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Unformatted text preview: Assignment 8 . Answers 2009 THERE WERE NO QUESTIONS ON THIS ASSIGNMENT DEALING WITH KINETIC AND THERMODYNAMIC ENOLATE FORMATON. You are responsible for this concept in this course. It was discussed carefully in one of the lectures. O O a) O O H b) O c) (-) H (-) H (-) O 1. OH OH a) O b) O O H 2) c Question should have read, when 1b) is treated with chromic acid O O HO d) 3. a) pentanoic acid; b) E-2-pentenoic acid; c) 4-ketopentanoic acid; d) 5-hyydroxy-4- methylpentanoic acid;e) 2-hydroxybenzoic acid; f) phenylethanoic acid [the 2 is not necessary in this case, there is only one possibility!!] ; g) 3,5-dinitrobenzoic acid 4. a) HBr, then Mg in ether, then carbon dioxide and finally acidification with HCl; b) KMnO 4 /NaOH and heat c) FeBr 3 /Br 2 to give para bromomethoxybenzene as a major product, then make the Grignard and add CO 2 ; d) Make the Grignard and add CO 2 . 5. a) Most acidic is 2 chloropentanoic acid. The chloring has a greater affect since it is closer than the fluorine to the acidic function. ; 2 methylpentanoic acid is least acidic. b) Cyclohexane carboxylic acid is most and phenol is least; c) 4 acetyl benzoic acid is most, and 4-methoxybenzoic acid is least acidic. 1 6. FOR ALL OF THESE YOU SHOULD ALSO BE ABLE TO GIVE A MECHANISM. OH O + NaOCH 3 a) b) OH O + NaOCH3 + CH 2 =CH 2 CH 2-I c) OH O Br + NaOH d) CO 2 H + SOCl 2 e) CO 2 H + LiAlH 4 in ether f) CO 2 H + OH H 2 SO 4 g) CO 2 H HO H 2 SO 4 h) CO 2 H + NaBH 4 O(-) Na(+) O O O O O O Cl H 2-OH C O O O O O O(-) Na(+) Not strong enough reducing agent....
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- Fall '10
- Organic chemistry, Trigraph, Carboxylic acid, 4-methoxybenzoic acid, CH3 CH3 H3C, ch lor ob, acetyl benzoic acid