Chapter 17 - Alcohols and PhenolsDrawing Instructions: Draw structures corresponding to each of the given names.1. Draw: cis-4-tert-butylcyclohexanolANSWER: POINTS: 12. Draw: 3-methyl-2-buten-1-olANSWER: POINTS: 13. Draw: 2-phenyl-2-propanolANSWER: POINTS: 14. Draw: glycerolANSWER: POINTS: 15. Draw: 2, 4, 6-trinitrophenolANSWER: POINTS: 1IUPAC Naming Instructions: Provide proper IUPAC names.6. Name:ANSWER: (E)-2-ethylbut-2-en-1-olPOINTS: 17. Name:Cengage Learning Testing, Powered by Cognero Page 1Chapter 17 - Alcohols and PhenolsHOCH2CH2OHANSWER: 1, 2-ethanediol or ethylene glycolPOINTS: 18. Name:ANSWER: allyl alcohol or 2-propen-1-olPOINTS: 19. Name:ANSWER: hydroquinone or p-dihydroxybenzene or 1,4-benzenediolPOINTS: 1Exhibit 17-1Rank the following groups of compounds from most acidic (1) to least acidic (4). Place the number corresponding to the compound's relative rank in the blank below the structure.10. ANSWER: POINTS: 111. ANSWER: POINTS: 1Cengage Learning Testing, Powered by Cognero Page 2Chapter 17 - Alcohols and Phenols12. ANSWER: POINTS: 113. Explain why nonafluoro-2-methyl-2-propoxide is a much weaker base than tert-butoxide.ANSWER: Nonafluoro-2-methyl-2-propoxide anion is more stable than tert-butoxide anion because the electron-withdrawing fluoride atoms inductively delocalize the negative charge. Since nonafluoro-2-methyl-2-propoxide is more stable than tert-butoxide, it is a weaker base.POINTS: 1Exhibit 17-2Refer to the data below to answer the following question(s).pKas of Some PhenolsYp Ka −H9.89 m-NO28.28 p-NO27.17 m-OCH39.65 p-OCH310.2114. Refer to Exhibit 17-2. The weakest acid in the table is:ANSWER: p-methoxyphenolPOINTS: 115. Refer to Exhibit 17-2. Which of the acids in the Table has the weakest conjugate base?Cengage Learning Testing, Powered by Cognero Page 3Chapter 17 - Alcohols and PhenolsANSWER: p-nitrophenolPOINTS: 116. Refer to Exhibit 17-2. How do you account for the difference in acidity between meta and para-nitrophenol?ANSWER: In m-nitrophenol, the inductive effect of the electron-withdrawing nitro group helps to stabilize the negative charge on oxygen. However, when the nitro group is para to the oxygen, direct conjugation of the negative charge on oxygen with the nitro group can occur. p-Nitrophenolate ion is, thus, more stable than m-nitrophenolate ion, and, as a result, forms more readily.POINTS: 1Exhibit 17-3To answer the following question(s), consider the reaction below:17. Refer to Exhibit 17-3. The best reagents for accomplishing the above transformation are:a. 1.OsO4, pyridine 2.NaHSO3, H2Ob. 1.Hg(OAc)2, H2O 2.NaBH4c. 1.RCO3H, CH2Cl2 2.H3O+d. 1.BH3, THF 2.H2O2, −OHANSWER: dPOINTS: 118. Refer to Exhibit 17-3. The alcohol product is classified as a:a.1° alcoholb.2° alcoholc.3° alcohold.4° alcoholANSWER: bPOINTS: 119. Refer to Exhibit 17-3. On the templates provided below, draw both conformations of the alcohol product. Circle the least stable conformation.Cengage Learning Testing, Powered by Cognero Page 4Chapter 17 - Alcohols and PhenolsANSWER: POINTS: 120. Refer to Exhibit 17-3. Provide the IUPAC name for the product alcohol.ANSWER: trans-2-MethylcyclohexanolPOINTS: 1Exhibit 17-4To answer the following question(s), consider the reaction below:21. Refer to Exhibit 17-4. On the structures provided below, draw arrows which account for the complete stepwise mechanism for this reaction.ANSWER: POINTS: 122. Refer to Exhibit 17-4. The dehydration of secondary and tertiary alcohols by reaction with POCl3 in pyridine is an example of:a. an E1 processb.an SN1 processc. an E2 processCengage Learning Testing, Powered by Cognero Page 5Chapter 17 - Alcohols and Phenolsd.an SN2 processANSWER: cPOINTS: 123. Refer to Exhibit 17-4. Why is 3-methylcyclohexene the major product of this reaction instead of 1-methycyclohexene?ANSWER: In E2 elimination, dehydration proceeds most readily when the two groups to be eliminated have a trans-diaxial relationship. In this compound, the only hydrogen with the proper geometric relationship to the −OH group is at C6 so the major product of this reaction is 3-methylcyclohexene.POINTS: 124. 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.ANSWER: POINTS: 1Exhibit 17-5To answer the following question(s), consider the reaction below:25. Refer to Exhibit 17-5. Provide the complete IUPAC name for the starting material in this reaction.ANSWER: (R)-2-heptanolPOINTS: 126. Refer to Exhibit 17-5. The starting material can be classified as a:a.1° alcoholb.2° alcoholc.3° alcohold.4° alcoholCengage Learning Testing, Powered by Cognero Page 6Chapter 17 - Alcohols and PhenolsANSWER: bPOINTS: 127. Refer to Exhibit 17-5. Write the complete stepwise mechanism for the reaction. Show all intermediates and all electronflow with arrows.ANSWER: POINTS: 128. Refer to Exhibit 17-5. The conversion of an alcohol into an alkyl chloride by reaction with SOC12 is an example of:a. an E1 processb.an SN1 processc. an E2 processd.an SN2 processANSWER: dPOINTS: 1Exhibit 17-6Consider the Grignard reaction below to answer the following question(s).29. Refer to Exhibit 17-6. The electrophile in this reaction is:ANSWER: BPOINTS: 130. Refer to Exhibit 17-6. The nucleophile in this reaction is:ANSWER: APOINTS: 131. Refer to Exhibit 17-6. The alcohol product can be classified as a:Cengage Learning Testing, Powered by Cognero Page 7Chapter 17 - Alcohols and Phenolsa.1° alcoholb.2° alcoholc.3° alcohold.4° alcoholANSWER: cPOINTS: 1Exhibit 17-7A highly useful and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonyl compounds. Show what Grignard reagent and what carbonyl compound you would start with to prepare each alcohol below. List all possibilities.32. ANSWER: POINTS: 133. ANSWER: POINTS: 134. Cengage Learning Testing, Powered by Cognero Page 8Chapter 17 - Alcohols and PhenolsANSWER: POINTS: 135. ANSWER: POINTS: 1Exhibit 17-8Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.36. ANSWER: POINTS: 137. ANSWER: POINTS: 138. Cengage Learning Testing, Powered by Cognero Page 9Chapter 17 - Alcohols and PhenolsANSWER: