
Concept explainers
(a)
Interpretation:
The product on reaction of
Concept introduction:
The replacement or substitution of one

Answer to Problem 18.46AP
No product is formed on reaction of
Explanation of Solution
The reaction of
Figure 1
Aryl iodides cannot undergo nucleophilic substitution reaction. Aryl iodides neither undergo
There is no product formed on reaction of
(b)
Interpretation:
The product on reaction of
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 nucleophile. In nucleophilc acyl substitution reaction, nucleophile takes the position of leaving group.

Answer to Problem 18.46AP
No product is formed on reaction of
Explanation of Solution
The reaction of
Figure 2
Aryl iodides cannot undergo nucleophilic substitution reaction. Aryl iodides neither undergo
There is no product formed on reaction of
(c)
Interpretation:
The product on reaction of
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 nucleophile. In nucleophilc acyl substitution reaction, nucleophile takes the position of leaving group.

Answer to Problem 18.46AP
No product is formed on reaction of
Explanation of Solution
The product on reaction of
Figure 3
Aryl iodides cannot undergo nucleophilic substitution reaction. Aryl iodides neither undergo
There is no product formed on reaction of
(d)
Interpretation:
The product on reaction of
Concept introduction:
Grignard reagents are

Answer to Problem 18.46AP
The product on reaction of
Explanation of Solution
The reaction of
Figure 4
In the above reaction, magnesium gets inserted in the carbon-halogen bond to form a Grignard reagent. THF is used as the reaction should be done in anhydrous and inert condition. Therefore, the product formed on reaction of
Figure 5
The reaction of
(e)
Interpretation:
The product on reaction of the product formed in part (d) with
Concept introduction:
Stille reaction is an example of coupling reaction. In Stille reaction, the triflate reacts with trimethylstannane in presence of

Answer to Problem 18.46AP
The product on reaction of the product formed in part (d) with
Explanation of Solution
The product formed in part (d) is shown below.
Figure 5
The reaction of the product formed in part (d) with
Figure 6
In the above reaction, a stannane compound is formed on reaction of a Grignard reagent with
Figure 7
The product on reaction of the product formed in part (d) with
(f)
Interpretation:
The product on reaction of
Concept introduction:
Alkyl lithium is an organolithium reagent. It contains carbon-lithium bond. It is used in

Answer to Problem 18.46AP
The product on reaction of
Explanation of Solution
The reaction of
Figure 8
The above reaction is known as lithium-halogen exchange reaction. The reaction occurs under inert conditions. In this reaction, two moles of lithium react with
Figure 9
The product on reaction of
(g)
Interpretation:
The product on reaction of
Concept introduction:
The treatment of an organic halide with an

Answer to Problem 18.46AP
The product on reaction of
Explanation of Solution
The reaction of
Figure 10
In the above reaction a coupled product is formed. The coupling takes place between ethene and
Figure 11
The product on reaction of
(h)
Interpretation:
The product on reaction of product of part (e) with phenyl triflate, excess
Concept introduction:
Stille reaction is an example of coupling reaction. In Stille reaction, the triflate reacts with trimethylstannane in presence of

Answer to Problem 18.46AP
The product on reaction of product of part (e) with phenyl triflate, excess
Explanation of Solution
The product formed in part (e) is shown below.
Figure 7
The reaction of above compound with phenyl triflate, excess
Figure 12
The above reaction is an example of Stille coupling reaction. In this reaction a triflate reacts with stannane compound in presence of
Figure 13
The product on reaction of product of part (e) with phenyl triflate, excess
(i)
Interpretation:
The product on reaction of
Concept introduction:
The Suzuki coupling reaction is a reaction in which an aryl or vinylic boronic acid is coupled to an aryl or vinylic iodide or bromide. It is a

Answer to Problem 18.46AP
The product on reaction of
Explanation of Solution
The reaction of
Figure 14
In the above reaction,
Figure 15
The product on reaction of
(j)
Interpretation:
The product on reaction of product of part (d) with
Concept introduction:
The Suzuki coupling reaction in which an aryl or vinylic boronic acid is coupled to an aryl or vinylic iodide or bromide. It is a

Answer to Problem 18.46AP
The product of part (d) with
Explanation of Solution
The product of part (d) is shown below.
Figure 5
The reaction of product of part (d) with
Figure 16
In the above reaction,
Figure 17
The product of part (d) with
(k)
Interpretation:
The product on reaction of product of part (j) with
Concept introduction:
The Suzuki coupling reaction in which an aryl or vinylic boronic acid is coupled to an aryl or vinylic iodide or bromide. It is a

Answer to Problem 18.46AP
The product on reaction of product of part (j) with
Explanation of Solution
The product of part (j) is shown below.
Figure 17
The reaction of product of part (j) with
Figure 18
The above reaction is Suzuki coupling reaction. In this reaction,
Figure 19
The product on reaction of product of part (j) with
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Chapter 18 Solutions
Organic Chemistry Study Guide and Solutions
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- Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
