Which S_(N)1 reaction would you expect to take place more rapidly ? (a) (i) (CH_(3))_(3)C Cl+H_(2)O to (CH_(3))_(3)COH+HCl Or (ii) (CH_(3))_(3)C Br+H_(2)O to (CH_(3))_(3)COH+HBr (b) (i) (CH_(3))_(3)C Cl+H_(2)O to (CH_(3))_(3)COH + HCl Or (ii)C_(5)H_(5)Cl+H_(2)O to C_(5)H_(5)OH + HCl (c) (i) (CH_(3))_(3)C Cl+ H_(2)O to (CH_(3))_(3)COH + HCl Or (ii) (CH_(3))_(3)C Cl+ CH_(3)OH to (CH_(3))_(3)COCH_(3)+ HCl (d) (i)(CH_(3))_(3)C Cl(1.0M)+CH_(3)CH_(2)O^(-)(1.0M) overset(C_(2)H_(2)OH)to (CH_(3))_(3)COCH_(2)CH_(3)+Cl^(-) Or (ii) (CH_(3))_(3)C Cl(1.0M)+CH_(3)CH_(2)O^(-)(2.0M) overset(C_(2)H_(2)OH)to (CH_(3))_(3)COCH_(2)CH_(3)+Cl^(-)

Which S_(N)1 reaction would you expect to take place more rapidly ? (

1.	Which S_(N)1 reaction would you expect to take place more rapidly ? (a) (i) (CH_(3))_(3)C Cl+H_(2)O to (CH_(3))_(3)COH+HCl Or (ii) (CH_(3))_(3)C Br+H_(2)O to (CH_(3))_(3)COH+HBr (b) (i) (CH_(3))_(3)C Cl+H_(2)O to (CH_(3))_(3)COH + HCl Or (ii)C_(5)H_(5)Cl+H_(2)O to C_(5)H_(5)OH + HCl (c) (i) (CH_(3))_(3)C Cl+ H_(2)O to (CH_(3))_(3)COH + HCl Or (ii) (CH_(3))_(3)C Cl+ CH_(3)OH to (CH_(3))_(3)COCH_(3)+ HCl (d) (i)(CH_(3))_(3)C Cl(1.0M)+CH_(3)CH_(2)O^(-)(1.0M) overset(C_(2)H_(2)OH)to (CH_(3))_(3)COCH_(2)CH_(3)+Cl^(-) Or (ii) (CH_(3))_(3)C Cl(1.0M)+CH_(3)CH_(2)O^(-)(2.0M) overset(C_(2)H_(2)OH)to (CH_(3))_(3)COCH_(2)CH_(3)+Cl^(-)
Answer» Solution :(a) Reaction (II) because `Br^(-)` ION is a better leaving group than `Cl^(-)` ion, (b) Reaction (i) because the reactant is a tertiary halide. MOREOVER, phenyl HALIDES are not reactive in `S_(N)1` reactions. (c) Reaction (i) because water is more polar solvent than methanol and `S_(N) 1` reaction takes place faster in more polar solvent. (d) Both reactions occur at the same rate because `S_(N)1` reactions are independent of the concentration of the NUCLEOPHILE.