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1 | 5405-5408 | 7
6 7
6 7
Chemical
Chemical
Chemical
Chemical
Chemical
Reactions
Reactions
Reactions
Reactions
Reactions
Compound
Density (g/mL)
Compound
Density (g/mL)
n–C3H7Cl
0 89
CH2Cl2
1 |
1 | 5406-5409 | 7
6 7
Chemical
Chemical
Chemical
Chemical
Chemical
Reactions
Reactions
Reactions
Reactions
Reactions
Compound
Density (g/mL)
Compound
Density (g/mL)
n–C3H7Cl
0 89
CH2Cl2
1 336
n–C3H7Br
1 |
1 | 5407-5410 | 7
Chemical
Chemical
Chemical
Chemical
Chemical
Reactions
Reactions
Reactions
Reactions
Reactions
Compound
Density (g/mL)
Compound
Density (g/mL)
n–C3H7Cl
0 89
CH2Cl2
1 336
n–C3H7Br
1 335
CHCl3
1 |
1 | 5408-5411 | 89
CH2Cl2
1 336
n–C3H7Br
1 335
CHCl3
1 489
n-C3H7I
1 |
1 | 5409-5412 | 336
n–C3H7Br
1 335
CHCl3
1 489
n-C3H7I
1 747
CCl4
1 |
1 | 5410-5413 | 335
CHCl3
1 489
n-C3H7I
1 747
CCl4
1 595
6 |
1 | 5411-5414 | 489
n-C3H7I
1 747
CCl4
1 595
6 7 |
1 | 5412-5415 | 747
CCl4
1 595
6 7 1
Reactions of
Haloalkanes
Rationalised 2023-24
170
Chemistry
already existing nucleophile in a molecule is called nucleophilic
substitution reaction |
1 | 5413-5416 | 595
6 7 1
Reactions of
Haloalkanes
Rationalised 2023-24
170
Chemistry
already existing nucleophile in a molecule is called nucleophilic
substitution reaction Haloalkanes are substrate in these reactions |
1 | 5414-5417 | 7 1
Reactions of
Haloalkanes
Rationalised 2023-24
170
Chemistry
already existing nucleophile in a molecule is called nucleophilic
substitution reaction Haloalkanes are substrate in these reactions In this type of reaction, a nucleophile reacts with haloalkane (the
substrate) having a partial positive charge on the carbon atom bonded
to halogen |
1 | 5415-5418 | 1
Reactions of
Haloalkanes
Rationalised 2023-24
170
Chemistry
already existing nucleophile in a molecule is called nucleophilic
substitution reaction Haloalkanes are substrate in these reactions In this type of reaction, a nucleophile reacts with haloalkane (the
substrate) having a partial positive charge on the carbon atom bonded
to halogen A substitution reaction takes place and halogen atom,
called leaving group departs as halide ion |
1 | 5416-5419 | Haloalkanes are substrate in these reactions In this type of reaction, a nucleophile reacts with haloalkane (the
substrate) having a partial positive charge on the carbon atom bonded
to halogen A substitution reaction takes place and halogen atom,
called leaving group departs as halide ion Since the substitution
reaction is initiated by a nucleophile, it is called nucleophilic
substitution reaction |
1 | 5417-5420 | In this type of reaction, a nucleophile reacts with haloalkane (the
substrate) having a partial positive charge on the carbon atom bonded
to halogen A substitution reaction takes place and halogen atom,
called leaving group departs as halide ion Since the substitution
reaction is initiated by a nucleophile, it is called nucleophilic
substitution reaction It is one of the most useful classes of organic reactions of alkyl
halides in which halogen is bonded to sp3 hybridised carbon |
1 | 5418-5421 | A substitution reaction takes place and halogen atom,
called leaving group departs as halide ion Since the substitution
reaction is initiated by a nucleophile, it is called nucleophilic
substitution reaction It is one of the most useful classes of organic reactions of alkyl
halides in which halogen is bonded to sp3 hybridised carbon The
products formed by the reaction of haloalkanes with some common
nucleophiles are given in Table 6 |
1 | 5419-5422 | Since the substitution
reaction is initiated by a nucleophile, it is called nucleophilic
substitution reaction It is one of the most useful classes of organic reactions of alkyl
halides in which halogen is bonded to sp3 hybridised carbon The
products formed by the reaction of haloalkanes with some common
nucleophiles are given in Table 6 4 |
1 | 5420-5423 | It is one of the most useful classes of organic reactions of alkyl
halides in which halogen is bonded to sp3 hybridised carbon The
products formed by the reaction of haloalkanes with some common
nucleophiles are given in Table 6 4 Groups like cyanides and nitrites possess two nucleophilic centres
and are called ambident nucleophiles |
1 | 5421-5424 | The
products formed by the reaction of haloalkanes with some common
nucleophiles are given in Table 6 4 Groups like cyanides and nitrites possess two nucleophilic centres
