VJC 2025 Tutorial Questions for RX

1 VICTORIA JUNIOR COLLEGE CHEMISTRY DEPARTMENT Halogen Derivatives (Halogenoalkanes and Halogenoarenes) Tutorial Questions Complete the following tables: (1) Preparation of halogen derivatives Preparation of halogenoalkanes Starting compound Reagents and conditions Product HO CH3 Cl CH3 HCl(g) Preparation of halogenoarenes Cl 2, anhydrous AlCl3 Cl (2) Reactions of halogen derivatives (a) Halogenoalkanes Starting compound Reaction type Reagents and conditions Product CH3CHClCH3 NaOH(aq), heat CH3CH(NH2)CH3 Limited NH3 in ethanol, heat in sealed tube

2 Starting compound Reaction type Reagents and conditions Intermediate Reaction type, reagents and conditions Final product CH3CHClCH3 CH3CH(CN)CH3 Hydrolysis H2SO4(aq), heat CH3CHCH3 CH2NH2 Starting compound Reaction type Reagents and conditions Product (CH3)2CClCH2CH3 NaOH in ethanol, heat (b) Halogenoarenes and vinyl halides Compound Reactivity Br No reaction under normal laboratory conditions. CH3CI=CH2

3 Preparation of Halogenoalkanes 1 State the reagents and conditions needed for the conversion of CH3CH2CH2CH2OH into (a) 1–bromobutane …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. (b) 2–bromobutane (in two steps) …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. Reactions of halogenoalkanes 2 2–bromobutane can react under two different sets of reaction conditions to give two different product mixtures C and D. CH3CHBrCH2CH3 I II C4H10O C4H8 C D (a) State the reagents and conditions necessary for each of the reactions I and II. …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. (b) Product D is a mixture of isomers, all of which decolo urise bromine water. Draw displayed formulae of these isomers and explain the reaction with Br2(aq). …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. ……………………………………………………………………………………………………..

4 (c) State the reagents and conditions for the conversion of CH3CH(Br)CH2CH3 into CH3CH(NH2)CH2CH3. …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. 3 A monocarboxylic acid R occurs in goat’s milk. R has the following composition by mass: C, 62.1%; H, 10.3%; O, 27.6%. Neutralisation of a sample of 0.10 g of R requires 8.6 cm 3 of 0.10 mol dm –3 sodium hydroxide. (a) Determine the molecular formula of R. …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. …………………………………………………………………………………………………….. (b) R can be synthesized in the laborato