Organic Reactions. Recognize organic reactions: substitution, addition, esterification, combustion, fermentation, and saponification.
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1 Why? Organic Reactions Many organic reactions lead to products we use everyday. Organic reactions can be categorized by looking at the reactants used and the products formed. Soap, alcohol, fragrances, flavors and flames in your barbeque are all products of organic reactions. Learning Objectives Recognize organic reactions: substitution, addition, esterification, combustion, fermentation, and saponification. Success Criteria Predict the products of organic reactions. Vocabulary substitution, addition, fermentation, saponification, combustion, esterification Prerequisites Writing chemical equations Ability to distinguish reactants and products in a reaction Naming and identifying organic compounds Ability to distinguishing between saturated and unsaturated hydrocarbons Naming and recognizing functional groups in organic compounds
2 Model #1: Substitution H H H H H C C H + Cl Cl H C C H + H Cl H H H Cl ethane + chlorine chloroethane hydrogen chloride 1. What are the reactants and products in this reaction? 2. Describe what happened in the substitution reaction. 3. What are the characteristic features of a substitution reaction? Exercises 1. Draw and name the products of the substitution reaction between methane and bromine. H Η C Η + Br Βr H Methane + Bromine 2. Describe what happens in the substitution reaction that involves methane and bromine molecules.
3 Organic Reactions 3. Describe a substitution reaction in general terms. Model # 2: Addition H H H H H H H H H C -C -C = C -Η + Cl -Cl Η -C --C C -C -Η H H H H Cl Cl 1- butene + chlorine 1,2 - dichlorobutane 1. How are the reactants in this reaction the similar to those in the substitution reaction? 2. How are the reactants in this reaction different from those in the substitution reaction? 3. What type of compound is the reactant in the addition reaction? 4. Describe what happens in the addition reaction.
4 5. What are the characteristic features of an addition reaction? 6. Suggest at least two other diatomic elements be could replace chlorine in an addition reaction. Exercises 1. Draw and name the products of the addition reaction between pentene and hydrogen. H H H H C C = C C C H + H H H H H H H Pentene + Hydrogen 2. Describe what is going on between the molecules of pentene and hydrogen in this addition reaction. 3. Describe an addition reaction in general terms.
5 Organic Reactions Model 3: Combustion C 3 H 8 + O 2 CO 2 + H 2 O propane + oxygen carbon dioxide + water 1. What are the reactants and products in this reaction? 2. Describe what happened in the combustion reaction. 3. What are the characteristic features of a combustion reaction? Exercise 1. Propane is an alkane, hexene is an alkene, and butyne is an alkyne. What would be the products of the combustion equation for each of these compounds? Explain your answer. 2. Write the balanced equation for the complete combustion of hexene (C6H12). 3. Describe a combustion equation in general terms.
6 Model 4: Esterification Many compounds found in fruits can be prepared in the laboratory using an esterification reaction. H O H H H H O H H H H C C OH + HO C C C H H C C O C C C H + HOH H H H H H H H H H ethanoic acid + propyl alcohol propylethoanoate + water 1. To what class of organic compounds does reactant 1 belong? 2. To what class of organic compounds does reactant 2 belong? 3. To what class of organic compounds does the product (not water) belong? 4. Based on the information in the model, what are the characteristic features of an esterification reaction? Exercise 1. Draw a structural formula for each of the reactants in the reaction below. butanoic acid + 1-pentanol X + water 2. Identify and draw product X.
7 Organic Reactions 3. In general terms, describe an esterification equation. Model #5: Fermentation Yeast/zymase C 6 H 12 O 6 2C 2 H 5 OH + 2CO 2 Sugar ethanol carbon dioxide 1. Ethanol is an example of what type of organic compound? 2. What is the role of the yeast/zymase in the fermentation reaction? Exercise 1. What are the characteristic features of a fermentation reaction?
8 Model #6: Saponification C 3 H 5 (C 17 H 35 COO) 3 + 3NaOH 3 C 17 H 35 COO - Na + + C 3 H 5 (OH) 3 Fat Strong Soap Glycerin Base 1. Draw the structural formula for one soap molecule. 2. Draw the structural formula for glycerin. Exercise 1. What are the characteristic features of a saponification reaction? 2. If the Na + in the soap molecule were to be replaced with H+, what would be the classification of the organic compound that forms?
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