and are called ambident nucleophiles Actually cyanide group is a
hybrid of two contributing structures and therefore can act as a
nucleophile in two different ways [VCºN « :C=NV], i |
1 | 5422-5425 | 4 Groups like cyanides and nitrites possess two nucleophilic centres
and are called ambident nucleophiles Actually cyanide group is a
hybrid of two contributing structures and therefore can act as a
nucleophile in two different ways [VCºN « :C=NV], i e |
1 | 5423-5426 | Groups like cyanides and nitrites possess two nucleophilic centres
and are called ambident nucleophiles Actually cyanide group is a
hybrid of two contributing structures and therefore can act as a
nucleophile in two different ways [VCºN « :C=NV], i e , linking through
Table 6 |
1 | 5424-5427 | Actually cyanide group is a
hybrid of two contributing structures and therefore can act as a
nucleophile in two different ways [VCºN « :C=NV], i e , linking through
Table 6 4: Nucleophilic Substitution of Alkyl Halides (R–X)
Reagent
Nucleophile
Substitution
Class of main
(Nu–)
product R–Nu
product
NaOH (KOH)
HO–
ROH
Alcohol
H2O
H2O
ROH
Alcohol
NaOR¢
R¢O–
ROR¢
Ether
NaI
I–
R—I
Alkyl iodide
NH3
NH3
RNH2
Primary amine
R¢NH2
R¢NH2
RNHR¢
Sec |
1 | 5425-5428 | e , linking through
Table 6 4: Nucleophilic Substitution of Alkyl Halides (R–X)
Reagent
Nucleophile
Substitution
Class of main
(Nu–)
product R–Nu
product
NaOH (KOH)
HO–
ROH
Alcohol
H2O
H2O
ROH
Alcohol
NaOR¢
R¢O–
ROR¢
Ether
NaI
I–
R—I
Alkyl iodide
NH3
NH3
RNH2
Primary amine
R¢NH2
R¢NH2
RNHR¢
Sec amine
R¢R¢¢NH
R¢R¢¢NH
RNR¢R¢¢
Tert |
1 | 5426-5429 | , linking through
Table 6 4: Nucleophilic Substitution of Alkyl Halides (R–X)
Reagent
Nucleophile
Substitution
Class of main
(Nu–)
product R–Nu
product
NaOH (KOH)
HO–
ROH
Alcohol
H2O
H2O
ROH
Alcohol
NaOR¢
R¢O–
ROR¢
Ether
NaI
I–
R—I
Alkyl iodide
NH3
NH3
RNH2
Primary amine
R¢NH2
R¢NH2
RNHR¢
Sec amine
R¢R¢¢NH
R¢R¢¢NH
RNR¢R¢¢
Tert amine
KCN
RCN
Nitrile
(cyanide)
AgCN
Ag-CN:
RNC
Isonitrile
(isocyanide)
KNO2
O=N—O
R—O—N=O
Alkyl nitrite
AgNO2
Ag—Ö—N=O
R—NO2
Nitroalkane
R¢COOAg
R¢COO–
R¢COOR
Ester
LiAlH4
H
RH
Hydrocarbon
R¢– M+
R¢–
RR¢
Alkane
Rationalised 2023-24
171 Haloalkanes and Haloarenes
carbon atom resulting in alkyl cyanides and through nitrogen atom
leading to isocyanides |
1 | 5427-5430 | 4: Nucleophilic Substitution of Alkyl Halides (R–X)
Reagent
Nucleophile
Substitution
Class of main
(Nu–)
product R–Nu
product
NaOH (KOH)
HO–
ROH
Alcohol
H2O
H2O
ROH
Alcohol
NaOR¢
R¢O–
ROR¢
Ether
NaI
I–
R—I
Alkyl iodide
NH3
NH3
RNH2
Primary amine
R¢NH2
R¢NH2
RNHR¢
Sec amine
R¢R¢¢NH
R¢R¢¢NH
RNR¢R¢¢
Tert amine
KCN
RCN
Nitrile
(cyanide)
AgCN
Ag-CN:
RNC
Isonitrile
(isocyanide)
KNO2
O=N—O
R—O—N=O
Alkyl nitrite
AgNO2
Ag—Ö—N=O
R—NO2
Nitroalkane
R¢COOAg
R¢COO–
R¢COOR
Ester
LiAlH4
H
RH
Hydrocarbon
R¢– M+
R¢–
RR¢
Alkane
Rationalised 2023-24
171 Haloalkanes and Haloarenes
carbon atom resulting in alkyl cyanides and through nitrogen atom
leading to isocyanides Similarly nitrite ion also represents an ambident
nucleophile with two different points of linkage [–O— N
i i
=O] |
1 | 5428-5431 | amine
R¢R¢¢NH
R¢R¢¢NH
RNR¢R¢¢
Tert amine
KCN
RCN
Nitrile
(cyanide)
AgCN
Ag-CN:
RNC
Isonitrile
(isocyanide)
KNO2
O=N—O
R—O—N=O
Alkyl nitrite
AgNO2
Ag—Ö—N=O
R—NO2
Nitroalkane
R¢COOAg
R¢COO–
R¢COOR
Ester
LiAlH4
H
RH
Hydrocarbon
R¢– M+
R¢–
RR¢
Alkane
Rationalised 2023-24
171 Haloalkanes and Haloarenes
carbon atom resulting in alkyl cyanides and through nitrogen atom
leading to isocyanides Similarly nitrite ion also represents an ambident
nucleophile with two different points of linkage [–O— N
i i
=O] The linkage
through oxygen results in alkyl nitrites while through nitrogen atom, it
leads to nitroalkanes |
1 | 5429-5432 | amine
KCN
RCN
Nitrile
(cyanide)
AgCN
Ag-CN:
RNC
Isonitrile
(isocyanide)
KNO2
O=N—O
R—O—N=O
Alkyl nitrite
AgNO2
Ag—Ö—N=O
R—NO2
Nitroalkane
R¢COOAg
R¢COO–
R¢COOR
Ester
LiAlH4
H
RH
Hydrocarbon
R¢– M+
R¢–
RR¢
Alkane
Rationalised 2023-24
171 Haloalkanes and Haloarenes
carbon atom resulting in alkyl cyanides and through nitrogen atom
leading to isocyanides Similarly nitrite ion also represents an ambident
nucleophile with two different points of linkage [–O— N
i i
=O] The linkage
through oxygen results in alkyl nitrites while through nitrogen atom, it
leads to nitroalkanes Mechanism: This reaction has been found to proceed by two different
mechanims which are described below:
(a) Substitution nucleophilic bimolecular (SN2)
