Concept explainers
Consider the following
a. Draw a mechanism using curved arrows.
b. Draw an energy diagram. Label the axes, the reactants, products,
c. Draw the structure of the transition state.
d. What is the rate equation?
e. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from
(a)
Interpretation: The mechanism of the given reaction is to be drawn by the use of curved arrows.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.
Answer to Problem 7.53P
The mechanism of the given reaction is,
Explanation of Solution
The structure of the given alkyl halide shows that carbon atom, on which bromine is present, is bonded to one another carbon atom. Hence, the bromine atom is bonded to primary carbon atom and the given alkyl halide is
In
Figure 1
The mechanism of the given reaction is shown in Figure 1.
(b)
Interpretation: The energy diagram is to be drawn. The axes, reactants, products,
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The graphical representation of chemical reaction in which x-axis represents energy of the reaction and y-axis represents the reaction coordinate is called energy profile diagram.
Answer to Problem 7.53P
The energy diagram of the given reaction is shown below.
Explanation of Solution
In bimolecular nucleophilic substitution reaction, formation and breakage of bond takes place simultaneously in the transition state. In the given reaction, breakage of
The energy of products is lower than the energy of reactants in exothermic reaction. Therefore, the energy diagram of the given reaction is,
Figure 2
The x-axes of the energy diagram represent the energy of reactants and products and y-axes represent the reaction coordinate.
The energy diagram of the given reaction is shown in Figure 2.
(c)
Interpretation: The structure of the transition state is to be drawn.
Concept introduction: In bimolecular nucleophilic substitution reaction, formation and breakage of bond takes place simultaneously in the transition state. The energy of transition state is more than the energy of reactants and products.
Answer to Problem 7.53P
The structure of the transition state is shown below.
Explanation of Solution
In bimolecular nucleophilic substitution reaction, formation and breakage of bond takes place simultaneously in the transition state. In the given reaction, breakage of
Therefore, the transition state of the given reaction is,
Figure 3
The structure of the transition state is shown in Figure 3.
(d)
Interpretation: The rate equation of the given reaction is to be predicted.
Concept introduction: The rate of
The rate equation of
Answer to Problem 7.53P
The rate equation of the given reaction is,
Explanation of Solution
The rate of
The rate equation of
The alkyl halide of given reaction is
Therefore, the rate equation of given reaction is,
The rate equation of the given reaction is,
(e)
Interpretation: The change that occurs to the reaction rate in given instances is to be stated.
Concept introduction: The rate of
The rate of
Answer to Problem 7.53P
The change that occurs to the reaction rate in given instances is,
[1] The rate of the reaction will increase.
[2] The rate of the reaction will decrease.
[3] The rate of the reaction will decrease.
[4] The rate of the reaction increases by five times.
[5] The rate of the reaction increases by twenty five times.
Explanation of Solution
[1]
The primary halide undergoes nucleophilic substitution by
[2]
The polar protic solvent favors
[3]
The primary halide undergoes nucleophilic substitution by
[4]
The rate of
The rate of
According the given statement, the concentration of
Therefore, the rate of the reaction increases by five times when the concentration of
[5]
The rate of
The rate of
According the given statement, the concentration of
Therefore, the rate of the reaction increases by twenty five times when the concentration
The change that occurs to the reaction rate in given instances is,
[1] The rate of the reaction will increase.
[2] The rate of the reaction will decrease.
[3] The rate of the reaction will decrease.
[4] The rate of the reaction increases by five times.
[5] The rate of the reaction increases by twenty five times.
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