Give the product of each of the following substitution reactions. Which of these transformations should proceed faster in a polar, aprotic solvent (such as acetone or DMSO) than in a polar, protic solvent (such as water or CH,OH)? Explain your answer on the basis of the mechanism that you expect to be operating in each case.
(a) CH3CH2CH2Br + Na+ -CN →
(b) (CH3)2CHCH2I + Na+ N3- →
(c) (CH3)3CBr + HSCH2CH3 →
(d) (CH3)2CHOSO2CH3 + HOCH(CH3)2 →