1) Draw the arrows to show bond formation and breaking for the following mechanisms and complete questions b, c, and d. Marking scheme is also provided. (9 marks total) a) All tails of arrows must start at electrons. The arrows must start in the middle of a sigma bond or at a lone pair (2 marks) Take % mark for each mistake until you reach zero. All heads of arrows must end at an atom. (2 marks) Take X mark for each mistake until you reach zero. b) Identify all nucleophiles, electrophiles, acids and bases by circling the word in the figure. (2 marks) Take X mark for each mistake until you reach zero. c) Identity each process as nucleophilic attack, loss of leaving group, proton transfer or carbocation rearrangement (circle in figure). (2 marks) Take X mark for each mistake until you reach zero. d) Label carbocations as primary, secondary or tertiary. (1 mark) Take X mark for each mistake until you reach zero nucleophilic attack loss of leaving group proton transfer carbocation rearrangement H2C-: + H3C-H2C-Br: H3C-H2C-0-CH3 + : Bri Nucleophile Electrophile Nucleophile Electrophile

nucleophilic attack loss of leaving group proton transfer carbocation rearrangement H3C-ö: + H2C-H2C-Br: H3C-H,C-ö-CH3 + Nucleophile Electrophile Nucleophile Electrophile HOC HC H3Cmc-Bri + + S-CH3 H₂C=C-s: нс H3C CH3 H3C/ *C-CH3 H3C? nucleophilic attack loss of leaving group Nucleophile proton transfer Electrophile carbocation rearrangement Nucleophile Electrophile nucleophilic attack loss of leaving group proton transfer carbocation rearrangement + Br носна Br nucleophilic attack loss of leaving group proton transfer carbocation rearrangement nucleophilic attack loss of leaving group proton transfer carbocation rearrangement Nucleophile Electrophile Nucleophile Electrophile nucleophilic attack loss of leaving group proton transfer

Br + Br HOCHZ nucleophilic attack loss of leaving group proton transfer carbocation rearrangement nucleophilic attack loss of leaving group proton transfer carbocation rearrangement Nucleophile Electrophile Nucleophile Electrophile nucleophilic attack loss of leaving group proton transfer carbocation rearrangement acid base Меӧн, X + MECH acid base nucleophilic attack loss of leaving group proton transfer carbocation rearrangement