCl ethanoyl chloride C 6 H 5 COCl benzene carbonyl (benzoyl) chloride Chemical properties: colourless liquids which fume in moist air attacked at the positive carbon centre by NUCLEOPHILES these include water, alcohols, ammonia and amines undergo addition-elimination reactions

Acyl chlorides ReagentWater Product(s)carboxylic acid + HCl (fume in moist air / strong acidic solution formed) Conditionsroom temperature EquationCH 3 COCl(l) + H 2 O(l) CH 3 COOH(aq) + HCl(g) Mechanismaddition- elimination Key point: You will see steamy fumes of HCl being given off. This is a good way of testing for an acyl chloride. Acyl chlorides DO NOT react with PCl 5, so this is also a good differentiation test. What does react with PCl 5 ?

Acyl chlorides ReagentAlcohols Product(s)ester + hydrogen chloride (you will get the characteristic ester smell and fumes of HCl (g)) Conditions room temperature and dry (anhydrous) conditions EquationCH 3 COCl(l) + CH 3 OH(l) CH 3 COOCH 3 (l) + HCl(g) Mechanismaddition- elimination Remember: Esters can also be made from ________ and ________ Making esters using carboxylic acids slower, reversible, low yield Making esters using acyl chlorides faster, better yield, must be dry

Acyl Chlorides ReagentAmmonia Product(s)amide + hydrogen chloride Conditions Low temperature and excess ammonia; vigorous reaction. EquationCH 3 COCl(l) + NH 3 (aq) CH 3 CONH 2 (s) + HCl(g) orCH 3 COCl(l) + 2NH 3 (aq) CH 3 CONH 2 (s) + NH 4 Cl(s) Mechanismaddition- elimination

Acyl Chlorides ReagentAmines (primary amine!) Product(s)N-substituted amide + hydrogen chloride Conditions room temperature and anhydrous EquationCH 3 COCl + C 2 H 5 NH 2 CH 3 CONHC 2 H 5 + HCl orCH 3 COCl + 2C 2 H 5 NH 2 CH 3 CONHC 2 H 5 + C 2 H 5 NH 3 Cl Mechanismaddition- elimination - similar to that with ammonia.

Questions 1.Describe tests that would allow you to distinguish between ethanoic acid and ethanoyl chloride. 2.Why do acyl chlorides react at room temperature? 3.What products are made when an acyl chloride reacts with ammonia? 4.Why must esterification using an acyl chloride be kept dry? 5.If a diacyl chloride reacted with a diamine what product could result?