You wish to substitute the bromine in the following molecules with a nucleophile. Explain whether the given molecule would react by S_N 1 or S_N 2 mechanism and explain why. 1-methyl-1-bromo-cyclohexane: S_N 1 mechanism because after Br leaves (leaving group departure) then it is a tertiary carbocation which is favored more in this type of mechanism. 1-bromopropane: This would react by S_N 2 mechanism because it is a primary alkyl halide, which undergo this type of mechanism. Also the nucleophile will be able to attack better because of its structure. 2-bromohexane: S_N 2 mechanism because there is less steric hindrance. Why does benzyl bromide react under both S_N 1 conditions and S_N 2 conditions? It can undergo each condition because in …show more content…
The better the leaving group, the faster the reaction making Br a better leaving group than Cl. Tertiary-butyl iodide reacts faster than tertiary-butyl bromide via S_N 2 mechanism because iodide is a better leaving group than bromide. True or False? True. 1-Chlorobutane (2.5 mL, d=0.886) in 20 mL of acetone is reacted with 90 mL of a 15 wt% solution of NaI in acetone. After work-up, you obtain 1.3 g of 1-iodobutane. Which is the limiting reagent? What is your % yield? Your instructor tells you to make 200 mL of a 1 wt% 〖AgNO〗_3 solution in ethanol, because the stock-room just ran out of the stuff. How would you do this? To promote the S_N 1 mechanism we used 〖AgNO〗_3 in a polar, protic solvent. True of False? Why? True. When the leaving group leaves, it typically makes a negative charge (anion) while the protic solvent is a cation. Electrons can then be donated forming a bond. Also, a strong nucleophile is not necessary in this mechanism. The rate of reaction for the S_N 2 mechanism is dependent on the concentration of both nucleophile and the electrophile. True or False? Justify your