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Notes Chemistry

Alkenes undergo electrophilic addition reactions where a proton (electrophile) adds to one sp2 carbon, forming a carbocation that then reacts with a nucleophile. The stability of the carbocation influences the major product, following Markovnikov's rule, which states that H+ adds to the sp2 carbon with the most hydrogens. Additionally, carbocations can rearrange to form more stable intermediates, and the Sn1 and Sn2 mechanisms describe different reaction pathways for nucleophilic substitutions.

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2 views5 pages

Notes Chemistry

Alkenes undergo electrophilic addition reactions where a proton (electrophile) adds to one sp2 carbon, forming a carbocation that then reacts with a nucleophile. The stability of the carbocation influences the major product, following Markovnikov's rule, which states that H+ adds to the sp2 carbon with the most hydrogens. Additionally, carbocations can rearrange to form more stable intermediates, and the Sn1 and Sn2 mechanisms describe different reaction pathways for nucleophilic substitutions.

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voon sj
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Reaction of alkene

The π bond of a double bond is weak, so it is easily broken. This allows alkenes to undergo addition
reactions. Because an alkene is a nucleophile, the first species it reacts with is an electrophile. Therefore,
we can more precisely say that alkenes undergo electrophilic addition reactions (Section 5.5). When an
alkene undergoes an electrophilic addition reaction with HBr, the first step is a relatively slow addition
of a proton (an electrophile) to the alkene (a nucleophile). A carbocation intermediate (an electrophile)
is formed, which then reacts rapidly with a bromide ion (a nucleophile) to form an alkyl halide. Notice
that each step involves the reaction of an electrophile with a nucleophile. The overall reaction is the
addition of an electrophile to one of the sp2 carbons of the alkene and the addition of a nucleophile to
the other sp2 carbon.

The relatively loosely held π electrons of the carbon–carbon double bond are attracted to an
electrophile.

■ Each reaction starts with the addition of an electrophile to one of the sp2 carbons of the alkene.

■ Each reaction concludes with the addition of a nucleophile to the other sp2 carbon.

The end result is that the p bond breaks and the electrophile and nucleophile form new σ bonds with
the sp2 carbons. Notice that the sp2 carbons in the reactant become sp3 carbons in the product.

The addition of hydrogen halide to an alkene


CARBOCATION STABILITY DEPENDS ON THE NUMBER OF ALKYL GROUPS ATTACHED TO THE
POSITIVELY CHARGED CARBON - The more alkyl groups attached to the positively charged carbon, the
more stable the carbocation.

ELECTROPHILIC ADDITION REACTIONS ARE REGIOSELECTIVE (major & minor)

Both of the following reactions form two products. In each case, the major product is the one obtained
from reaction of the nucleophile with the more stable carbocation—that is, the carbocation that is
formed more rapidly.

Tertiary carbocation is more stable, thus major product.


The Rule That Determines the Product of an Electrophilic Addition Reaction- the major product
obtained when a hydrogenhalide adds to an alkene results from adding the H+ to the sp2 carbon
bonded to the most hydrogens. Consequently, this is often referred to as Markovnikov’s rule. However,
Markovnikov’s rule is valid only for addition reactions in which the electrophile is H+.

THE ADDITION OF WATER TO AN ALKENE

MECHANISM FOR THE ACID-CATALYZED ADDITION OF WATER TO AN ALKENE

■ H+ (an electrophile) adds to the sp2 carbon of the alkene (a nucleophile) that is bonded to the most
hydrogens.

■ H2O (a nucleophile) adds to the carbocation (an electrophile), forming a protonated alcohol.

■ The protonated alcohol loses a proton because the pH of the solution is greater than the pKa of the
protonated alcohol (Section 2.10). (We saw that protonated alcohols are very strong acids)

Thus, the overall reaction is the addition of an electrophile to the sp2 carbon bonded to the most
hydrogens and addition of a nucleophile to the other sp2 carbon.

A CARBOCATION WILL REARRANGE IF IT CAN FORM A MORE STABLE CARBOCATION

Carbocations rearrange only if they become more stable as a result of the rearrangement.

1,2-Hydride Shift 1,2-Methyl Shift


Sn1 Sn2

Sn1 is a unimolecular reaction Sn2 is a bimolecular reaction

It follows a 1st order kinetic mechanism. It follows the 2nd order Kinetic mechanism.

Sn1 involves two steps Sn2 is a single-step process

In Sn1, the rate of reaction depends on the In Sn2, the rate of reaction depends on the
concentration of the substrate. concentration of both the substrate and the
nucleophile.

In Sn1 as the leaving group leaves, the In Sn2, the reaction happens in a single
substrate forms a carbocation intermediate. transition state.

Optically active substrate becomes optically Sn2 involves inversion reaction.


inactive and half of the optically active
substrate becomes similar.

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