chapter12 - 528 Chapter 12 Fuels Organic Chemicals and...

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Chapter 12: Fuels, Organic Chemicals, and Polymers 528 End-of-Chapter Solutions for Chapter 12 Summary Problem Part 1: Answer: see structures below Strategy and Explanation: Given the formula of an alcohol, determine the products of its reaction with KMnO 4 . Use structural formulas to write the reaction between the initial alcohol and the final product of combustion and identify the class of compounds the product falls in. Write an equation for the reaction of the final product of combustion with a base and identify the product’s type, then determine what the product would be if the reaction was basic instead of acidic. If the final product of oxidation reacts with an amine, determine the structural formula and the class of compound formed. Identify if the two reactants in (b) can form a polymer. (a) According to Section 12.5, oxidation occurs with the addition of aqueous KMnO 4 . Oxidation of a primary alcohol produces an aldehyde; oxidation of an aldehyde produces a carboxylic acid: C C C O H H H H H H 8 C C C O O H H H H H 8 H first oxidation product second oxidation product (b) The equation for the reaction of an alcohol and a carboxylic acid is described in Section 12.6: C C C O O H H H H H 8 H + C C C O H H H H H 8 H H H C C C O H H H H H 8 H H C C C O H H H H H 8 (c) The product of the equation in (b) is from the ester class of compounds. (d) The equation for the saponification reaction of an ester with the base, NaOH, is described in Section 12.7, page 575: CH 3 CH 2 CH 2 O 8 H 3 C CH 2 C O 8 + NaOH O H 3 C CH 2 C O 8 - Na + + CH 3 CH 2 CH 2 HO 8 The products are a sodium carboxylate salt and an alcohol. If acidic condition had been used instead of basic condition, saponification as described in Section 12.7, page 574 would occur. The products would be: OH H 3 C CH 2 C O 8 and CH 3 CH 2 CH 2 HO 8
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Chapter 12: Fuels, Organic Chemicals, and Polymers 529 (d) The reaction of a carboxylic acid with an amine forms an amide, as described in Section 12.7 page 586. Using the carcoxylic acid formed in (a) and (CH 3 ) 2 NH, the product has a structural formula that looks like this: C C C O N H H H H H 8 C H H H C H H H This product is from the class of compounds called amides. (f) The alcohol and carboxylic acid used as reactants in (b) cannot be used to form a polymer. As shown in Section 12.7 on page 583, the molecules need to have functional groups on both ends to be able to make a condensation polymer chain. Once the only –COOH and –OH groups in the reactants from (b) are condensed, there’s no way to extend the length of the chain. Part 2: Answer: (a) oxidation (b) converstion of a secondary alcohol adjacent to a –COOH into a ketone (c) C atoms 3 and 4 in first structure, C atom 3 in second structure, C atom 2 in third structure, no chiral centers in fourth structure Strategy and Explanation: Given two specific chemical reactions, identify the general type of reaction in each step, describe what the two steps have in common. Identify the chiral carbon atoms in the structures.
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This note was uploaded on 12/17/2009 for the course CHE 129/130 taught by Professor Hanson during the Spring '09 term at SUNY Stony Brook.

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chapter12 - 528 Chapter 12 Fuels Organic Chemicals and...

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