Question

2. Three separate reactions are conducted as outlined below. Reaction 1: 4 drops of 1-chlorobutane in 2 mL of 1% AgNO, in ethanol. Reaction 2: 4 drops of 2-chlorobutane in 2 mL of 1% AgNO, in ethanol. Reaction 3:4 drops of t-butyl chloride in 2 mL of 1% AgNO, in ethanol. a. List the expected rate of each of the reactions. List the slowest reaction first and fastest reaction last. b. Explain your reasoning based on substrate structure, the nature of the leaving group (if applicable), and whether the conditions favor Sn1 or Sn2 mechanisms. c. Explain why conditions favor Sn1 or Sw2. d. Identify the nucleophile and leaving group for these reactions. earch

Answer 1

19 mol 2. Reaction1: 4 drops of 4-chlorobetane in 2mL of 17 AgNO3 in eine CH3-CH2 CH2-CH2-4 %. Agnose tot CH ₂ -CH₂ CH₂ - CH2-OCH₂ CH₃ taget Reaction 2 : 4 drops of 2-chlorobufone in AmL of 17.Ag nog in ethano. CH₃-CH2-CH-CH₂ 1%. AgNO3 CH2 - CH3 -CH-CH2 ü Etont' Etort a OCH₂ CH₃ + Aged Reactions: 4drops of t-butylchloride in 2mL of 1% AgNO3 - an ethano. CH3 CHA 1 CH₂-C ca 1% AgNO3 He-C-O CH₂ CH3 + Ageles Et m 2 | (a) Rate of each of the neaction: Reaction-1K Reaction-2 T Reaction -2 , (slowest) .. . (fastest reaction) (C) CHşCH, CH2-CHemel (Renat) CH2 CH3-ÇH-CHg (Rron-2) L 1%. AgNO3 | 14 AgNO3 CH₂=CH2=CH2 Cty tagelt (primang Cantocation) CHg -CH2-CH-CH3 +49412 I cambocation B (2 cabocation intermediate insferomediate) E . - n C, Rxnol và 1) CH₂-C-GO -cac-Ag -8- CH₂ 3 - Carbocation intermediate & Agelt -

+ Ieffect Chacht, ut & , CH₂ - CH₂ H C l 2 deffect only 2-hyper conjugable 5-hypero conjugabond X-H present at atoms present CH3 CH3-2 - CH₂ Here maximum 9 hypers Conjugable 3 7-H presenti cu GHz 3 tsoon Due to the formation of a maximum 9 hypera conjugating Structure as well as the electron donating tIeffect of the methyl group stabilises the tertiary i butyl Cambocation in maximum extend, followed by the 2o and ľ- Cambocation. 1.7. The stability orders of the generated Cambocatimb, 8 Hz to CH = CHz . HB C H Durtala - CH₂ сиз ее Сн, -си-ан-си, сн; си,сна. I . Rate of Substitution reaction will be maximen foro t-butyl chlomide as it undengoes via the I formation of most stable for carbocation inters- mediake. This meaction Conditions favor snt mechanisme via the formation of Cambocation intermediate - (c) Thise substitution reactions are assisted bu Agion (as in AgNO3).

Slow This Ag® ion guides the reaction towards sa pathaway The leaving group a readily home form proccipitation Of Agaye) t and as a result sofrated Sat Carabocation intermediate forms on slow rate limiting step, followed R-a Ago Rotagelse attack by Etant." Le Hactent fast R-%C4ychy - Hey R-O-CH2CH3 (d) for these reactions nucleophile is solvent ethanel molecules Etost. leaving group : chloride call