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ALCOHOLS & PHENOLS PROBLEMS Don’t forget to study the generic functional groups and the common alkyl groups (isobutyl, etc). 1. Name the following compounds using IUPAC and, where possible, common names. a) d) OH H3C HO e) b) HO CH(CH3)2 H2C OH CH3CCH2CH2 OH f) OH CH3 CH CH CH CH3 c) HO CH3 g) OH 2. Draw structures of the following compounds: a) glycerol d) hydroquinone b) m-cresol e) -naphthol c) resorcinol f) allyl alcohol Page 1 ALCOHOLS & PHENOLS PROBLEMS 3. Give IUPAC names and, where possible, common names for the following compounds. a) OH d) CH3 CH2 CH CH2 CH CH3 CH3 HO CH3 e) b) H3C C OH CH3 OH OH Br CH2CHCH2CH2CHCH3 f) c) OH OH OH 4. Draw structures of the following compounds a) isoamyl alcohol d) 2-ethyl-2-buten-1-ol e) trans-2-ethyl-3-methyl-2-penten-1-ol b) 1-cyclopentyl-1-phenyl-2-propanol c) cis-2-iodocyclohexanol f) (E)-1-chloro-1,2-cyclobutanediol Page 2 ALCOHOLS & PHENOLS PROBLEMS 5. Draw the structures of the products of 1-methylcyclohexanol with the following reagents a) OH HBr, H2O CH3 b) Na c) d) H2SO4 cold Na2CrO4, H2SO4, H2O e) PBr3 6. What Grignard and what carbonyl will react to produce the following. Draw structures of all possible combinations. OH C(CH3)2 7. What hydride and what carbonyl will react to produce the following. Draw structures of all possible combinations. CH3 CH3 OH C CH2 CH3 Page 3 ALCOHOLS & PHENOLS PROBLEMS 8. List the reagents needed for the following transformations a) CH3 CH2 b) CH3 CH c) CH3 CH2 CHBr CH CH3 CH3 CH3 CH(OH) CH3 CH3 CH2 CH3 CH CH CH3 CH(OH) CH2 CH3 CHBr CH3 O d) e) CH3 CH2 CH(OH) CH3 CH3 CH2 CH(OH) CH3 f) COOH g) COOH CH3 CH3 CH2 CH2 C CH3 CHCl CH3 COOH CH2OH 9. Number the following compounds in order of acidity, i.e., 1 = most acidic, 4 = least acidic OH COOH OH NO2 Page 4 ALCOHOLS & PHENOLS PROBLEMS 10. Write equations to show how these reactions can be carried out. More than one step may be necessary. There are marks assigned for each intermediate product (not charged transition states) and there are marks for the reagents used; so list them all. No marks are assigned for mechanisms OH a) CH2 CH2 OH CH CH3 b) CH2 c) CH2 CH2OH OH OH CH OH CH3 C CH3 CH3 Page 5 ALCOHOLS & PHENOLS PROBLEMS 11. Write equations to show how the following transformation can be carried out. More than one step may be necessary. There are marks assigned for each intermediate product (not charged transition states) and there are marks for the reagents used; so list them all. No marks are assigned for mechanisms OH CH2CH3 OH 12. For the following reaction: a) Write products for the reaction b) Show the mechanism of the reaction c) Calculate pKeq O H Na+OH- 13. Using arrows, push electrons to show the full mechanism of the reaction shown below. Draw in all lone pairs of electrons on reagents, intermediates and products. Also name CH3 CH3 the type of reaction H3C C O H H Cl H3C C Cl Page 6 ALCOHOLS & PHENOLS PROBLEMS 14. Write products of the following reactions. Show the major product(s) but mechanisms or charged intermediates are not required CH3 a) b) KOH Br H3C PCC in CH2Cl2 CH CH2 OH H3C OH c) Jones Reagent CH CH3 O d) 1. Cl CH3 C H3C CH2 S CH3 O OH H LiAlH4 then 2. + H3O e) Na OH f) PBr 3 OH POCl3 g) CH3CH2CH2CH2OH N: h) H3C SOCl2 CH CH2 OH H3C O i) CH2 CH C 1. LiAlH4 O CH3 + 2. H3O Page 7 ALCOHOLS & PHENOLS PROBLEMS 15. Draw the structures of a Grignard and a carbonyl compound that can be used to synthesize the following alcohols. Show all possible combinations. Also draw the structures of any carbonyl compounds that can be reduced by a LiAlH4 to prepare these compounds a) OH CH2CH3 C CH2CH3 b) OH C H H 16. Write equations to show how the following transformations can be carried out. More than one step may be required. Show all reagents and the products of each step, but do not show any transition states. Mechanisms are not required a) OH OH CH3 b) c) OH O CH3 CH3 O CH2CH3 CH2CH2CH3 Page 8 ALCOHOLS & PHENOLS PROBLEMS 17. Write a mechanism for the following reaction. To write a mechanism, you must show the movement of electrons using arrows. It will be best to redraw the structure showing any lone pairs of electrons and any bonds involved in the reaction. OH H2SO4 C(CH3) 3 CH CH3 (CH3) 2C C(CH3) 2 18. Draw the structure(s) of all reagents which would give the following alcohol when reduced with LiAlH4 (CH3)2CHCH2OH 19. Draw the structures of all sets of reagents that would give the following alcohol when reduced with a Grignard reagent. Show Grignards as well as other reagents. OH CH3CH2CCH2CH3 CH3 20. Draw the formulas or structures of the products of the following reactions ... a) H3C POCl3 OH N b) H3C PBr3 OH H3C cold KMnO4 aqueous OH c) H3C d) hot concentrated HNO3 OH Page 9 ALCOHOLS & PHENOLS PROBLEMS 21. Draw and name the products of this reaction H3C K OH 22. Write equations, including reagents needed to produce the following products. More than one step may be required. Show all steps and the products formed along the way. Do not draw mechanisms or show charged transition states a) CH2CH2OH b) CH2OH Br OH CH2 CH3 OH c) CH2Br CH d) H3C H3C O H3C C C OCH3 C H3C Page 10