Give the major organic 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 $C{H}_{3}OH)?$ Be sure to scroll down to see parts a through $e.$

a$.$ Draw the major organic product of

$C{H}_{3}C{H}_{2}C{H}_{2}Br+N{a}^{+-}CN$

c$.$ Draw the major organic product of

$(C{H}_3{)}_{3}CBr+HSC{H}_{2}C{H}_3$

e$.$ Which reactions will proceed faster in a polar, aprotic solvent?

$(C{H}_3{)}_{2}CHOS{O}_{2}C{H}_3+$HOCH$(C{H}_3{)}_2$

$C{H}_{3}C{H}_{2}C{H}_{2}Br+N{a}^{+-}CN$

$(C{H}_3{)}_{2}CHC{H}_{2}I+N{a}^{+-}{N}_3$

$(C{H}_3{)}_{3}CBr+HSC{H}_{2}C{H}_3$

b$.$ Draw the major organic product of

$(C{H}_3{)}_{2}CHC{H}_{2}I+N{a}^{+-}{N}_3$

d$.$ Draw the major organic product of

$(C{H}_3{)}_{2}CHOS{O}_{2}C{H}_3+$HOCH$(C{H}_3{)}_2$