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Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

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Table of contents
Nucleophilic substitution reaction
Bimolecular nucleophilic substitution reaction (SN2) 
Unimolecular Nucleophilic Substitution Reaction (SN1) 
Comparison of SN1 and SN2 reactions :
SN1 (Nucleophilic substitution intramolecular )
SNNGP(Neighbouring group participation)
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The reactions of haloalkanes may be divided into the following categories:

1. Nucleophilic substitution

2. Elimination reactions

3. Reaction with metals.

Nucleophilic substitution reaction

Chemical reactions of alkyl halide: 

Those organic compounds in which an sp3 hybridized carbon is bonded to an electronegative atom or group can undergo two types of reaction e.g. substitution reactions in which the electronegative atom or group is replaced by another atom or group. The second is the elimination reaction in which the electronegative atom or group is eliminated along with hydrogen from an adjacent carbon. The electronegative atom or group which is substituted or eliminated is known as leaving group. Nucleophilic Substitution ReactionNucleophilic Substitution Reaction


Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Because of more electronegativity of the halogen atom, it has a partial negative charge and partial positive cha develops on the carbon atom.

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

X = F, Cl, Br, I

Due to this polar carbon - halogen bond alkyl halides shows nucleophilic substitution and elimination reaction.

There are two important mechanisms for the substitution reaction:

  1. A nucleophile is attracted to the partially positively charged carbon. As the nucleophile approaches the carbon, it causes the carbon - halogen bond to break heterolytically (the halogen keeps both of the bonding electrons.)
    Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  2. The carbon-halogen bond breaks heterolytically without any assistance from the nucleophile, with the help of polar protic solvent and carbocation is formed (solvolysis). Formed carbocation then reacts with the nucleophile to form the substitution product.

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE


Bimolecular nucleophilic substitution reaction (SN2) 

The mechanism of SN2 reaction

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

                                        transition state

Characteristic of SN2

  1. It is bimolecular, unistep process
  2. It is the second-order reaction because in the Rds two species are involved
  3. Kinetics of the reaction → rate ∝ [alkyl halide] [nucleophile]
    rate =  k[alkyl halide] [nucleophile]
    If the concentration of alkyl halide in the reaction mixture is doubled, the rate of the nucleophilic substitution reaction is double. If the concentration of nucleophile is doubled the rate of reaction is also double. If the concentration of both is doubled then the rate of the reaction quadruples.
  4. Energetics of the reaction:
    Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
    Figure: A free energy diagrams for a hypothetical SN2 reaction that takes place with a negative DGº
  5. No intermediates are formed in the SN2 reaction, the reaction proceeds through the formation of an unstable arrangement of atoms or group called transition state.
  6. Stereochemistry of SN2 reaction: As we saw earlier, in an SN2 mechanism the nucleophile attacks from the backside, that is from the side directly opposite to the leaving group. this mode of attack causes an inversion of configuration at the carbon atom that is the target of nucleophilic attack. This inversion is also known as Walden inversion.

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE


Factors affecting the rate of an SN2 reaction

A number of factors affect the relative rate of SN2 reaction, the most important factors are:

  1. Structure of the substrate
  2. Concentration and reactivity of the nucleophile
  3. Effect of the solvent
  4. Nature of the leaving group

1. Effect of the structure of the substrate:

Order of reactivity in SN2 reaction : - CH> 1º > 2º >> 3º (unreactive)

the important factor behind this order of reactivity is a steric effect. Very large and bulky groups can often hinder the formation of the required transition state and crowding raises the energy of the transition state and slows down the reaction.

Relative rates of reactions of an alkyl halide in SN2  reaction

Substituent

Compound

Relative rate

Methyl

CH3X

30

CH3CH2X

1

(CH3)2CHX

0.02

Neopentyl

(CH3)3CCH2X

0.00001

(CH3)3CX

~0


2. Concentration and reactivity of the nucleophile

According to the kinetics of SN2 increasing the concentration of the nucleophile increases the rate of an SN2 reaction. The nature of nucleophile strongly affects the rate of an SN2 reaction. A stronger nucleophile is much more effective than a weaker one. For example, we know that a negatively charged nucleophile is more reactive than its conjugate acid e.g. HO- > H2O, RO- > ROH.

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE


Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

                                            Steric effects on nucleophilicity


3. The effect of the solvent: In polar protic solvent large nucleophiles are good, and the halide ions show the following order: I- > Br- > Cl- > F- (in polar protic solvent)

This effect is related to the strength of the interaction between nucleophile and solvent molecules of polar protic solvent forms a hydrogen bond to nucleophiles in the following manner. Because small nucleophile is solvated more by the polar protic solvent thus its nucleophilicity decreases and the rate of SN2 decreases

Relative nucleophilicity in a polar protic solvent:
SH+ > CN- > I- > OH-  > N3- > Br- > ACO- > Cl- > F- > H2O

So, polar protic solvents are not useful for the rate of SN2, if the nucleophile is anionic. But polar aprotic solvent does not have any active hydrogen atom so they can not forms an H bond with nucleophiles. Polar aprotic solvent has a crowded positive centre, so they do not solvate the anion appreciably therefore the rate of SN2 reactions increased when they are carried out in a polar aprotic solvent.

Examples of a polar aprotic solvent.

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

In DMSO, the relative order of reactivity of halide ions is: F- > Cl- > Br- > I-

4. The nature of the leaving group: The best-leaving groups are those that become the most stable ion after they leave because leaving group generally leave as a negative ion, so those leaving groups are good, which stabilise negative charge most effectively and weak base do this best, so weaker bases are good leaving groups. A good leaving group always stabilize the transition state and lowers its free energy of activation and thereby increases the rate of the reaction.

Order of leaving ability of halide ion: I- > Br- > Cl- > F- 

Other leaving groups are Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Strongly basic ions rarely act as leaving group:

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Examples of SN2 reactions of alkyl halide → 

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Nucleophile  Product Class of Product
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEAlkyl halide
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEAlcohol
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEEther
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEThiol(mercaptan)
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEThioether (sulphide)
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEAmine
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEAzide
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEAlkyne
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEENitrile
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEER - COO - R  Ester
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE[R - PPh3]+ Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Posphonium salt

Question 1: Complete the following reactions with mechanism

(a) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE 

Sol. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

 

(b) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE ?

Sol.Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE (p-Nitroanisole)

 

(c)Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Ph - CH2Cl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Sol. CH3-CH2-O! is present in excess and it is stronger nucleophile than Ph - O! so the product is Ph-CH2 - OEt

(d) CH3 - C ≡ CH Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE X Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Y

Sol.Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

(e) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Ph3 → Salt

Sol. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Question 2: When the concentration of alkyl halide is tripled and the concentration of OH- ion is reduced to half, the rate of SNreaction increases by : 

(A) 3 times (B) 2 times (C) 1.5 times (D) 6 times 

Ans: c

 

Unimolecular Nucleophilic Substitution Reaction (SN1) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Characteristics of SN1 reactions 

  1. It is a unimolecular, two-step process and intermediate is formed, (intermediate is carbocation)
  2. It is a first-order reaction
  3. Kinetics of the reaction, Rate ∝ [Alkyl halide]
    Rate = k[(CH3)3C-X]
    The rate of SN1 reaction is independent of the concentration and reactivity of nucleophile.
  4. Stereochemistry of SN1 reaction:
    In the SN1 mechanism, the carbocation intermediate is sp2 hybridized and planar. A nucleophile can attack the carbocation from either face if the reactant is chiral than after the attack of nucleophile from both faces gives both enantiomers of the product, which is called recemization.

    Mechanism of recemization (SN1):

    Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
    Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

  5. Energetics of the SN1
    Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
    Figure: free energy diagram for the SN1 reaction.

Factors affecting the rates of SN1 

  1. The structure of the substrate:
    The Rds of the SN1 reaction is an ionization step, in this step form a carbocation. This ionisation is a strongly endothermic process, rate of SN1 reaction depends strongly on carbocation stability because carbocation is the intermediate of SN1 reaction which determines the energy of activation of the reaction.
    SN1 reactivity : 3º > 2º > 1º > CH3 - X
  2. Concentration and reactivity of the nucleophile:
    The rate of SN1 reactions are unaffected by the concentration and nature of the nucleophile
  3. Effect of the solvent:
    Because to solvate cations and anions so effectively the use of polar protic solvent will greatly increase the rate of ionization of an alkyl halide in any SN1 reaction. It does this because solvation stabilizes the transition state leading to the intermediate carbocation and halide ion more than it does the reactant, thus the energy of activation is lower.
    Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  4. The nature of the leaving group:
    In the SN1 reaction, the leaving group begins to acquire a negative charge as the transition state is reached the stabilisation of this developing negative charge at the leaving group stabilizes the transition state and: this lowers the free energy of activation and thereby increases the rate of reaction.

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

 

Comparison of SN1 and SN2 reactions :

 

 

SN1

SN2

(i)

Effect of the nucleophile

Nucleophile strength is not important

A stronger nucleophile is required

(ii)

Effect of the substrate

3° > 2° > 1° > CH3X

CH3X > 1° >2°

(iii)

Effect of solvent

Good ionizing solvent required

It goes faster in a less polar solvent if Nud is present

(iv)

Kinetics

Rate = k [R-X]

Rate = k[R-X] [Nu°]

(v)

Stereochemistry

Racemisation

Walden inversion

(vi)

Rearrangement

common

Impossible

 

Question 3:  Predict the compound in each pair that will undergo solvolysis (in aqueous ethanol) more rapidly.

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Sol. (a) II > I (b) II > I (c) I > II (d) II > I (e) II > I

Question 4: Give the solvolysis products expected when each compound is heated in ethanol

(a) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE 
(b) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE 
(c) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE 
(d) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Sol. (a) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE 
(b) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE 
(c) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE 
(d) Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

 

Question 5: The rate of SN1 reaction is fastest with

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Ans. (A)

The reaction of RX with aq. KOH

  1.  Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE R - OH + KCl
  2. CH3-CH2-Cl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE CH3-CH2-OH
  3. CH3-CH Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE CH3-CH Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE CH3-CHO
  4. CH3-CChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEEChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE CH3-CChemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE CH3COOH
  5. C - C - C - C - Br Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE C - C - C - C - OH
  6. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  7. 14C = C - C - I Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE 14C = C - C - OH + C = C - C14 - OH
  8. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Other Nucleophilic reaction of R - X :-Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

WillionSon's Ether Synthesis: (SN2)

  1. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  2. EtONa + Me - Cl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE EtOMe
  3. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE EtOMe
    Rate (2) > (3) 2 is better method. (Due to less steric hindrence)
  4. MeONa + PhCl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE No reaction
  5. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE + NaCl
  6. Me3CO!NaÅ + MeCl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Me3COMe + NaCl
  7. MeO!NaÅ + Me3C - Cl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE + MeOH + NaCl
  8. PhONa + Me3C-Cl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE + PhOH + NaCl
  9. Me3CONa + Ph-Cl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE No. reaction
    Me3CO-Ph can not be prepared by Williamson's ether synthesis.
  10.  Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  11. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  12.  Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE + HCl
  13. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE + HBr
  14.  Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE (Pyridinium salt)

Hydrolysis of Ether

  1. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  2. MeOEt Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Et - Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE + Me - OH
  3. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  4. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  5. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Reaction of ether with HI :

  1.  Me - O - Et Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  2. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE (Due to formation of more stable carbocation)

With moist and dry Ag2O :

  1. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  2. 2Me - Cl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Me - O - Me + 2AgCl
  3. Me - Cl + EtCl Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE Me - O - Et + Me - O - Me + EtOEt

SN1 (Nucleophilic substitution intramolecular )

Darzon's process

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

Mechanism:

Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE

R - Cl + O = S = O ­ (g)

Note : (1) In SNi retention of the configuration takes place.

Note : (2) In presence of pyridine above reaction follow the SN2 reaction mechanism.

SNNGP(Neighbouring group participation)

An increase in the rate of SN reaction due to attack of internal nucleophile is called SNNGP is also known as Anchimeric assistance.

For SNNGP

  1. Internal nucleophile must be present
  2. Internal nucleophile must be anti to lg.

During NGP:

  1. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
  2. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE (enantiomers)
  3. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE + (enantiomer) Rate 3 > 2 > 1
  4. Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE
The document Chemical Reaction: Nucleophilic Substitution Reactions Notes | Study Chemistry for JEE - JEE is a part of the JEE Course Chemistry for JEE.
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