The reaction between CH3Cl and hydroxide ion to yield methanol and
chloride ion follows a second order kinetics, i |
1 | 5430-5433 | Similarly nitrite ion also represents an ambident
nucleophile with two different points of linkage [–O— N
i i
=O] The linkage
through oxygen results in alkyl nitrites while through nitrogen atom, it
leads to nitroalkanes Mechanism: This reaction has been found to proceed by two different
mechanims which are described below:
(a) Substitution nucleophilic bimolecular (SN2)
The reaction between CH3Cl and hydroxide ion to yield methanol and
chloride ion follows a second order kinetics, i e |
1 | 5431-5434 | The linkage
through oxygen results in alkyl nitrites while through nitrogen atom, it
leads to nitroalkanes Mechanism: This reaction has been found to proceed by two different
mechanims which are described below:
(a) Substitution nucleophilic bimolecular (SN2)
The reaction between CH3Cl and hydroxide ion to yield methanol and
chloride ion follows a second order kinetics, i e , the rate depends
upon the concentration of both the reactants |
1 | 5432-5435 | Mechanism: This reaction has been found to proceed by two different
mechanims which are described below:
(a) Substitution nucleophilic bimolecular (SN2)
The reaction between CH3Cl and hydroxide ion to yield methanol and
chloride ion follows a second order kinetics, i e , the rate depends
upon the concentration of both the reactants Haloalkanes react with KCN to form alkyl cyanides as main product
while AgCN forms isocyanides as the chief product |
1 | 5433-5436 | e , the rate depends
upon the concentration of both the reactants Haloalkanes react with KCN to form alkyl cyanides as main product
while AgCN forms isocyanides as the chief product Explain |
1 | 5434-5437 | , the rate depends
upon the concentration of both the reactants Haloalkanes react with KCN to form alkyl cyanides as main product
while AgCN forms isocyanides as the chief product Explain KCN is predominantly ionic and provides cyanide ions in solution |
1 | 5435-5438 | Haloalkanes react with KCN to form alkyl cyanides as main product
while AgCN forms isocyanides as the chief product Explain KCN is predominantly ionic and provides cyanide ions in solution Although both carbon and nitrogen atoms are in a position to donate
electron pairs, the attack takes place mainly through carbon atom and
not through nitrogen atom since C—C bond is more stable than C—N
bond |
1 | 5436-5439 | Explain KCN is predominantly ionic and provides cyanide ions in solution Although both carbon and nitrogen atoms are in a position to donate
electron pairs, the attack takes place mainly through carbon atom and
not through nitrogen atom since C—C bond is more stable than C—N
bond However, AgCN is mainly covalent in nature and nitrogen is free
to donate electron pair forming isocyanide as the main product |
1 | 5437-5440 | KCN is predominantly ionic and provides cyanide ions in solution Although both carbon and nitrogen atoms are in a position to donate
electron pairs, the attack takes place mainly through carbon atom and
not through nitrogen atom since C—C bond is more stable than C—N
bond However, AgCN is mainly covalent in nature and nitrogen is free
to donate electron pair forming isocyanide as the main product Example 6 |
1 | 5438-5441 | Although both carbon and nitrogen atoms are in a position to donate
electron pairs, the attack takes place mainly through carbon atom and
not through nitrogen atom since C—C bond is more stable than C—N
bond However, AgCN is mainly covalent in nature and nitrogen is free
to donate electron pair forming isocyanide as the main product Example 6 5
Example 6 |
1 | 5439-5442 | However, AgCN is mainly covalent in nature and nitrogen is free
to donate electron pair forming isocyanide as the main product Example 6 5
Example 6 5
Example 6 |
1 | 5440-5443 | Example 6 5
Example 6 5
Example 6 5
Example 6 |
1 | 5441-5444 | 5
Example 6 5
Example 6 5
Example 6 5
Example 6 |
1 | 5442-5445 | 5
Example 6 5
Example 6 5
Example 6 5
Solution
Solution
Solution
Solution
Solution
The above reaction can be represented diagrammatically as shown in
Fig |
1 | 5443-5446 | 5
Example 6 5
Example 6 5
Solution
Solution
Solution
Solution
Solution
The above reaction can be represented diagrammatically as shown in
Fig 6 |
1 | 5444-5447 | 5
Example 6 5
Solution
Solution
Solution
Solution
Solution
