Concept explainers
(a)
Interpretation:
Whether the product of the given step can eliminate a leaving group to form a different compound than the reactant is to be predicted. The product for the given nucleophilic elimination step with appropriate curved arrows is to be drawn.
Concept introduction:
In the nucleophilic elimination step, the more electronegative atom bears full or partial negative charge. This is an electron rich atom, and the less electronegative atom is relatively electron poor. The curved arrow drawn from the lone pair of electron rich atom points to the bonding region between the more electronegative atom and less electronegative atom representing the electron flow from the electron rich site to the electron poor site. The second curved arrow is drawn to represent the breaking of the bond between the less electronegative atom and leaving group to avoid exceeding an octet on the less electronegative atom.
Answer to Problem 7.27P
Products formed after the elimination of the leaving group are not the same as the reactant. Product formed in the nucleophilic elimination step with appropriate curved arrows is drawn as:
Explanation of Solution
Product for the given nucleophilic addition step is:
In the given product, there are two possible groups that can leave to form two different products.
In the first nucleophilic elimination step, the oxygen atom with negative charge is an electron rich site, and the carbon bonded to it is an electron poor site. The curved arrow mechanism for this given nucleophilic elimination step forming the respective product is:
The first curved arrow is drawn from the lone pair of negatively charged oxygen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step. The X sign on the arrow represents that this nucleophilic elimination is unfeasible as
In the second nucleophilic elimination step, the oxygen atom with negative charge is the electron rich site, and the carbon bonded to it is the electron poor site. The curved arrow mechanism for this given nucleophilic elimination step forming the respective product is:
The first curve arrow is drawn from the lone pair of negatively charged oxygen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step. The X sign on the arrow represents that this nucleophilic elimination is unfeasible as
Products formed in the elimination steps are different from the reactant in the given nucleophilic addition step.
(b)
Interpretation:
Whether the product of the given step can eliminate a leaving group to form a different compound than the reactant is to be predicted. The product for the given nucleophilic elimination step with appropriate curved arrows is to be drawn.
Concept introduction:
In the nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This is the electron rich atom and the less electronegative atom is relatively electron poor. The curved arrow drawn from the lone pair of electron rich atom points to the bonding region between the more electronegative atom and less electronegative atom representing the electron flow from the electron rich site to the electron poor site. The second curved arrow is drawn to represent the breaking of bond between the less electronegative atom and leaving group to avoid exceeding an octet on the less electronegative atom.
Answer to Problem 7.27P
The product formed after the elimination of the leaving group is not the same as the reactant. Product formed in the nucleophilic elimination step with an appropriate curved arrow is drawn as:
Explanation of Solution
Product for the given nucleophilic addition step is:
In the nucleophilic elimination step, the oxygen atom with negative charge is an electron rich site, and the carbon bonded to it is an electron poor site. The curved arrow mechanism for this given nucleophilic elimination step forming the respective product is:
The first curved arrow is drawn from the lone pair of negatively charged oxygen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step. The X sign on the arrow represents this nucleophilic elimination is unfeasible as
Product formed in the elimination step is different from the reactant in the given nucleophilic addition step.
(c)
Interpretation:
The product of the given step can eliminate a leaving group to form different compound than reactant is to be predicted. The product for the given nucleophilic elimination step with appropriate curved arrows is to be drawn.
Concept introduction:
In nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This is the electron rich atom and the less electronegative atom is relatively electron poor. The curved arrow drawn from the lone pair of electron rich atom points to the bonding region between the more electronegative atom and less electronegative atom representing the electron flow from electron rich site to electron poor site. The second curved arrow drawn to represent the breaking of bond between the less electronegative atom and leaving group to avoid exceeding an octet on the less electronegative atom.
Answer to Problem 7.27P
The products formed after the elimination of the leaving group are not the same as the reactant. Product formed in the nucleophilic elimination step with appropriate curved arrow is drawn as:
Explanation of Solution
Product for the given nucleophilic addition step is:
In the nucleophilic elimination step, the nitrogen atom with negative charge is electron rich site, and the carbon bonded to it is electron poor site. The curved arrow mechanism for this given nucleophilic elimination step forming the respective product is:
The first curved arrow is drawn from the lone pair of negatively charged nitrogen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step. The X sign on the arrow represents this nucleophilic elimination is unfeasible as
Product formed in the elimination step is different from the reactant in the given nucleophilic addition step.
(d)
Interpretation:
Whether the product of the given step can eliminate a leaving group to form different compound than reactant is to be predicted. The product for the given nucleophilic elimination step with appropriate curved arrows is to be drawn.
Concept introduction:
In nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This is the electron rich atom and the less electronegative atom is relatively electron poor. The curved arrow drawn from the lone pair of electron rich atom points to the bonding region between the more electronegative atom and less electronegative atom representing the electron flow from electron rich site to electron poor site. The second curved arrow is drawn to represent the breaking of bond between the less electronegative atom and leaving group to avoid exceeding an octet on the less electronegative atom.
