Macroscale and Microscale Organic Experiments
7th Edition
ISBN: 9781305577190
Author: Kenneth L. Williamson, Katherine M. Masters
Publisher: Brooks Cole
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Chapter 7, Problem 11Q
Write detailed equations showing the mechanism by which aspirin is hydrolyzed in boiling, slightly acidic water.
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Early organic chemists used the Hofmann elimination reaction as the last step of a process known as a Hofmann degradation—a method used to identify amines. In a Hofmann degradation, an amine is methylated with excess methyl iodide in a basic solution, treated with silver oxide to convert the quaternary ammonium iodide to a quaternary ammonium hydroxide, and then heated to allow it to undergo a Hofmann elimination. Once the alkene product is identified, working backward gives the structure of the amine. Identify the amine in each of the following cases: a. 4-Methyl-2-pentene is obtained from the Hofmann degradation of a primary amine. b. 3-Methyl-1-butene is obtained from the Hofmann degradation of a primary amine. c. 2-Methyl-1-3-butadiene is obtained from two successive Hofmann degradations of a secondary amine.
Propose a method to separate a mixture containing phenol, benzoic acid, naphthalene, and p-nitroaniline. Phenol is soluble in sodium hydroxide solution but insoluble in neutral water or sodium bicarbonate solution. Benzoic acid is soluble in either sodium hydroxide or sodium bicarbonate solutions. Write out the structures of the molecules in your scheme.
In an attempt to synthesize compound C through a two-step process, a chemist discovered after
completing the first step that they had inadvertently produced two distinct compounds, A and B.
Upon examining the infrared spectroscopy (IR) results, it was observed that both A and B exhibited
peaks indicative of a ketone and an ester group. Please provide the molecular structures of A and B.
OEt
NaOEt
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A
B
In a chemical experiment, they noticed that both components, A and B, from a combined
sample turned into a new compound, C, during the following stage. The task is to
determine what compound C looks like and explain how compound A or B changes into
compound C through a reaction. Compound C should be the primary molecule
containing carbon created in this process, not just a by-product.
A
B
H3O+, H₂O, A
Mechanism =
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Macroscale and Microscale Organic Experiments
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- The compound acetophenone has a very similar molar mass to that of benzoic acid and benzamide. However, acetophenone has a much lower m.p. (20 °C) than both such that, by contrast, it is a liquid at room temperature. By considering intermolecular forces and comparing functional group structure, account for this big difference in physical properties.arrow_forwardExplain why benzocaine precipitates during the neutralization.arrow_forwardWhat products would result from the following processes? Write an equation for each reaction. a. 2-Methyl-2-butanol is subjected to controlled oxidation. b. 1-Propanol is heated to 140C in the presence of sulfuric acid. c. 3-Pentanol is subjected to controlled oxidation. d. 3-Pentanol is heated to 180C in the presence of sulfuric acid. e. 1-Hexanol is subjected to an excess of oxidizing agent.arrow_forward
- What products would result from the following processes? Write an equation for each reaction. a. 1-Butanol is heated to 140C in the presence of sulfuric acid. b. 1-Butanol is subjected to an excess of oxidizing agent. c. 2-Pentanol is subjected to controlled oxidation. d. 2-Pentanol is heated to 180C in the presence of sulfuric acid. e. 2-Methyl-2-pentanol is subjected to controlled oxidation.arrow_forwardFollowing are the steps in the industrial synthesis of glycerin. Provide structures for all intermediate compounds (AD) and describe the type of mechanism by which each is formed.arrow_forwardGiven a chemical test to distinguish between:(i) Ethane and ethane(ii) Ethanol and ethanoic acid(iii) Soaps and Detergentsarrow_forward
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- illustrate the chemical equation of N,N- Dimethyl aniline reacts with Diazotized Sulfanilic acid to form Methyl Orangearrow_forwardIllustrate the Separation of cyclohexanamine and cyclohexanol by an extraction procedure ?arrow_forwardDescribe or enumerate the step by step process in the laboratory preparation of benzyl alcohol from benzoic acidarrow_forward
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