Solve the structure of unknown organic compound X based on thefollowing data: a.

Question

Solve the structure of unknown organic compound X based on thefollowing data: a. Element analysis: C 66.63% H 11.18% O 22.19% Formula weight72.11g/mol b. Lucas test: positive c. chromic acid test: positive d. Br2/CH2Cl2 test: positive e. Pure X is optically active f. IR 3390 cm-1 broad peak Solve the structure of unknown organic compound X based on thefollowing data: a. Element analysis: C 66.63% H 11.18% O 22.19% Formula weight72.11g/mol b. Lucas test: positive c. chromic acid test: positive d. Br2/CH2Cl2 test: positive e. Pure X is optically active f. IR 3390 cm-1 broad peak

Explanation / Answer

If we assume that there is 100g of substance ispresent.Then we take the given percents as weights for individualatoms. Therefore the number of moles of C present = weight ofC/molar weight                                                                    = 66.63g/12g/mole                                                                    = 5.55 mole Number of moles of Hpresent                    = 11.18g/1g/mole                                                                    = 11.18mole number of moles of Opresent                     = 22.19g/16g/mole                                                                    = 1.3868 mole Therefore                                 C                           H                           O                           5.55mole                 11.18mole               1.38mole                   5.55mole/1.38mole        11.18mole/1.38mole    1.38mole/1.38mole                                 4                                 8                          1 Thus empirical formula of the compound  = C4H8O1 By consider the molar weight we conclude that this isthe molecular mass of the compound It gives the Lucas test thus It would be aalcohol. It reacts with cromic acid and gives the positivetest. The Br2/CH2Cl2 positive test indicates that itcontains a double bond. Optical activity indicates the presence of chiralcarbon. The broad peak at 3390cm-1 indicates thepresence of -OH group. From the above information, the structure of Xis                    CH2=CH-CH(CH3)-OH By consider the molar weight we conclude that this isthe molecular mass of the compound It gives the Lucas test thus It would be aalcohol. It reacts with cromic acid and gives the positivetest. The Br2/CH2Cl2 positive test indicates that itcontains a double bond. Optical activity indicates the presence of chiralcarbon. The broad peak at 3390cm-1 indicates thepresence of -OH group. From the above information, the structure of Xis                    CH2=CH-CH(CH3)-OH                           

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