Esters By Cori and Shania

What Are Esters?  Esters are derivatives of carboxylic acids where the –OH of the carboxyl group has been replaced by an –OR from an alcohol. Esters also contain a carbonyl group and an ether link to the carbonyl carbon. (Wilbraham, 742) ( We will futher explain this during esterification… don’t worry!!!)  Esters are derivatives of carboxylic acids where the –OH of the carboxyl group has been replaced by an –OR from an alcohol. Esters also contain a carbonyl group and an ether link to the carbonyl carbon. (Wilbraham, 742) ( We will futher explain this during esterification… don’t worry!!!)

But first of all… Where are they found? Naturally occurring In fruit Animal fats (2Clark, 2) Vegetable oils (2Clark, 2) Flowers (Wilbraham, 742) Naturally occurring In fruit Animal fats (2Clark, 2) Vegetable oils (2Clark, 2) Flowers (Wilbraham, 742) Other common household products that contain esters are… Cosmetic (Marked, 1) Drinks and food (Choppin, 625) Artificial smell and flavouring (choppin 625) Soaps and Shampoos (Marked,1) Perfumes (Wilbraham, 742) (Thorne, 1) (Detergents,1)(Romero, 1)

General structure for esters c O R’ R Alkyl group (Alcohol) Carbonyl group (Acid part) Double bond between carbon and oxygen o (Education,1) (BBC, 1) FYI: The R groups can be short-chain or long-chain aliphatic alkyl or aromatic (aryl) groups or saturated or non saturated. (Wilbraham, 742)

Naming esters 101 These are the rules… Two worded names Alkyl group R’ (alcohol) is the first part of the name Second word is adding OATE to the stem of the acid name. (Richard 1) To name esters properly, their structural formula must be read backwards. ( Choppin 625) Examples of naming… C O O CH ₂ -CH ₃ CH ₃ Ethyl ethanoate C CH ₂ - CH ₂ -CH ₃ H Propyl methanoate CH ₃ CH ₃ -CH ₂ -CH ₂ Methyl butanoate CH ₂ - CH ₂ -CH ₃ CH ₃ Propyl ethanoate (CLARK,1) (2Clark,4)

Furthering your ester naming knowledge! Ethyl benzoate O C O CH ₂ -CH ₃ (2015, 3) C O O CH ₂ -CH ₂ -CH ₃ Propyl benzoate (TCI, 1) O C O CH ₃ -CH ₂ -CH ₂ -CH ₂ Cyclohexyl hexanoate

Esterfication synthesis To synthesize an ester, heat a carboxylic acid along with an alcohol or a phenol; an acid catalyst must be added as well. The oxygen of the alcohol adds to the carboxyl group, splitting out a molecule of water in the process. The reaction is reversible, meaning it often reaches an homeostasis state with a large amount of unreacted starting material still present. (Seager, 23) To synthesize an ester, heat a carboxylic acid along with an alcohol or a phenol; an acid catalyst must be added as well. The oxygen of the alcohol adds to the carboxyl group, splitting out a molecule of water in the process. The reaction is reversible, meaning it often reaches an homeostasis state with a large amount of unreacted starting material still present. (Seager, 23)

Esterification example CH ₃ C O OH CH ₃ CH ₂ O H H+ CH ₃ C O OCH ₂ CH ₃ H₂OH₂O Ethanoic acidEthanol Ethyl ethanoate Water (Wilbraham, 743)

Properties of esters Some properties of esters include… A fruity fragrance (Choppin 625) A boiling point of 77.1 ◦C (2Clark, 4) Small chained esters are soluble in water (polar) (2clark, 4) Larger chained esters are soluble in alcohol and are limited in term of solubility (choppin, 625)(Wilbraham, 742) Clear, colourless liquid (choppin, 625) Some properties of esters include… A fruity fragrance (Choppin 625) A boiling point of 77.1 ◦C (2Clark, 4) Small chained esters are soluble in water (polar) (2clark, 4) Larger chained esters are soluble in alcohol and are limited in term of solubility (choppin, 625)(Wilbraham, 742) Clear, colourless liquid (choppin, 625)

