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Chemistry of SN1 Reactions

The document discusses mechanisms for nucleophilic substitution reactions. It focuses on the SN1 and SN2 mechanisms. The SN1 mechanism is a two-step process where the first step is the slow formation of a carbocation intermediate through ionization of the substrate. The second step is a fast attack of this carbocation by the nucleophile. The rate of an SN1 reaction depends only on the concentration of the substrate and is first order. Factors that stabilize the carbocation intermediate such as heteroatoms, polar solvents, weaker leaving groups and more substituted substrates favor the SN1 mechanism.

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Sunil Sharma
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163 views1 page

Chemistry of SN1 Reactions

The document discusses mechanisms for nucleophilic substitution reactions. It focuses on the SN1 and SN2 mechanisms. The SN1 mechanism is a two-step process where the first step is the slow formation of a carbocation intermediate through ionization of the substrate. The second step is a fast attack of this carbocation by the nucleophile. The rate of an SN1 reaction depends only on the concentration of the substrate and is first order. Factors that stabilize the carbocation intermediate such as heteroatoms, polar solvents, weaker leaving groups and more substituted substrates favor the SN1 mechanism.

Uploaded by

Sunil Sharma
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Haloalkanes and haloarenes

If a substitution reaction is brought about by a nucleophile then it is known as nucleophilic substitution


reaction. A general
nucleophilic substitution reaction may be represented as:
R–L +N
Q
u R–Nu + L
Q
where L is a leaving group and N
Q
u is an incoming nucleophile.
In nucleophilic substitution two changes occur:
(i) breaking of the bond with leaving group
(ii) formation of bond with nucleophile
The principal mechanistic variations are associated with changes in the timing of the two processes.
Depending on nucleophiles, substrates, leaving groups and reaction conditions, several mechanisms are
possible but the
most common are SN1 and SN2 mechanisms.
SN1 Mechanism or SN1 Reaction
Main characteristics:
(1) The SN1 mechanism is mostly two-step process.
(2) The first step is a slow ionisation to form carbocation and thus rearrangement into stable carbocation
accompanied
frequently.
(3) The second step is a fast attack on the carbocation by the nucleophile. The carbocation being a very strong
electrophile reacts very fast with both strong and weak nucleophiles.
(5) Kinetics
The SN1 reaction is first order reaction which follows the rate law given below:
Rate = K [Substrate]
So that nucleophile plays no role in the mechanism.
(6) Effect of substrate structure:
The more stable the carbocation intermediate, the faster the SN1 mechanism.
The following is the decreasing order of reactivity of some substrates in SN1 reaction:
Ar3CX > Ar2CHX > R3CX > ArCH2X > CH2 = CH–CH2–X > R2CHX > RCH2X
(a) SN1 reactions are highly favoured if there is a heteroatom at the a-carbon because it highly stabilises the
carbocation
formed.
(b) Substrate containing carbonyl group on b-carbon does not gives SN1 reaction because carbonyl group has
very
strong–I effect which destabilises the carbocation reaction intermediate.
(c) The greater the crowding around the carbon having leaving group, the greater is the possibility of SN1
reaction.
For some tertiary substrates the rate of SN1 reactions is greatly increased if the b-carbon is highly substituted.
(7) E ffects of solvent: Polar solvents accelerate the SN1 reaction because it favours the formation of polar
transition
state.
(8) E ffect of leaving group: Weaker bases are good leaving groups and thus favour SN1 mechanism. Thus
the reactivity
order among the halide ions is:
I− > Br− > Cl− > F−
(9) E ffect of attacking nucleophile: Since the rate determining step of SN1 reaction does not involve the
incoming

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