UJIAN TENGAH SEMESTER
KIMIA ORGANIK 2
| 1 | Write a structural formula for each one. |
| | a. 5-isopropenyl-2-methyl-2-cyclohexenone b. 4-hydroxy-4-methyl-2-pentanone c. 2-Hydroxypropanoic acid d. 10-Undecenoic acid |
| 2 | a. Predict the product of the reaction of propanal with Sodium cyanide with addition of sulfuric acid b. Predict the product of the reaction of cyclopentanone with Hydrazine c. Give the product of the reaction of pentanoic acid with reagent of Phenylmagnesium bromide d. Give the product of the reaction of 2-(p-Isobutylphenyl)propanoic acid with reagent of Phosphorus tribromide |
| 3 | a. b. c. d. |
| 4
| Wolff–Kishner reduction (hydrazine, KOH, ethylene glycol, 130°C) of the compound shown gave compound A. Treatment of compound A with m-chloroperoxybenzoic acid gave compound B, which on reduction with lithium aluminum hydride gave compound C. Oxidation of compound C with chromic acid gave compound D (C9H14O). Identify compounds A through D in this sequence. |
| 5
| Show by a series of equations how you could synthesize each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents: a. 2-Methylpropanoic acid from tert-butyl alcohol b. HO2C(CH2)5CO2H from HO2C(CH2)3CO2H c. |
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