So you think you know esters? Take one of the netbooks provided to your group Close your notes, no cheating ;) Use the link provided below: Rules… Answer ten questions on esters, through multiple choice and true or false questions. Please raise your hand when you have completed the quiz; we will then come around and write down your mark. For participating, you will win an “estery” treat. Good luck!!! Take one of the netbooks provided to your group Close your notes, no cheating ;) Use the link provided below: Rules… Answer ten questions on esters, through multiple choice and true or false questions. Please raise your hand when you have completed the quiz; we will then come around and write down your mark. For participating, you will win an “estery” treat. Good luck!!!

Picture References.  Thorne, Alyssa. Carly Alyssa Thorne. WhatTypeofdecisionmakerareyou Google image search. Web. 27 September  Unknown author. Detergents and soaps. Soaps&detergents-Ingredients Google image search. Web. 27 September  Romero, Vanessa. Healthy Living How To. ReaderQ&A-WhatCosmeticsDoYouUse Google image search. Web. 27 September  Unknown author. Mcat-review. OxygenContainingCoupounds-Alcohols Google image search. Web. 27 September  Unknown author. BBC. Namingorganiccompounds Google Search. Web. September  Thorne, Alyssa. Carly Alyssa Thorne. WhatTypeofdecisionmakerareyou Google image search. Web. 27 September  Unknown author. Detergents and soaps. Soaps&detergents-Ingredients Google image search. Web. 27 September  Romero, Vanessa. Healthy Living How To. ReaderQ&A-WhatCosmeticsDoYouUse Google image search. Web. 27 September  Unknown author. Mcat-review. OxygenContainingCoupounds-Alcohols Google image search. Web. 27 September  Unknown author. BBC. Namingorganiccompounds Google Search. Web. September

Information References  Richard, James. 3 rd IntroductiontoEsters. Revised Google search. Web. 24 September  Choppin, Gregory, et Al. Chemistry: Science of Matter, Energy, And Change. Silver Burdett Company, Print.  Unknown author. Education Scotland. Makingesters. Google search. Web. 24 September  Clark, Jim. Chem guide. IntroducingEsters. Google search. Web. 26 Sepember  Seager, Spencer. Chtf.Stuba.sk. CarboxylicAcidsandEsters. Google search. Web. 26 September  Unknown author. Marked by Teachers. WhatanEsteris,Howitismade,examplesofesters,animaltesingissues,andethics Google Search. Web. September  Clark, Jim. Chem Wiki. PropertiesofEsters. Google Search. Web. September  Wilbraham, Antony et Al. Prentice Hall Chemistry. Pearson Education Inc, Print.  Unknown author. 2012books.lardbucket. 15.6Esters:StructuresandNames. Google image search. Web. September  Unknown author. TCI America. Propylbenzoate. Google image search. Web. September  Unknown author. Pubchem. Cyclohexylhexanoate. Google image search. Web. September  Richard, James. 3 rd IntroductiontoEsters. Revised Google search. Web. 24 September  Choppin, Gregory, et Al. Chemistry: Science of Matter, Energy, And Change. Silver Burdett Company, Print.  Unknown author. Education Scotland. Makingesters. Google search. Web. 24 September  Clark, Jim. Chem guide. IntroducingEsters. Google search. Web. 26 Sepember  Seager, Spencer. Chtf.Stuba.sk. CarboxylicAcidsandEsters. Google search. Web. 26 September  Unknown author. Marked by Teachers. WhatanEsteris,Howitismade,examplesofesters,animaltesingissues,andethics Google Search. Web. September  Clark, Jim. Chem Wiki. PropertiesofEsters. Google Search. Web. September  Wilbraham, Antony et Al. Prentice Hall Chemistry. Pearson Education Inc, Print.  Unknown author. 2012books.lardbucket. 15.6Esters:StructuresandNames. Google image search. Web. September  Unknown author. TCI America. Propylbenzoate. Google image search. Web. September  Unknown author. Pubchem. Cyclohexylhexanoate. Google image search. Web. September