H
Br
Br
H
H
H
t-Bu
t-Bu
H
H
H
H
trans
cis
The atoms shown in red cannot fulfill
The atoms shown in red fulfill the
the anticoplanar requirement.
anticoplanar requirement for E2.
Elimination is slower or not possible
Elimination is possible and fast.
5)
H
C
3
6) The small, unhindered base ethoxide yields the more stable alkene (Saytzeff’s product, i.e.
the more highly substituted alkene). When the bulky t-butoxide base is used, the most accessible
hydrogen is removed. This results in the least highly substituted alkene (Hoffman’s product).
CH
3
I
CH
CH
CH
O
3
3
2
Saytzeff's product
CH
3
CH
2
H
C
O
3
CH
3
Hoffman's product
7) III, IV, and V.
8) In elimination reactions, the most highly substituted alkene predominates.
9)
H
CH
3
H
C
CH
3
3