Answer to Problem 7.27P
Products formed after the elimination of the leaving group are not the same as the reactant. Product formed in the nucleophilic elimination step with appropriate curved arrow is drawn as:
Explanation of Solution
Product for the given nucleophilic addition step is:
In the first nucleophilic elimination step, the oxygen atom with negative charge is electron rich site, and the chlorine atom is a good leaving group. The curved arrow mechanism for this given nucleophilic elimination step forming the respective product is:
The first curved arrow is drawn from the lone pair of negatively charged oxygen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step.
In the second nucleophilic elimination step, the oxygen atom with negative charge is electron rich site and the carbon bonded to it is electron poor site. The curved arrow mechanism for this given nucleophilic elimination step forming the respective product is:
The first curved arrow is drawn from the lone pair of negatively charged oxygen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step. The X sign on the arrow represents this nucleophilic elimination is unfeasible as
Products formed in the elimination steps are different from the reactant in the given nucleophilic addition step.
(e)
Interpretation:
Whether the product of the given step can eliminate a leaving group to form different compound than reactant is to be predicted. The product for the given nucleophilic elimination step with appropriate curved arrows is to be drawn.
Concept introduction:
In nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This is the electron rich atom and the less electronegative atom is relatively electron poor. The curved arrow is drawn from the lone pair of electron rich atom points to the bonding region between the more electronegative atom and less electronegative atom representing the electron flow from electron rich site to electron poor site. The second curved arrow is drawn to represent the breaking of bond between the less electronegative atom and leaving group to avoid exceeding an octet on the less electronegative atom.
Answer to Problem 7.27P
Products formed after the elimination of the leaving group are not same as the reactant. Product formed in the nucleophilic elimination step with appropriate curved arrow is drawn as:
Explanation of Solution
Product for the given nucleophilic addition step is:
In the given product, there are two possible groups that can leave to form two different products.
In the first nucleophilic elimination step, the oxygen atom with negative charge is electron rich site, and the carbon bonded to it is electron poor site. The curved arrow mechanism for this given nucleophilic elimination step forming the respective product is:
The first curved arrow is drawn from the lone pair of negatively charged oxygen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step. The X sign on the arrow represents this nucleophilic elimination is unfeasible as
In the second nucleophilic elimination step, the oxygen atom with negative charge is electron rich site and
The first curved arrow is drawn from the lone pair of negatively charged oxygen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step.
Products formed in the elimination steps are different from the reactant in the given nucleophilic addition step.
(f)
Interpretation:
Whether the product of the given step can eliminate a leaving group to form different compound than reactant is to be predicted. The product for the given nucleophilic elimination step with appropriate curved arrows is to be drawn.
Concept introduction:
In nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This is the electron rich atom and the less electronegative atom is relatively electron poor. The curved arrow drawn from the lone pair of electron rich atom points to bonding region between the more electronegative atom and less electronegative atom representing the electron flow from electron rich site to electron poor site. The second curved arrow is drawn to represent the breaking of bond between the less electronegative atom and leaving group to avoid exceeding an octet on the less electronegative atom.
Answer to Problem 7.27P
Products formed after the elimination of the leaving group are not same as the reactant. Product formed in the nucleophilic elimination step with appropriate curved arrow is drawn as:
Explanation of Solution
Product for the given nucleophilic addition step is:
In the given product, there are two possible groups that can leave to form two different products.
In the first nucleophilic elimination step, the oxygen atom with negative charge is electron rich site and the carbon bonded to it is electron poor site. The curved arrow mechanism for this given nucleophilic elimination step forming the respective product is:
The first curved arrow is drawn from the lone pair of negatively charged oxygen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step. The X sign on the arrow represents this nucleophilic elimination is unfeasible as
The second nucleophilic elimination step, the oxygen atom with negative charge is electron rich site and the carbon bonded to it is electron poor site. The curved arrow mechanism for this given nucleophilic elimination step forming the respective product is:
The first curved arrow is drawn from the lone pair of negatively charged oxygen to the mid of
The respective product formed is different from the reactant in the given nucleophilic addition step. The X sign on the arrow represents this nucleophilic elimination is unfeasible as
Products formed in the elimination steps are different from the reactant in the given nucleophilic addition step.
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Chapter 7 Solutions
ORGANIC CHEMISTRY:PRINCIPLES...(CL)
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- Find the error in the given answer? Question: For the given starting material, draw the product of the following reaction series.arrow_forwardIdentify the stronger nucleophile in the following pair of anions. HS− or F− in a polar protic solventarrow_forwardIdentify the stronger nucleophile in the following pair of anions. Br− or Cl− in a polar protic solventarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning