tb17 - Chaoter 17 - Alcohols and Phenols Draw structures...

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Chaoter 17 - Alcohols and Phenols Draw structures corresponding to the following IUP AC names: 1. cis-4-tert-butylcyclohexanol Answer: (CH3),C-(J-°H 2. 3-methyl-2-buten-I-ol Answer: ~OH 3. 2-phenyl-2-propanol Answer: ox:~ 4. glycerol Answer: OH I HOCHzCHCHzOH 5. 2, 4, 6-trinitrophenol Answer: OH OzN NOz NOz Test Items for McMurry's Organic Chemistry, Seventh Edition 163
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Answer: NOz NOz NOz I I I CHzCHzCHzCHzOH CH3CH3CHzCHOH CH3CHzCHzCHzOH CH3CHCHzCHzOH 3 4 2 11. (CF3hCHOH CH3C C- H (CH3)3COH CH3CHzOH Give acceptable names for each of the following substances. 6. L:°H Answer: (E)-2-ethylbut-2-en-l-ol 7. HOCH2CH2OH Answer: 1, 2-ethanediol or ethylene glycol 8. ~OH Answer: allyl alcohol or 2-propen-l-ol 9. Ho-Q-OH Answer: hydroquinone or p-dihydroxybenzene or l,4-benzenediol Rank 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. NOz I CHzCHzCHzCHzOH NOz I CH3CHCHzCHzOH NOz I CH3CH3CHzCHOH CH3CHzCHzCHzOH Answer: (CF3hCHOH CH3C- C- H 4 (CH3)3COH CH3CHzOH L- 2 164 Chapter 17: Alcolhols and Phenols
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OH OH CH20H C02H B3C~ 12. CN CN CN y l2Ka -H 9.89 m-N02 8.28 P-N02 7.17 m-OCH3 9.65 p-OCH3 10.21 Answer: OH ~ H3CN 3 2 QOH CN 4 QH CN 1 OH Q CN 13. Explain why nonafluoro-2-methyl-2-propoxide is a much weaker base than tert-butoxide. CF3 I u- F C-C-O: 3 I 00 CF3 versus CH3 I 00 H3C- C- 0:- I 00 CH3 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. Refer to the data below to answer the following questions. Y0-°B pKas of Some Phenols 14. The weakest acid in the table is: Answer: p-methoxyphenol 15. Which of the acids in the Table has the weakest conjugate base? Answer: p-nitrophenol Test Items for McMurry's Organic Chemistry, Seventh Edition 165
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a. 1. OsO 4 , pyridine 2. NaHS03, H2O b. 1. Hg(OAc)2'H2O 2. NaBH4 c. 1. RC03H, CH2Cl2 2. H3O+ d. 1. BH3, THF 2. H202, -OH ' 16. How do you account for the difference in acidity between meta and para-nitrophenol? Answer:
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tb17 - Chaoter 17 - Alcohols and Phenols Draw structures...

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