Ch 13 Carboxylic Acids, Esters, Amines and Amides

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Ch 13 Carboxylic Acids, Esters, Amines and Amides SWBAT: Name/Draw compounds with functional groups Describe/Explain properties of functional groups Complete/Show reactions of functional groups

Chapter 13.3 Esters

Esters Carboxylic acid react with an alcohol to form an ester The aromas and flavors of many fruits are due to esters Carboxylic Acid Alcohol Ester

Esterification Occurs when a carboxylic acid reacts with an alcohol and is heated in the presence of an acid catalyst (usually H2SO4) In this Reaction, water is produced from the –OH removed from the carboxylic acid and an –H lost by the alcohol

Naming Esters carboxylic acid alcohol Determine the longest carbon chain that belongs to the alcohol (Ethyl – from ethanol) Determine the longest carbon chain that contains the carbonyl and name it as a carboxylic acid (propanoic acid) Change the acid ending from “-ic” to “-ate” (propanoate) Combine the alcohol name followed by the acid name (Ethyl propanoate)

Practice Naming ethyl 3-bromo-2-chloropropanoate ethyl 2-bromopropanoate 3-methylbutyl butanoate

Properties of Esters Esters do not have a hydroxyl (OH) group – so they can not form H-bonds Boiling point is lower than carboxylic acids & alcohols

Acid Hydrolysis of Esters In acid hydrolysis esters are split apart with water when heated in the presence of a strong acid (usually H2SO4 or HCl) The products are carboxylic acid and alcohol This is the reverse of esterification rxn

Base Hydrolysis of Esters In base hydrolysis esters are split apart with heat in the presence of a strong base (usually NaOH or KOH) The products are carboxylic acid salt and alcohol This is called saponification

Base Hydrolysis of Esters The carboxylic acid that is produced in acid hydrolysis is converted in an irreversible reaction to a carboxylate ion by the strong base

Homework Chapter 13 Page 439 13.18 – 13.32 (even)