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1. A solid ester (1) was saponified (SE = 173±1), and the alkaline aqueous solution was evaporated nearly to dryness. The distillate was pure water. 2. The residue was acidified and distilled; a colorless oil (II) was isolated (BP: 202°C). Substance (II) gave a violet color with ferric chloride solution. 3. The residue from the distillation yielded a solid (III) which was alkali soluble. 4. When (III) was heated above its melting point, it changed to (IV). 5. (IV) was dissolved by shaking with warm aqueous alkali, and the solution was acidified; the solid that separated was identical with (III). The ¹H-NMR spectrum of (II) (60 MHz, CD3Cl): S 2.25, 3H, s; & 5.67, 1H, s; S 6.5-7.3, 4H, m. The 85.67 signal had a concentration dependent chemical shift. The ¹H-NMR spectrum of (III) (60 MHz, CD3Cl): 87.4-7.9, m; 8 12.08, s. The singlet had an area one-half that of the multiplet. In addition the chemical shift of the singlet was concentration dependent.
1. Name the functional groups: Substance (II): Substance (III): 2. Which reaction takes place during Substance (III) --> Substance (IV)? ORing ORing Decarboxylation Forming Opening Esterification Saponification Aminolysis Haloform Elimination Substitution Addition 3. What functional group forms during Substance (III) --> Substance (IV)? OEther OEster OAlkene OAlcohol OAnhydride OAmide OAlkyne OCarboxylic Acid
Time left 1:59:09 4: Which reaction takes place during Substance (IV) --> Substance (III)? ODecarboxylation ORing Forming ORing Opening OEsterification OSaponification OAminolysis OHaloform OElimination OSubstitution Addition 5. Determine the structures of Substance (II), (III) and (IV): 1 2 3 OH COOH OH CH₂ 5 8 OH 9 10 11 12 HO COOH OH § ol gee sof CH₂ OH H₂C OH 7 OH
Q6. Assume that you want to investigate the purity of Substance (II) with the help of Gas Chromatography. Would you expect that to require a special preliminary treatment due to its volatility? YES or NO.