Experiment 7 Alcohol, Phenols and Ethers 1. Give the balanced equations for all reactions A. Lucas Test a.

ethanol C2H5OH + HCl C2H5Cl + H2O

b. isopropyl alcohol (CH3)2CHOH + HCl c. tert-butanol (CH3)3COH + HCl d. C6H5CH2OH + HCl (CH3)3CCl + ZnCl2 + H2O C6H5CH2Cl + ZnCl2 + H2O (CH3)2CHCl + ZnCl2+ H2O

B. Oxidation of Alcohols a. ethyl alcohol C2H5OH + KMnO4 CH3COOH + H2O + MnO2 + K+ b. isopropyl alcohol 2 (CH3)2CHOH + KMnO4 2 (CH3)2CO + 2 H2O + MnO2 + K c. tert-butyl alcohol (CH3)3COH + KMnO4 NVR d. benzyl alcohol C6H5CH2OH + KMnO4 C6H5COOH + H2O + MnO2 + K+ e. diethyl ether (C2H5)2O + KMnO4 NVR C. Reactions of Phenols a. phenol 1. C6H5OH + 3Br2 C6H5OHBr3 + 3HBr 2. C6H5OH + KMnO4 C6H4O2 + MnO2 + H2O + K+ 3. FeCl3 + 6C6H5OH [Fe(OC6H5)6]3- + 3H+ +3Clb. p-nitrophenol 1. 3 C6H5NO3 + FeCl3 Fe(C6H4NO3)3 + 3 HCl c. p-bromophenol 1. 3 BrC6H5OH + FeCl3 Fe(BrC6H4O)3 + 3 HCl d. b-naphthol 1. 3 C10H7OH + FeCl3 Fe(C10H7O)3+ 3 HCl 2. Explain why the Lucas test is applicable only to alcohols containing 5 or less carbons - This is due to the solubility of the compound in the reagent. A compound with more than six carbons is too large to be dissolved in the reagent and therefore will not react in most cases.

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