Nucleophilic Substitution Reaction - Nur Aisyah Imran

Nama : Nur Aisyah Imran
Nim : 1913442009
1. What a is the benefid of learning SN1 and SN2
Answer :
As i know S is Substitution and N is Nucleophilik. In substitution nucleophilik there is 2

reaction is that SN1 and SN2, they describe a mechanism of organic reactivity, of chemical reactivity.
And they describe a bond-breaking process, and involves the replacement of one functional group or
atom with another negatively charged functional group or atom.
In the SN2, the nucleophile forms a bond to the substrate at the same time the leaving group leaves.
In the SN1, the leaving group leaves the substrate, and then the nucleophile forms a bond.
2. Write all factor that affect rate of SN1 and SN2
Answer :
Rate of SN2
The SN2 reaction is concerted. That is, the SN2 occurs in one step, and both the nucleophile
and substrate are involved in the rate determining step. Therefore the rate is dependent on both the
concentration of substrate and that of the nucleophile.
In the SN2 reaction, the big barrier is steric hindrance. Since the SN2 proceeds through a
backside attack, the reaction will only proceed if the empty orbital is accessible. The more groups
that are present around the vicinity of the leaving group, the slower the reaction will be. That’s why
the rate of reaction proceeds from primary (fastest) > secondary >> tertiary (slowest).
The SN2 tends to proceed with strong nucleophiles; by this, generally means negatively

charged nucleophiles such as CH3O(–), CN(–), RS(–), N3(–), HO(–), and others.
Since the SN2 proceeds through a backside attack, if a stereocenter is present the S N2 reaction
will give inversion of stereochemistry.
To design an effective SN2 reaction using alkyl halides, we need:
Uninhibited alkyl halides (preferably methyl or primary, but may be secondary)
Good exit group (preferably I or Br)
Strong nucleophile
Suitable solvents - the most effective poles
Rate of SN1
The SN1 reaction proceeds stepwise. The leaving group first leaves, whereupon a carbocation
forms that is attacked by the nucleophile.
In the SN1 reaction, the big barrier is carbocation stability. Since the first step of the SN1
reaction is loss of a leaving group to give a carbocation, the rate of the reaction will be proportional
to the stability of the carbocation. Carbocation stability increases with increasing substitution of the
carbon (tertiary > secondary >> primary) as well as with resonance.
For the SN1, since carbocation stability increases as we go from primary to secondary to
tertiary, the rate of reaction for the SN1 goes from primary (slowest) << secondary < tertiary (fastest)
The SN1 reaction tends to proceed in polar protic solvents such as water, alcohols, and
carboxylic acids, which stabilize the resulting (charged) carbocation that results from loss of the
leaving group. These also tend to be the nucleophiles for these reactions as well. If the S N1 leads to
the formation of a stereocenter, there will be a mixture of retention and inversion since the
nucleophile can attack from either face of the flat carbocation.
To design an effective S N 1 reaction using alkyl halides, we need:
Highly substituted (preferably substituted or resonance-stable, but secondary alkyl halides), ideally
which will not lead to rearrangements
Good exit group (preferably I or Br)
Non-alkaline nucleophiles (to reduce elimination side reactions)
Suitable solvents - most effective polar protics
3. distiguise caracteristic between SN1 and SN2
Answer :
Characteristics of SN1 and SN2 Reactions:
Mechanism:
SN1 Reactions: SN1 reactions have several steps; it starts with the removal of the leaving group,
resulting a carbocation and then the attack by the nucleophile.
SN2 Reactions: SN2 reactions are single step reactions where both nucleophile and substrate are
involved in the rate determining step. Therefore, the concentration of the substrate and that of the
nucleophile will affect to the rate determining step.
Barriers of the reaction:
SN1 Reactions: The first step of SN1 reactions is removing the leaving group to give a carbocation.
The rate of the reaction is proportional to the stability of the carbocation. Therefore, the formation of
the carbocation is the greatest barrier in SN1 reactions. The stability of the carbocation increases with
the number of substituents and the resonance. Tertiary carbocations are the most stable and primary
carbocations are the least stable (tertiary > secondary > primary).
SN2 Reactions: Steric hindrance is the barrier in SN2 reactions since it proceeds through a backside
attack. This happens only if the empty orbitals are accessible. When more groups are attached to the
leaving group, it slows the reaction. So the fastest reaction occurs in the formation of primary
carbocations whereas slowest is in tertiary carbocations (primary-fastest > secondary > tertiary
-slowest).
Nucleophile:
SN1 Reactions: SN1reactions require weak nucleophiles; they are neutral solvents such as CH3OH,
H2O, and CH3CH2OH.
SN2 Reactions: SN2 reactions require strong nucleophiles. In other words, they are negatively
charged nucleophiles such asCH3O–, CN–, RS–, N3– and HO–.
Solvent:
SN1 Reactions: SN1 reactions are favoured by polar protic solvents. Examples are water, alcohols,
and carboxylic acids. They can also act as the nucleophiles for the reaction.
SN2 Reactions: SN2 reactions proceed well in polar aprotic solvents such as acetone, DMSO, and
acetonitrile.
I find the Chart Comparing The SN1 vs SN2 Reaction

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Nama : Nur Aisyah Imran

1. What a is the benefid of learning SN1 and SN2

As i know S is Substitution and N is Nucleophilik. In substitution nucleophilik there is 2

2. Write all factor that affect rate of SN1 and SN2

The SN2 tends to proceed with strong nucleophiles; by this, generally means negatively

To design an effective SN2 reaction using alkyl halides, we need:

Uninhibited alkyl halides (preferably methyl or primary, but may be secondary)

Good exit group (preferably I or Br)

Suitable solvents - the most effective poles

To design an effective S N 1 reaction using alkyl halides, we need:

Good exit group (preferably I or Br)

Non-alkaline nucleophiles (to reduce elimination side reactions)

Suitable solvents - most effective polar protics

3. distiguise caracteristic between SN1 and SN2

Characteristics of SN1 and SN2 Reactions:

Barriers of the reaction:

I find the Chart Comparing The SN1 vs SN2 Reaction

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