The stereochemistry of E1 and E1CB is relatively
easily to dissect. In terms of the first step the regiochemistry
is reasonably clear (and there should be no stereochemistry
to consider) - in E1CB the most acidic proton (adjacent
to the leaving group) is taken and in E1 the leaving group leaves!
From the charged intermediate there are two possible olefinic
outcomes and the more stable of these will predominate - usually
the most stable one, with least steric crowding (trans >
cis). This is exemplified for E1 below;

Unfortunately, the stereochemistry of E2 is more complicated
because of the concerted nature of the mechanism.
For most favourable E2, the developing
p orbitals on the carbon atoms should be in the same
plane as the departing H+ and X-.
This is because the sigma orbital of the C-H bond must feed
into the antibonding sigma orbital of the C-X bond, and this
is best achieved if they are coplanar. This limits the E2 TS
to one of two conformations - anti-periplanar and syn-periplanar,
as shown below;
For the following reasons, anti- rather than syn-periplanar
elimination is preferred;
1. It allows the greatest separation of the base and the leaving
group in the TS.
2. The electrons from the sigma bonding C-H orbital can most
easily reach the rear lobe of the C-X sigma antibonding orbital
(cf SN2 where backside attack is favoured for the
same reason).
3. It is the most energetically favourable conformer with little
torsional strain/ steric crowding.
This has important stereochemical implications if the carbon
centres are chiral - syn- and anti- elimination would give different
alkene products, and the anti- one should be the major product.
There are some exceptions where syn-periplanar elimination
gives the major product - these usually occur when there is
some sort of neighbouring group effect, as is shown in the example
below;

It is also worth noting that in a cyclic compound undergoing
E2, there will not necessarily be a choice between eliminating
anti-periplanar or syn-periplanar - if the latter is forced,
it will often occur more slowly than it would have done had
it been able to anti-eliminate. Also, in cyclohexanes particularly,
the most stable conformer may be the one where no trans-diaxial
(another way of saying anti-periplanar when referring to cyclic
systems) eliminations are possible - in this case (an example
is shown below), if the ring cannot achieve a different conformation
where trans-diaxial positioning of HX is possible, the rate
will be appreciably slower.
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