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Alcohols/Reactions Name: ______________________ 1. Predict the major products of the following reactions. a) (R) – 2- butanol + TsCl in pyridine b) (S) – 2-butyl tosylate + NaBr c) Cyclooctanol + CrO3/H2SO4 d) Cyclopentylmethanol + CrO3.pyridine.HCl e) Cyclopentylmethanol + Na2Cr2O7/H2SO4 f) Cyclopentanol + HCl g) Cyclopentanol + H2SO4/heat h) Product from above + OsO4/H2O2 followed by HIO4 i) Sodium methoxide + t-butyl iodide j) Sodium ethoxide + 1-bromobutane Dr. Gupta/Wade/Alcohols-Reactions/Page 1 of 7 2. Predict the major products of dehydration by acid catalysis. a) 1-hexanol b) 2-hexanol c) 3-pentanol d) 1-methylcyclopentanol e) Cyclopentylmethanol f) 2-methylcyclopentanol 3. When 1-cyclohexylethanol is treated with aqueous HBr, the major product is 1-bromo-1ethylcyclohexane. Give a mechanism for the reaction. How would you convert 1-cyclohexylethanol to (1-bromoethyl)-cyclohexane in a good yield? Dr. Gupta/Wade/Alcohols-Reactions/Page 2 of 7 4. Show how you will make each of the following compounds from an alcohol of your choice. a) . b) . c) . d) . e) . f) . g) . h) . i) . Dr. Gupta/Wade/Alcohols-Reactions/Page 3 of 7 5. Predict the major products (including stereochemistry) when (cis)-3-methylcyclohexanol reacts with the following reagents. PBr3 SOCl2 Conc HBr (cis)-3-methylcyclohexanol TsCl/pyridine, then NaBr 6. What simple chemical test can you use to distinguish between the following pairs of compounds? Write the test and the observation. a) 1-butanol and 2-butanol b) 2-butanol and 2-methyl-2-butanol c) Cyclohexanol and cyclohexene 7. How will you synthesize the following compound from compounds of 6 carbons or less? Dr. Gupta/Wade/Alcohols-Reactions/Page 4 of 7 8. Show how you would carry out the following conversions. a) . b) . c) . d) . 9. Predict the esterification products of the following acid/alcohol pairs. a) CH3CH2CH2COOH + CH3OH b) . c) . d) 2CH3CH2OH + H3PO4 e) CH3OH + HNO3 Dr. Gupta/Wade/Alcohols-Reactions/Page 5 of 7 10. Compound A is an optically active alcohol. Treatment with chromic acid converts A to a ketone B. In a separate reaction A is treated with PBr3, converting A to C. Compound D is purified and reacted with magnesium and ether. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis, this solution is found to have 3,4dimethyl-3-hexanol. Propose the structures for A, B and C. PBr3 A H3O+ Mg, ether C Grignard Reagent Na2Cr2O7, H2SO4 D 3,4-dimethyl-3-hexanol B 11. Give the structures of the following products V through Z. PBr3 Cyclopentanol Mg, ether W O || CH3C-Cl i) V X Y Z ii) H3O+ Na2Cr2O7, H2SO4 V 12. Show how you would synthesize the following compounds using alcohols of 4 or less carbons and any other reagents of your choice. a) . b) . Dr. Gupta/Wade/Alcohols-Reactions/Page 6 of 7 c) . d) . e) . f) . 13. Determine the structures A through G in the following scheme. Dr. Gupta/Wade/Alcohols-Reactions/Page 7 of 7