Exam 17: Alcohols and Phenols

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hydroquinone or p-dihydroxybenzene or 1,4-benzenediol

Draw: 2,4,6-trinitrophenol

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(E)-2-ethylbut-2-en-1-ol

Exhibit 17-2 Refer to the data below to answer the following question(s). pKas of Some Phenols Exhibit 17-2 Refer to the data below to answer the following question(s). pK<sub>a</sub>s of Some Phenols       -Refer to Exhibit 17-2.Which of the acids in the Table has the weakest conjugate base? Exhibit 17-2 Refer to the data below to answer the following question(s). pK<sub>a</sub>s of Some Phenols       -Refer to Exhibit 17-2.Which of the acids in the Table has the weakest conjugate base? -Refer to Exhibit 17-2.Which of the acids in the Table has the weakest conjugate base?

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Which of the following would be the most acidic?

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Exhibit 17-3 To answer the following question(s), consider the reaction below: Exhibit 17-3 To answer the following question(s), consider the reaction below:   -Refer to Exhibit 17-3.Provide the IUPAC name for the product alcohol. -Refer to Exhibit 17-3.Provide the IUPAC name for the product alcohol.

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Exhibit 17-5 To answer the following question(s),consider the reaction below: Exhibit 17-5 To answer the following question(s),consider the reaction below:   -Refer to Exhibit 17-5.The conversion of an alcohol into an alkyl chloride by reaction with SOC1<sub>2</sub> is an example of: -Refer to Exhibit 17-5.The conversion of an alcohol into an alkyl chloride by reaction with SOC12 is an example of:

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Exhibit 17-6 Consider the Grignard reaction below to answer the following question(s). Exhibit 17-6 Consider the Grignard reaction below to answer the following question(s).   -Refer to Exhibit 17-6.The electrophile in this reaction is: -Refer to Exhibit 17-6.The electrophile in this reaction is:

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Give the IUPAC name for the following compound. Give the IUPAC name for the following compound.

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Explain why nonafluoro-2-methyl-2-propoxide is a much weaker base than tert-butoxide. Explain why nonafluoro-2-methyl-2-propoxide is a much weaker base than tert-butoxide.

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What product is formed when the following substance is treated with CrO3 under appropriate conditions? What product is formed when the following substance is treated with CrO<sub>3</sub> under appropriate conditions?

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Outline the synthetic steps necessary to carry out the conversion below.You may use any organic or inorganic reagents you need.Show the structures of all intermediate compounds that would probably be isolated during the course of your synthesis,and show all necessary reagents. Outline the synthetic steps necessary to carry out the conversion below.You may use any organic or inorganic reagents you need.Show the structures of all intermediate compounds that would probably be isolated during the course of your synthesis,and show all necessary reagents.

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Propose a synthesis of Dimestrol starting from p-methoxypropiophenone as the only source of carbon. Propose a synthesis of Dimestrol starting from p-methoxypropiophenone as the only source of carbon.

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Exhibit 17-4 To answer the following question(s),consider the reaction below: Exhibit 17-4 To answer the following question(s),consider the reaction below:   -Refer to Exhibit 17-4.On the structures provided below,draw arrows which account for the complete stepwise mechanism for this reaction.  -Refer to Exhibit 17-4.On the structures provided below,draw arrows which account for the complete stepwise mechanism for this reaction. Exhibit 17-4 To answer the following question(s),consider the reaction below:   -Refer to Exhibit 17-4.On the structures provided below,draw arrows which account for the complete stepwise mechanism for this reaction.

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Exhibit 17-5 To answer the following question(s),consider the reaction below: Exhibit 17-5 To answer the following question(s),consider the reaction below:   -Refer to Exhibit 17-5.Provide the complete IUPAC name for the starting material in this reaction. -Refer to Exhibit 17-5.Provide the complete IUPAC name for the starting material in this reaction.

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Acid-catalyzed dehydration of 2,2-dimethylcyclohexanol yields 1,2-dimethylcyclohexene as one of the major products.Write the complete stepwise mechanism for this reaction.Show all electron flow with arrows and show all intermediate structures. Acid-catalyzed dehydration of 2,2-dimethylcyclohexanol yields 1,2-dimethylcyclohexene as one of the major products.Write the complete stepwise mechanism for this reaction.Show all electron flow with arrows and show all intermediate structures.

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Draw: 3-methyl-2-buten-1-ol

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​Draw the mechanism of the E2 reaction involving the dehydration of 3-methyl-1-cyclohexanol,when reacting with POCl3 in pyridine.

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Exhibit 17-6 Consider the Grignard reaction below to answer the following question(s). Exhibit 17-6 Consider the Grignard reaction below to answer the following question(s).   -Refer to Exhibit 17-6.The nucleophile in this reaction is: -Refer to Exhibit 17-6.The nucleophile in this reaction is:

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