Question

Identify the correct compound(s) in each case. Explain your choice A compound believed to be either diethyl ether or propyl alcohol is miscible in water a) b) A compound believed to be either allyl methyl ether or propyl alcohol decolorizes a solution of Br, in CH,C c) Four stereoisomeric compounds C,HO, all optically active, contain no double bonds and evolve a gas when treated with CHMgl d) A compound believed to be either cyclohexyl methyl ether or 2-methylcyclohexanol evolves a gas when treated with NaH Arrange these compounds in order of increasing solubility in water. Explain. QH OH HO 4 1 2

Answer 1

a) A compound believed to be either diethyl ether or propyl alcohol is miscible in water. Between diethyl ether and propyl alcohol, propyl alcohol can form hydrogen bonding with water and hence it is miscible in water. diethyl ether propyl alcohol con LO-H hydrogen bonding b) A compound believed to be either allyl methyl ether or propyl alcohol decolorizes a solution of Br2 in CH2C12 B12 Br allyl methyl ether - OBr allyl methyl ether decolorizes bromine in CH2Cl2 since it has a double bond in it. Alkenes undergo electrophilic addition reaction to give dibromo compound as shown above.

c) Four stereoisomeric compounds C3H30, all optically active, contain no double bonds and evolve a gas when treated with CH3Mgl. OH Chemical Formula: C3H30 OH Chemical Formula: C3H2O Chemical Formula: C3H2O Only alcohol compounds react with CH3Mgl and evolve hydrogen gas d) A compound believed to be either cyclohexyl methyl ether or 2-methylcyclohexanol evolves a gas when treated with NaH. cyclohexyl methyl ether 2-methylcyclohexanol OH Alcohol compounds react with NaH react with and evolve hydrogen gas, hence 2- methylcyclohexanol is correct option.

We know that, polar compounds are soluble in polar solvents (water in the present case) & non-polar compounds dissolve in non-polar solvents. 2. More H-bonding, more soluble due to two -OH group. 5. less soluble than 2 due to presence of one -OH group. 3. Non-polar compound, least soluble in water. Solubility = 3 <1<5<4 <2 Arrange these compounds in order of increasing solubility in water. Explain. m plynom