The above reaction can be represented diagrammatically as shown in
Fig 6 2 |
1 | 5445-5448 | 5
Solution
Solution
Solution
Solution
Solution
The above reaction can be represented diagrammatically as shown in
Fig 6 2 It depicts a bimolecular nucleophilic substitution (SN2) reaction;
the incoming nucleophile interacts with alkyl halide causing the
carbon-halide bond to break and a new bond is formed between
carbon and attacking nucleophile |
1 | 5446-5449 | 6 2 It depicts a bimolecular nucleophilic substitution (SN2) reaction;
the incoming nucleophile interacts with alkyl halide causing the
carbon-halide bond to break and a new bond is formed between
carbon and attacking nucleophile Here it is C-O bond formed between
C and -OH |
1 | 5447-5450 | 2 It depicts a bimolecular nucleophilic substitution (SN2) reaction;
the incoming nucleophile interacts with alkyl halide causing the
carbon-halide bond to break and a new bond is formed between
carbon and attacking nucleophile Here it is C-O bond formed between
C and -OH These two processes take place simultaneously in a
Fig |
1 | 5448-5451 | It depicts a bimolecular nucleophilic substitution (SN2) reaction;
the incoming nucleophile interacts with alkyl halide causing the
carbon-halide bond to break and a new bond is formed between
carbon and attacking nucleophile Here it is C-O bond formed between
C and -OH These two processes take place simultaneously in a
Fig 6 |
1 | 5449-5452 | Here it is C-O bond formed between
C and -OH These two processes take place simultaneously in a
Fig 6 2:
Red ball represents the incoming hydroxide ion and green ball represents
the outgoing halide ion
In the year 1937,
Edward Davies Hughes
and Sir Christopher
Ingold
proposed
mechanism for an SN2a
reaction |
1 | 5450-5453 | These two processes take place simultaneously in a
Fig 6 2:
Red ball represents the incoming hydroxide ion and green ball represents
the outgoing halide ion
In the year 1937,
Edward Davies Hughes
and Sir Christopher
Ingold
proposed
mechanism for an SN2a
reaction The solid wedge represents the bond coming out of the paper, dashed line going down the
paper and a straight line representing bond in the plane of the paper |
1 | 5451-5454 | 6 2:
Red ball represents the incoming hydroxide ion and green ball represents
the outgoing halide ion
In the year 1937,
Edward Davies Hughes
and Sir Christopher
Ingold
proposed
mechanism for an SN2a
reaction The solid wedge represents the bond coming out of the paper, dashed line going down the
paper and a straight line representing bond in the plane of the paper Rationalised 2023-24
172
Chemistry
single step and no intermediate is formed |
1 | 5452-5455 | 2:
Red ball represents the incoming hydroxide ion and green ball represents
the outgoing halide ion
In the year 1937,
Edward Davies Hughes
and Sir Christopher
Ingold
proposed
mechanism for an SN2a
reaction The solid wedge represents the bond coming out of the paper, dashed line going down the
paper and a straight line representing bond in the plane of the paper Rationalised 2023-24
172
Chemistry
single step and no intermediate is formed As the reaction progresses
and the bond between the incoming nucleophile and the carbon
atom starts forming, the bond between carbon atom and leaving
group weakens |
1 | 5453-5456 | The solid wedge represents the bond coming out of the paper, dashed line going down the
paper and a straight line representing bond in the plane of the paper Rationalised 2023-24
172
Chemistry
single step and no intermediate is formed As the reaction progresses
and the bond between the incoming nucleophile and the carbon
atom starts forming, the bond between carbon atom and leaving
group weakens As this happens, the three carbon-hydrogen bonds
of the substrate start moving away from the attacking nucleophile |
1 | 5454-5457 | Rationalised 2023-24
172
Chemistry
single step and no intermediate is formed As the reaction progresses
and the bond between the incoming nucleophile and the carbon
atom starts forming, the bond between carbon atom and leaving
group weakens As this happens, the three carbon-hydrogen bonds
of the substrate start moving away from the attacking nucleophile In
transition state all the three C-H bonds are in the same plane and the
attacking and leaving nucleophiles are partially attached to the
carbon |
1 | 5455-5458 | As the reaction progresses
and the bond between the incoming nucleophile and the carbon
