RI Organic Remedial

Name: ………………………………………. ( ) Class: ……………. Date: ……………. Raffles Institution Year 6 H2 Chemistry 2025 Set A T2W7 – Halogen Derivatives, Hydroxy and Carbonyl Compounds Notes: Nucleophilic substitution mechanisms  Pre-ChemFocus Activity  • Familiarise yourself with the following mechanisms: Nucleophilic Substitution (SN1, SN2), Nucleophilic Addition • To view infopack at IVY > C2025 – H2 CHEMISTRY > Pages > [ChemFocus] Y6 T2W7 Halogen Derivatives, Hydroxy and Carbonyl Compounds > FIRST VIDEO

Self-Check Questions 1 When an optically pure solution containing 2 -chlorobutane reacts with NaCN under alcoholic conditions, the resulting solution was optically active. 2-chlorobutane Cl + CN - CN Cl -+ (a) A description of the reaction mechanism is illustrated below. Circle and annotate on the diagram to indicate how the mechanism is drawn incorrectly. C Cl CH3 H CH2CH3 δ-δ+ - CN NC C Cl CH3 H CH2CH3 C H CH3 NC CH2CH3 Cl - Learning points: (b) 2-chloro-2-methylbutane also undergoes nucleophilic substitution reaction with NaCN under alcoholic conditions. However, the overall order of reaction was found to be 1 instead of 2. Explain why. ……………………………………………………………………………………………….. ……………………………………………………………………………………………….. ……………………………………………………………………………………………….. ……………………………………………………………………………………………….. ……………………………………………………………………………………………..[2] Check your answers at IVY > C2025 – H2 CHEMISTRY > Pages > [ChemFocus] Y6 T2W7 Halogen Derivatives, Hydroxy and Carbonyl Compounds > Remaining videos

2 (a) In the boxes A to F below, draw the structural formula of organic compounds formed. (b) In the table below, suggest the reagents and conditions for reactions (i) to (vi). Reaction Reagents and Conditions (i) (ii) (iii) (iv) (v) (vi) CH3CH2O-Na+ heat F B CH3CH2CH2OH CH3CH(OH)CH3 C E LiAlH4, dry ether Or H2, Ni, heat limited Br2 uv light KOH (aq) heat (v) A (ii) (iii) D CH3CH2CH2NH2 (iv) (i) KCN in ethanol, heat CH3CH2CH2Br CH3CO2H (vi)

3 Mark with a ( ✓) if the following compounds gives a positive test with each of the following chemical test. O 2,4-dinitrophenylhydrazine Fehling’s solution, heat Tollens’ reagent, heat I2(aq), NaOH(aq), heat O 2,4-dinitrophenylhydrazine Fehling’s solution, heat Tollens’ reagent, heat I2(aq), NaOH(aq), heat OH 2,4-dinitrophenylhydrazine Fehling’s solution, heat Tollens’ reagent, heat I2(aq), NaOH(aq), heat O 2,4-dinitrophenylhydrazine Fehling’s solution, h