(a)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any
Answer to Problem 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given
In
However, in the given reaction halogen atom is not attached to chiral carbon. It is bonded to non-chiral carbon atom. The attack of nucleophile has not affect on the stereochemistry of reactant as shown in Figure 1.
Figure 1
The stereochemistry of reactant and product is same.
The mechanism of given nucleophilic substitution reaction is
(b)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
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 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that a carbon atom, on which bromine atom is present, is bonded to two other carbon atoms. Hence, the bromine atom is bonded to secondary carbon atom. The removal of bromine atom leads to the formation of secondary carbocation. The secondary carbocation can undergo nucleophilic substitution reaction through both
In
Figure 2
The mechanism of given nucleophilic substitution reaction is
(c)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
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 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that carbon atom, on which bromine atom is present, is bonded to three other carbon atoms. Hence, the bromine atom is bonded to tertiary carbon atom. The removal of bromine atom leads to the formation of planer tertiary carbocation. The tertiary carbocation is most likely to undergo nucleophilic substitution reaction by
In
Figure 3
The mechanism of given nucleophilic substitution reaction is
(d)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
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 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that a carbon atom, on which iodine atom is present, is bonded to two other carbon atoms. Hence, the iodine atom is bonded to secondary carbon atom. The removal of iodine atom leads to the formation of secondary carbocation. The secondary carbocation can undergo nucleophilic substitution reaction through both
In
Figure 4
The mechanism of given nucleophilic substitution reaction is
(e)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
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 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that a carbon atom, on which bromine atom is present, is bonded to two other carbon atoms. Hence, the bromine atom is bonded to secondary carbon atom. The removal of bromine atom leads to the formation of secondary carbocation. The secondary carbocation can undergo nucleophilic substitution reaction through both
In
Figure 5
The mechanism of given nucleophilic substitution reaction is
(f)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
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 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that a carbon atom, on which bromine atom is present, is bonded to two other carbon atoms. Hence, the bromine atom is bonded to secondary carbon atom. The removal of bromine atom leads to the formation of secondary carbocation. The secondary carbocation can undergo nucleophilic substitution reaction through both
In
Figure 6
The mechanism of given nucleophilic substitution reaction is
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Chapter 7 Solutions
ORGANIC CHEMISTRY-STUDY GDE...-W/ACCESS
- Determining the Mechanism of Nucleophilic Substitution Determine the mechanism of nucleophilic substitution for each reaction and draw the products.arrow_forwardDraw the products of each reaction and indicate the stereochemistry where appropriate.arrow_forwardDetermining the Mechanism and Stereochemistry in Nucleophilic Substitution Determine the mechanism of nucleophilic substitution for each reaction and draw the products, including stereochemistry.arrow_forward
- Draw the products of each reaction and indicate their stereochemistry.arrow_forwardDraw the product for each substitution reaction. Provide stereochemistry where appropriate. Indicate if the reaction proceeds via SN1 or SN2arrow_forwardPlease draw the products for each nucleophilic substitution reaction. If there is no product, state why.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning