E1 reaction, also known as Elimination-Unimolecular reaction, is a type of chemical reaction that involves the removal of a leaving group and a proton from adjacent carbon atoms in a molecule, resulting in the formation of a double bond.
The reaction mechanism involves a two-step process: in the
first step, a leaving group departs from the molecule, generating a carbocation
intermediate. In the second step, a proton is removed from an adjacent carbon
atom, resulting in the formation of a double bond and the regeneration of a
protonated leaving group.
E1 reactions typically occur in the presence of a strong
base or heat, and they are most commonly observed in reactions involving
secondary or tertiary alkyl halides. The rate of an E1 reaction depends only on
the concentration of the substrate, as the reaction involves the formation of a
carbocation intermediate that can be stabilized by neighboring groups.
Zaitsev and Hoffman products refer to two possible products
that can be formed during an elimination reaction, particularly when a base is
used to remove a proton from a beta-carbon atom in a molecule.
The Zaitsev product is the more stable and predominant
product, which is formed when the elimination reaction occurs through the
transition state that leads to the most substituted alkene. This product is
also known as the "Saytzeff" product.
On the other hand, the Hoffman product is the less stable
and less substituted product, which is formed when the elimination reaction
occurs through the transition state that leads to the least substituted alkene.
This product is also known as the "anti-Zaitsev" product.
The preference for the formation of Zaitsev or Hoffman
products depends on the reaction conditions, the nature of the substrate, and
the strength of the base used. Generally, Zaitsev products are favored in
reactions involving strong bases and substrates that can stabilize the negative
charge of the alkene intermediate through resonance or inductive effects.
Meanwhile, Hoffman products are favored in reactions involving weaker bases or
substrates that cannot stabilize the negative charge of the alkene
intermediate.
It is important to note that while Zaitsev products are
generally more stable and predominant, there are some instances where Hoffman
products may be preferred, such as when steric hindrance around the beta-carbon
atom makes it difficult for the base to approach and remove the proton from
that position.
ANSWER (a)
Dehydration of Tertiary Alcohol
The dehydration of tertiary alcohols follows the E1
mechanism (elimination unimolecular), which involves the formation of a carbocation
intermediate.
In the first step of the reaction, a proton from the
beta-carbon adjacent to the hydroxyl group is removed by a strong acid, such as
sulfuric acid (H2SO4) or phosphoric acid (H3PO4),
resulting in the formation of a carbocation intermediate. Tertiary carbocations
are relatively stable due to the presence of three alkyl groups that can
stabilize the positive charge of the carbocation.
In the second step, a water molecule acts as a base and
removes a proton from the beta-carbon, leading to the formation of a double
bond and the release of a protonated water molecule (H3O+). The resulting
product is an alkene, which is typically the major product of the reaction.
The (c) is the major product, (b) and (d) are the minor
product. The (a) is not the product because the proton that has been remove is
not in beta position. Furthermore, the hydride shift do not occur because its
already tertiary carbocation.
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