The following are predicted to take place via either $S_{N}1,S_{N}2,E1,$ or $E2$ mechanisms, or$,$ alternatively, no

reaction. Some reactions may start with an initial proton transfer. $($a$)$ Give the major product $($if any$),($b$)$

determine reaction type$($s$),$ and $($c$)$ briefly explain why a particular mechanism. Although you are not asked to

show the mechanism, you should draw out the mechanism on scratch paper. Knowing the mechanism will help

you be aware of carbocation formation and rearrangements. Show stereochemistry when appropriate.

NaH

a$)TsCl,$ py

b$)$ NaCN

E

a$)PB{r}_3$

$b$

$H_{3}P{O}_4,$

NaI

$HBr$

r

$H_{2}O,H_{2}S{O}_4($acid workup$)$

NaH

$2$

NaH