atom starts forming, the bond between carbon atom and leaving
group weakens As this happens, the three carbon-hydrogen bonds
of the substrate start moving away from the attacking nucleophile In
transition state all the three C-H bonds are in the same plane and the
attacking and leaving nucleophiles are partially attached to the
carbon As the attacking nucleophile approaches closer to the carbon,
C-H bonds still keep on moving in the same direction till the attacking
nucleophile attaches to carbon and leaving group leaves the carbon |
1 | 5456-5459 | As this happens, the three carbon-hydrogen bonds
of the substrate start moving away from the attacking nucleophile In
transition state all the three C-H bonds are in the same plane and the
attacking and leaving nucleophiles are partially attached to the
carbon As the attacking nucleophile approaches closer to the carbon,
C-H bonds still keep on moving in the same direction till the attacking
nucleophile attaches to carbon and leaving group leaves the carbon As a result configuration is inverted, the configuration (See box) of
carbon atom under attack inverts in much the same way as an
umbrella is turned inside out when caught in a strong wind |
1 | 5457-5460 | In
transition state all the three C-H bonds are in the same plane and the
attacking and leaving nucleophiles are partially attached to the
carbon As the attacking nucleophile approaches closer to the carbon,
C-H bonds still keep on moving in the same direction till the attacking
nucleophile attaches to carbon and leaving group leaves the carbon As a result configuration is inverted, the configuration (See box) of
carbon atom under attack inverts in much the same way as an
umbrella is turned inside out when caught in a strong wind This
process is called as inversion of configuration |
1 | 5458-5461 | As the attacking nucleophile approaches closer to the carbon,
C-H bonds still keep on moving in the same direction till the attacking
nucleophile attaches to carbon and leaving group leaves the carbon As a result configuration is inverted, the configuration (See box) of
carbon atom under attack inverts in much the same way as an
umbrella is turned inside out when caught in a strong wind This
process is called as inversion of configuration In the transition
state, the carbon atom is simultaneously bonded to incoming
nucleophile and the outgoing leaving group |
1 | 5459-5462 | As a result configuration is inverted, the configuration (See box) of
carbon atom under attack inverts in much the same way as an
umbrella is turned inside out when caught in a strong wind This
process is called as inversion of configuration In the transition
state, the carbon atom is simultaneously bonded to incoming
nucleophile and the outgoing leaving group Such structures are
unstable and cannot be isolated |
1 | 5460-5463 | This
process is called as inversion of configuration In the transition
state, the carbon atom is simultaneously bonded to incoming
nucleophile and the outgoing leaving group Such structures are
unstable and cannot be isolated Thus, in the transition state, carbon
is simultaneously bonded to five atoms |
1 | 5461-5464 | In the transition
state, the carbon atom is simultaneously bonded to incoming
nucleophile and the outgoing leaving group Such structures are
unstable and cannot be isolated Thus, in the transition state, carbon
is simultaneously bonded to five atoms Hughes worked under
Ingold and earned a
D |
1 | 5462-5465 | Such structures are
unstable and cannot be isolated Thus, in the transition state, carbon
is simultaneously bonded to five atoms Hughes worked under
Ingold and earned a
D Sc |
1 | 5463-5466 | Thus, in the transition state, carbon
is simultaneously bonded to five atoms Hughes worked under
Ingold and earned a
D Sc degree from the
University of London |
1 | 5464-5467 | Hughes worked under
Ingold and earned a
D Sc degree from the
University of London Since this reaction requires the approach of the nucleophile to the
carbon bearing the leaving group, the presence of bulky substituents
on or near the carbon atom have a dramatic inhibiting effect |
1 | 5465-5468 | Sc degree from the
University of London Since this reaction requires the approach of the nucleophile to the
carbon bearing the leaving group, the presence of bulky substituents
on or near the carbon atom have a dramatic inhibiting effect Of the
simple alkyl halides, methyl halides react most rapidly in SN2 reactions
because there are only three small hydrogen atoms |
1 | 5466-5469 | degree from the
University of London Since this reaction requires the approach of the nucleophile to the
carbon bearing the leaving group, the presence of bulky substituents
on or near the carbon atom have a dramatic inhibiting effect Of the
simple alkyl halides, methyl halides react most rapidly in SN2 reactions
because there are only three small hydrogen atoms Tertiary halides
are the least reactive because bulky groups hinder the approaching
Configuration
Spacial arrangement of functional groups around carbon is called its configuration |
1 | 5467-5470 | Since this reaction requires the approach of the nucleophile to the
carbon bearing the leaving group, the presence of bulky substituents
on or near the carbon atom have a dramatic inhibiting effect Of the
simple alkyl halides, methyl halides react most rapidly in SN2 reactions
because there are only three small hydrogen atoms Tertiary halides
are the least reactive because bulky groups hinder the approaching
Configuration
Spacial arrangement of functional groups around carbon is called its configuration See the structures (A) and (B) given below carefully |
1 | 5468-5471 | Of the
simple alkyl halides, methyl halides react most rapidly in SN2 reactions
because there are only three small hydrogen atoms Tertiary halides
are the least reactive because bulky groups hinder the approaching
Configuration
Spacial arrangement of functional groups around carbon is called its configuration See the structures (A) and (B) given below carefully These are the two structures of the same compound |
1 | 5469-5472 | Tertiary halides
are the least reactive because bulky groups hinder the approaching
Configuration
Spacial arrangement of functional groups around carbon is called its configuration See the structures (A) and (B) given below carefully These are the two structures of the same compound They differ in spacial arrangement
of functional groups attached to carbon |
1 | 5470-5473 | See the structures (A) and (B) given below carefully These are the two structures of the same compound They differ in spacial arrangement
of functional groups attached to carbon Structure (A) is mirror image of Structure (B) |
1 | 5471-5474 | These are the two structures of the same compound They differ in spacial arrangement
of functional groups attached to carbon Structure (A) is mirror image of Structure (B) We say configuration of carbon in structure (A) is mirror image of the configuration of
carbon in structure (B) |
1 | 5472-5475 | They differ in spacial arrangement
of functional groups attached to carbon Structure (A) is mirror image of Structure (B) We say configuration of carbon in structure (A) is mirror image of the configuration of
carbon in structure (B) Rationalised 2023-24
173 Haloalkanes and Haloarenes
nucleophiles |
1 | 5473-5476 | Structure (A) is mirror image of Structure (B) We say configuration of carbon in structure (A) is mirror image of the configuration of
carbon in structure (B) Rationalised 2023-24
173 Haloalkanes and Haloarenes
nucleophiles Thus the order of reactivity followed is:
Primary halide > Secondary halide > Tertiary halide |
1 | 5474-5477 | We say configuration of carbon in structure (A) is mirror image of the configuration of
carbon in structure (B) Rationalised 2023-24
173 Haloalkanes and Haloarenes
nucleophiles Thus the order of reactivity followed is:
Primary halide > Secondary halide > Tertiary halide (b) Substitution nucleophilic unimolecular (SN1)
SN1 reactions are generally carried out in polar protic solvents
(like water, alcohol, acetic acid, etc |
1 | 5475-5478 | Rationalised 2023-24
173 Haloalkanes and Haloarenes
nucleophiles Thus the order of reactivity followed is:
Primary halide > Secondary halide > Tertiary halide (b) Substitution nucleophilic unimolecular (SN1)
SN1 reactions are generally carried out in polar protic solvents
(like water, alcohol, acetic acid, etc ) |
1 | 5476-5479 | Thus the order of reactivity followed is:
Primary halide > Secondary halide > Tertiary halide (b) Substitution nucleophilic unimolecular (SN1)
SN1 reactions are generally carried out in polar protic solvents
(like water, alcohol, acetic acid, etc ) The reaction between tert-
butyl bromide and hydroxide ion yields tert-butyl alcohol and
follows the first order kinetics, i |
1 | 5477-5480 | (b) Substitution nucleophilic unimolecular (SN1)
SN1 reactions are generally carried out in polar protic solvents
(like water, alcohol, acetic acid, etc ) The reaction between tert-
butyl bromide and hydroxide ion yields tert-butyl alcohol and
follows the first order kinetics, i e |
1 | 5478-5481 | ) The reaction between tert-
butyl bromide and hydroxide ion yields tert-butyl alcohol and
follows the first order kinetics, i e , the rate of reaction depends
upon the concentration of only one reactant, which is tert- butyl
bromide |
1 | 5479-5482 | The reaction between tert-
butyl bromide and hydroxide ion yields tert-butyl alcohol and
follows the first order kinetics, i e , the rate of reaction depends
upon the concentration of only one reactant, which is tert- butyl
bromide It occurs in two steps |
1 | 5480-5483 | e , the rate of reaction depends
upon the concentration of only one reactant, which is tert- butyl
bromide It occurs in two steps In step I, the polarised C—Br bond undergoes
slow cleavage to produce a carbocation and a bromide ion |
1 | 5481-5484 | , the rate of reaction depends
upon the concentration of only one reactant, which is tert- butyl
bromide It occurs in two steps In step I, the polarised C—Br bond undergoes
slow cleavage to produce a carbocation and a bromide ion The
carbocation thus formed is then attacked by nucleophile in step II
to complete the substitution reaction |
1 | 5482-5485 | It occurs in two steps In step I, the polarised C—Br bond undergoes
slow cleavage to produce a carbocation and a bromide ion The
carbocation thus formed is then attacked by nucleophile in step II
to complete the substitution reaction Fig |
1 | 5483-5486 | In step I, the polarised C—Br bond undergoes
slow cleavage to produce a carbocation and a bromide ion The
carbocation thus formed is then attacked by nucleophile in step II
to complete the substitution reaction Fig 6 |
1 | 5484-5487 | The
carbocation thus formed is then attacked by nucleophile in step II
to complete the substitution reaction Fig 6 3: Steric effects in SN2 reaction |
1 | 5485-5488 | Fig 6 3: Steric effects in SN2 reaction The relative rate of SN2 reaction is given in parenthesis
Rationalised 2023-24
174
Chemistry
Step I is the slowest and reversible |
1 | 5486-5489 | 6 3: Steric effects in SN2 reaction The relative rate of SN2 reaction is given in parenthesis
Rationalised 2023-24
174
Chemistry
Step I is the slowest and reversible It involves the C–Br bond breaking for which the
energy is obtained through solvation of halide ion with the proton of protic solvent |
1 | 5487-5490 | 3: Steric effects in SN2 reaction The relative rate of SN2 reaction is given in parenthesis
Rationalised 2023-24
174
Chemistry
Step I is the slowest and reversible It involves the C–Br bond breaking for which the
energy is obtained through solvation of halide ion with the proton of protic solvent Since
the rate of reaction depends upon the slowest step, the rate of reaction depends only on the
concentration of alkyl halide and not on the concentration of hydroxide ion |
1 | 5488-5491 | The relative rate of SN2 reaction is given in parenthesis
Rationalised 2023-24
174
Chemistry
Step I is the slowest and reversible It involves the C–Br bond breaking for which the
energy is obtained through solvation of halide ion with the proton of protic solvent Since
the rate of reaction depends upon the slowest step, the rate of reaction depends only on the
concentration of alkyl halide and not on the concentration of hydroxide ion Further, greater
the stability of carbocation, greater will be its ease of formation from alkyl halide and faster
will be the rate of reaction |
1 | 5489-5492 | It involves the C–Br bond breaking for which the
energy is obtained through solvation of halide ion with the proton of protic solvent Since
the rate of reaction depends upon the slowest step, the rate of reaction depends only on the
concentration of alkyl halide and not on the concentration of hydroxide ion Further, greater
the stability of carbocation, greater will be its ease of formation from alkyl halide and faster
will be the rate of reaction In case of alkyl halides, 3
0 alkyl halides undergo SN1 reaction
very fast because of the high stability of 3
0 carbocations |
1 | 5490-5493 | Since
the rate of reaction depends upon the slowest step, the rate of reaction depends only on the
concentration of alkyl halide and not on the concentration of hydroxide ion Further, greater
the stability of carbocation, greater will be its ease of formation from alkyl halide and faster
will be the rate of reaction In case of alkyl halides, 3
0 alkyl halides undergo SN1 reaction
very fast because of the high stability of 3
0 carbocations We can sum up the order of reactivity
of alkyl halides towards SN1 and SN2 reactions as follows:
For the same reasons, allylic and benzylic halides show high reactivity towards the SN1
reaction |
1 | 5491-5494 | Further, greater
the stability of carbocation, greater will be its ease of formation from alkyl halide and faster
will be the rate of reaction In case of alkyl halides, 3
0 alkyl halides undergo SN1 reaction
very fast because of the high stability of 3
0 carbocations We can sum up the order of reactivity
of alkyl halides towards SN1 and SN2 reactions as follows:
For the same reasons, allylic and benzylic halides show high reactivity towards the SN1
reaction The carbocation thus formed gets stabilised through resonance (Unit 8, Class XI) as
shown below:
In the following pairs of halogen compounds, which would undergo
SN2 reaction faster |
1 | 5492-5495 | In case of alkyl halides, 3
0 alkyl halides undergo SN1 reaction
very fast because of the high stability of 3
0 carbocations We can sum up the order of reactivity
of alkyl halides towards SN1 and SN2 reactions as follows:
For the same reasons, allylic and benzylic halides show high reactivity towards the SN1
reaction The carbocation thus formed gets stabilised through resonance (Unit 8, Class XI) as
shown below:
In the following pairs of halogen compounds, which would undergo
SN2 reaction faster Example 6 |
1 | 5493-5496 | We can sum up the order of reactivity
of alkyl halides towards SN1 and SN2 reactions as follows:
For the same reasons, allylic and benzylic halides show high reactivity towards the SN1
reaction The carbocation thus formed gets stabilised through resonance (Unit 8, Class XI) as
shown below:
In the following pairs of halogen compounds, which would undergo
SN2 reaction faster Example 6 6
Example 6 |
1 | 5494-5497 | The carbocation thus formed gets stabilised through resonance (Unit 8, Class XI) as
shown below:
In the following pairs of halogen compounds, which would undergo
SN2 reaction faster Example 6 6
Example 6 6
Example 6 |
1 | 5495-5498 | Example 6 6
Example 6 6
Example 6 6
Example 6 |
1 | 5496-5499 | 6
Example 6 6
Example 6 6
Example 6 6
Example 6 |
1 | 5497-5500 | 6
Example 6 6
Example 6 6
Example 6 6
H2C
2
C
CH
H
+
H2C
CH2
C
H
+
Solution
Solution
Solution
Solution
Solution
It is primary halide and therefore undergoes SN2
reaction faster |
1 | 5498-5501 | 6
Example 6 6
Example 6 6
H2C
2
C
CH
H
+
H2C
CH2
C
H
+
Solution
Solution
Solution
Solution
Solution
It is primary halide and therefore undergoes SN2
reaction faster As iodine is a better leaving group because of its
large size, it will be released at a faster rate in the
presence of incoming nucleophile |
1 | 5499-5502 | 6
Example 6 6
H2C
2
C
CH
H
+
H2C
CH2
C
H
+
Solution
Solution
Solution
Solution
Solution
It is primary halide and therefore undergoes SN2
reaction faster As iodine is a better leaving group because of its
large size, it will be released at a faster rate in the
presence of incoming nucleophile Example 6 |
1 | 5500-5503 | 6
H2C
2
C
CH
H
+
H2C
CH2
C
H
+
Solution
Solution
Solution
Solution
Solution
It is primary halide and therefore undergoes SN2
reaction faster As iodine is a better leaving group because of its
large size, it will be released at a faster rate in the
presence of incoming nucleophile Example 6 7
Example 6 |
1 | 5501-5504 | As iodine is a better leaving group because of its
large size, it will be released at a faster rate in the
presence of incoming nucleophile Example 6 7
Example 6 7
Example 6 |
1 | 5502-5505 | Example 6 7
Example 6 7
Example 6 7
Example 6 |
1 | 5503-5506 | 7
Example 6 7
Example 6 7
Example 6 7
Example 6 |
1 | 5504-5507 | 7
Example 6 7
Example 6 7
Example 6 7
Predict the order of reactivity of the following
compounds in SN1 and SN2 reactions:
(i) The four isomeric bromobutanes
(ii) C6H5CH2Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br, C6H5C(CH3)(C6H5)Br
For a given alkyl group, the reactivity of the halide, R-X, follows the same order in both the
mechanisms R–I> R–Br>R–Cl>>R–F |
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