Question

Mechanism for each reaction

SN2 reaction conditions: To create reaction conditions suitable for an SN2 reaction, sodium iodide will be employed. lodide is a great nucleophile, given its highly polarizable nature. Since SN2 reactions work best in an aprotic solvent, acetone will be utilized for these reactions. As a side product, the sodium cation will form an ionic compound with the leaving halides. Since sodium chloride and sodium bromide is not soluble in acetone, thus the successful substitution reaction of the halides will be confirmed visually by the formation of a salt precipitate. 1. 1-chloroadamantane 2. 3-chloro-1-butene 3. 1-chloro-2-methylpropane

Answer 1

SN? reaction proceeds vis concerted or transition state Same time bond breaking and bond forming happens and nucleophile attacks from back side Nal 7 + NaCl 1- Chloro adamantane is a tertiary alkyl halide, generally it should go SN reaction. But it not react SN because of the bond angles of the carbon where the Cl is attached can not form a planar carbocation. Because the structure of the rest of the molecule will experience a strain. So, it goes via SNC 601, 6- + Na* - -10 - .. 7 + NaCl + Naci Nal 3-Chloro-1-butene allylic can SN reaction via cabocation formation, but in this case some stiric crowding will be there because of same side approch. But in SN2 nucleophile approch from back side, no crowding. So, SN2 goes fast than SN SCI 0 -135-ok.no Na* - + NaCl z La Nalli. Naci 1-Chloro-2-methylpropane SC13 to hom CI + Nat | _ Li. Naci