Exam 24: Amines and Heterocycles

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​Draw the mechanism of the reductive amination of 2-butanone in the presence of ammonia and hydrochloric acid.

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Name the following substance.Atoms other than carbon and hydrogen are labeled. Name the following substance.Atoms other than carbon and hydrogen are labeled.

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Exhibit 24-3 Refer to the Table of pKas below to answer the following question(s): pKas of Some Arylammonium Ions Exhibit 24-3 Refer to the Table of pK<sub>a</sub>s below to answer the following question(s): pK<sub>a</sub>s of Some Arylammonium Ions      -Refer to Exhibit 24-3.Explain the difference in acidity between p-aminoanilinium ion and anilinium ion.Use both words and structures. Exhibit 24-3 Refer to the Table of pK<sub>a</sub>s below to answer the following question(s): pK<sub>a</sub>s of Some Arylammonium Ions      -Refer to Exhibit 24-3.Explain the difference in acidity between p-aminoanilinium ion and anilinium ion.Use both words and structures. -Refer to Exhibit 24-3.Explain the difference in acidity between p-aminoanilinium ion and anilinium ion.Use both words and structures.

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Exhibit 24-2 Consider the reaction below to answer the following question(s). Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H2/Ni. Exhibit 24-2 Consider the reaction below to answer the following question(s). Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H<sub>2</sub>/Ni.   -Refer to Exhibit 24-2.Although the yield of methamphetamine is good,some unreacted phenyl-2-propanone remains after the reaction is complete.Describe how methamphetamine can be separated from phenyl-2-propanone. -Refer to Exhibit 24-2.Although the yield of methamphetamine is good,some unreacted phenyl-2-propanone remains after the reaction is complete.Describe how methamphetamine can be separated from phenyl-2-propanone.

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Draw the structures for each of the intermediates in the boxes provided for the synthesis below. Draw the structures for each of the intermediates in the boxes provided for the synthesis below.

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Name: Name:

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Name: Name:

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Describe the importance of the formation of arenediazonium salts.

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Name: Name:

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NaOH,H2O f.HNO3,H2SO4 NaOH,H<sub>2</sub>O f.HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub>

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Name: Name:

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Classify the following amine.Atoms other than carbon and hydrogen are labeled. Classify the following amine.Atoms other than carbon and hydrogen are labeled.

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Exhibit 24-4 Refer to the reaction below to answer the following question(s): Exhibit 24-4 Refer to the reaction below to answer the following question(s):   -Refer to Exhibit 24-4.This reaction is an example of: -Refer to Exhibit 24-4.This reaction is an example of:

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Exhibit 24-3 Refer to the Table of pKas below to answer the following question(s): pKas of Some Arylammonium Ions Exhibit 24-3 Refer to the Table of pK<sub>a</sub>s below to answer the following question(s): pK<sub>a</sub>s of Some Arylammonium Ions      -Refer to Exhibit 24-3.Based on the pK<sub>a</sub>s for their corresponding ammonium ions,which arylamine above is the strongest base? Exhibit 24-3 Refer to the Table of pK<sub>a</sub>s below to answer the following question(s): pK<sub>a</sub>s of Some Arylammonium Ions      -Refer to Exhibit 24-3.Based on the pK<sub>a</sub>s for their corresponding ammonium ions,which arylamine above is the strongest base? -Refer to Exhibit 24-3.Based on the pKas for their corresponding ammonium ions,which arylamine above is the strongest base?

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At which pH will a solution of a 0.00050 M solution of aniline (pKa = 4.63) contain the greatest amount of the neutral species?

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When a THF solution of phenyl-2-propanone and bromobutane is treated with 50% aqueous NaOH,poor yields of 3-phenyl-2-heptanone result.However,when a small amount of benzyltriethylammonium chloride is added to the reaction mixture,the yield of 3-phenyl-2-heptanone increases to 90%.Explain these results. When a THF solution of phenyl-2-propanone and bromobutane is treated with 50% aqueous NaOH,poor yields of 3-phenyl-2-heptanone result.However,when a small amount of benzyltriethylammonium chloride is added to the reaction mixture,the yield of 3-phenyl-2-heptanone increases to 90%.Explain these results.

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Exhibit 24-8 Refer to the data below to answer the following question(s): Triclocarban is a disinfectant prepared from 3,4-dichloroaniline and 4-chlorophenylisocyanate. Exhibit 24-8 Refer to the data below to answer the following question(s): Triclocarban is a disinfectant prepared from 3,4-dichloroaniline and 4-chlorophenylisocyanate.   -Refer to Exhibit 24-8.Prepare 3,4-dichloroaniline from benzene.  -Refer to Exhibit 24-8.Prepare 3,4-dichloroaniline from benzene. Exhibit 24-8 Refer to the data below to answer the following question(s): Triclocarban is a disinfectant prepared from 3,4-dichloroaniline and 4-chlorophenylisocyanate.   -Refer to Exhibit 24-8.Prepare 3,4-dichloroaniline from benzene.

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The pKa of diethylammonium ion is 10.98.What is the pKb of diethylamine?

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Exhibit 24-2 Consider the reaction below to answer the following question(s). Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H2/Ni. Exhibit 24-2 Consider the reaction below to answer the following question(s). Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H<sub>2</sub>/Ni.   -Refer to Exhibit 24-2.Identify the nucleophile in the initial reaction of phenyl-2-propanone to yield intermediate A. -Refer to Exhibit 24-2.Identify the nucleophile in the initial reaction of phenyl-2-propanone to yield intermediate A.

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Exhibit 24-2 Consider the reaction below to answer the following question(s). Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H2/Ni. Exhibit 24-2 Consider the reaction below to answer the following question(s). Methamphetamine can be synthesized by reacting phenyl-2-propanone with methylamine in the presence of H<sub>2</sub>/Ni.   -Refer to Exhibit 24-2.Intermediate A is an example of: -Refer to Exhibit 24-2.Intermediate A is an example of:

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