Sn2 and Sn1 Reactions: Sethuranga Skanthan.P.T

SN2 AND SN1
REACTIONS
By:-
SETHURANGA SKANTHAN.P.T
SN1 REACTION
SN1 REACTION:-
• The SN1 reaction is a substitution reaction in organic chemistry, the name of which refers to the
Hughes-Ingold symbol of the mechanis.
• “SN” stands for “nucleophilic substitution”, and the “1” says that the rate-determining step is
unimolecular.
• Thus, the rate equation is often shown as having first-order dependence on electrophile and zero-
order dependence on nucleophile.
• Thus, the rate equation is often shown as having first-order dependence on electrophile and zero-
order dependence on nucleophile.
• This relationship holds for situations where the amount of nucleophile is much greater than that of
the intermediate.
• Instead, the rate equation may be more accurately described using steady-state kinetics.
• The reaction involves a carbocation intermediate and is commonly seen in reactions of secondary
or tertiary alkyl halides under strongly basic conditions or, under strongly acidic conditions, with
secondary or tertiary alcohols.
• With primary and secondary alkyl halides, the alternative SN2 reaction occurs. In inorganic chemistry, the
SN1 reaction is often known as the dissociative mechanism.
• This dissociation pathway is well-described by the cis effect.
• This reaction does not depend much on the strength of the nucleophile unlike the SN2 mechanism. This
type of mechanism involves two steps.
• The first step is the ionization of alkyl halide in the presence of aqueous acetone or ethyl alcohol. This step
provides a carbocation as an intermediate.
• In the first step of SN1 mechanism a carbonation is formed which is planer and hence attack of nucleophile
(second step) may occur from either side to give a racemic product but actually complete racemization
doesn’t take place.
• This is because the nucleophilic species attacks the carbonation even before the departing halides ion has
moved sufficiently away from the carbonation.
• The negatively charged halide ion shields the carbonation from being attacked on the front side and backside
attack which leads to inversion of configuration is preferred.
• Thus the actual product no doubt, consist of a mixture of enantiomers but the enantiomers with inverted
configuration would predominate and a complete racemization does not occurs.
An example of a reaction taking place with an SN1 reaction mechanism is
the hydrolysis of tert-butyl bromide forming tert-butanol:
SN2 REACTION
SN2 REACTION :-
• The SN2 reaction is a type of reaction mechanism that is common in organic chemistry.
• In this mechanism, one bond is broken and one bond is formed synchronously, i.e., in one step.
• SN2 is a kind of nucleophilic substitution reaction mechanism, the name referring to the
Hughes-Ingold symbol of the mechanism.
• Since two reacting species are involved in the slow (rate-determining) step, this leads to the
term substitution nucleophilic (bi-molecular) or SN2; the other major kind is SN1.
• Many other more specialized mechanisms describe substitution reactions.
• The reaction type is so common that it has other names, e.g. “bimolecular nucleophilic
substitution”, or, among inorganic chemists, “associative substitution” or “interchange
mechanism”.
• The reaction most often occurs at an aliphatic sp3 carbon center with an electronegative, stable
leaving group attached to it (often denoted X), which is frequently a halide atom.
• The breaking of the C–X bond and the formation of the new bond (often denoted C–Y or C–Nu)
occur simultaneously through a transition state in which a carbon under nucleophilic attack is
pentacoordinate, and approximately sp2 hybridised.
• The nucleophile attacks the carbon at 180° to the leaving group, since this provides the best
overlap between the nucleophile’s lone pair and the C–X σ* antibonding orbital.
• The leaving group is then pushed off the opposite side and the product is formed with inversion of
the tetrahedral geometry at the central atom.
• If the substrate under nucleophilic attack is chiral, then this often leads to inversion of
configuration (stereochemistry), called a Walden inversion.
Example of the SN2 reaction, the attack of Br− (the nucleophile) on an ethyl
chloride (the electrophile) results in ethyl bromide, with chloride ejected as the
leaving group.

Sn2 and Sn1 Reactions: Sethuranga Skanthan.P.T

Uploaded by

Copyright:

Available Formats

Sn2 and Sn1 Reactions: Sethuranga Skanthan.P.T

Uploaded by

Document Information

Original Description:

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Sn2 and Sn1 Reactions: Sethuranga Skanthan.P.T

Uploaded by

Copyright:

Available Formats

SN2 AND SN1

You might also like