O-chem - CHM 251 Chapter 11: Reactions of Alcohols 1...

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Unformatted text preview: CHM 251 Chapter 11: Reactions of Alcohols 1 Provide the structure of the major organic product in the reaction below. 2 Provide the structure of the major organic product in the reaction below. No reaction. Tertiary alcohols are not oxidized by PCC. 3 Provide the structure of the major organic product in the reaction below. (CH 3 ) 3 CCH 2 CH 2 OH 2 2 7 2 4 Na Cr O H SO (CH 3 ) 3 CCH 2 CO 2 H 4 Provide the structure of the major organic product in the reaction below. 5 Provide the structure of the major organic product in the reaction below. 6 Chromic acid oxidations are believed to proceed through a chromate ester intermediate. In the oxidation of propran-1-ol, provide the structure of this ester and give the mechanism for its conversion to the intermediate aldehyde. 7 Provide the structure of the major organic product in the reaction below. (CH 3 ) 2 CHCH 2 OH Na (CH 3 ) 2 CHCH 2 O- Na + 8 Provide the structure of the major organic product in the reaction below. 9 Show the most efficient use of the Williamson ether synthesis to prepare CH 3 CH 2 CH 2 OCH(CH 3 ) 2 . 1 (CH 3 ) 2 CHO- Na + + CH 3 CH 2 CH 2 Br 10 The enzyme, alcohol dehydrogenase, which is produced by the liver, converts ethanol to __________, a normal body metabolite. acetic acid 11 Draw the tosylate ion and explain why it is a particularly good leaving group. Extensive resonance stabilization of this ion makes it a particularly good leaving group. 12 Why are alcohols unreactive toward nucleophilic substitution reactions? The hydroxide ion, a relatively strong base, is a very poor leaving group. 13 How can the electrophilicity of alcohols be increased? Suggest several specific ways. The key is to convert the hydroxyl group into a better leaving group. Methods to do this include protonation, conversion to the tosylate ester, and conversion to the halide. 14 Provide the structure of the major organic product in the reaction below. 15 It is necessary to add ZnCl 2 to promote the reaction of HCl with some alcohols while these same alcohols react with HBr quite readily. Explain....
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O-chem - CHM 251 Chapter 11: Reactions of Alcohols 1...

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