Concept explainers
Interpretation:
The compound, which reacts faster with sodium methoxide in methanol in each of the given pair of compounds is to be determined and the chemical equation for the faster reaction is to be written.
Concept introduction:
Nucleophilic
In nucleophilic aromatic substitution reactions, the nucleophile substitutes a leaving group from the aryl ring.
Aryl halides bearing an electron withdrawing substituent undergo nucleophilic substitution rapidly.
The substituents attached ortho and para with respect to the halogen atom in the aryl halide react at similar rates. The substituents attached at meta position in the aryl halide react at slower rates than ortho and para substituents.
Electron withdrawing substituents stabilize the intermediate carbanion formed and thus are strongly activating substituents in the nucleophilic aromatic substitution reactions.
Electron donating substituents destabilize the intermediate carbanion formed and thus are strongly deactivating substituents in the nucleophilic aromatic substitution reactions.
Answer to Problem 43P
Solution:
a)
The reaction is as follows:
b) In between
The reaction is as follows:
c) In between
The reaction is as follows:
d) In between
The reaction is as follows:
e) In between
The reaction is as follows:
Explanation of Solution
a)
In this nucleophilic aromatic substitution reaction, sodium methoxide is a source of the nucleophile
In chlorobenzene, a chlorine atom is attached to the benzene ring while in
The reaction of
b)
In this nucleophilic aromatic substitution reaction, sodium methoxide is a source of the nucleophile
In both the given aryl halides, a strong electron withdrawing substituent is attached on the ring. In
The reaction of
c)
In this nucleophilic aromatic substitution reaction, sodium methoxide is a source of the nucleophile
In
In
Thus, in between
The reaction of
d)
In this nucleophilic aromatic substitution reaction, sodium methoxide is a source of the nucleophile
Nitro substituents are strong electron withdrawing substituents.
In
Electron withdrawing substituents at ortho and para positions activate the ring more than the electron withdrawing substituents at meta positions.
Thus, in between
The reaction of
e)
In this nucleophilic aromatic substitution reaction, sodium methoxide is a source of the nucleophile
In
The reaction of
Want to see more full solutions like this?
Chapter 13 Solutions
Organic Chemistry - Standalone book
- What is the role of phosphoric acid in the synthesis of cyclohexene? it is an antioxidant that prevents free radical side reactions it is a safe, non-toxic solvent it lowers the boiling point of the reaction mixture (a colligative property of adding phosphoric acid to water) it protonates the hydroxyl of cyclohexanol to make it a better leaving grouparrow_forwardAcetals are formed from the reaction of two alcohols with a carbonyl under acidic conditions. Acetal formation is faster with 1,2-ethanediol than with two methanol molecules. Choose the factor that explains the difference in reaction rates. A) The reaction with 1,2-ethanediol has a lower AH (enthalpy) of reaction. B) The reaction with 1,2-ethanediol has a higher AH (enthalpy) of reaction. C) The reaction with 1,2-ethanediol has a more favorable entropy of reaction.arrow_forwardThe following molecule can undergo keto–enol tautomerization upon addition of hydroxide. Draw the structure of the enol form and the mechanism by which it forms.arrow_forward
- Which of the following sequences of reactions would convert toluene to 2-bromo-4-cyanotoluene? Bromination, nitration, reduction, diazotization, reaction with cyanide anion Bromination, nitration, diazotization, reduction , reaction with cyanide anion Nitration, bromination, reduction, diazotization, reaction with cyanide anion Nitration, bromination, diazotization, reduction, reaction with cyanide anionarrow_forwardWhich of the following compounds will NOT undergo nucleophilic substitution reaction? isopropanol Benzoyl chloride propylene oxide butanonearrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone –arrow_forward
- Draw the principal organic product for the reaction of 1-bromopentane with lithium in diethyl ether, followed by formaldehyde in diethyl ether, and then followed by dilute acid.arrow_forwardWhat reactions and reagents can be used to make phenol from benzene if electrophilic aromatic substitution reactions are excluded and benzene is the only source of carbon?arrow_forwardWhen cyclohexene is reacted with hydrobromic acid in acetic acid, the major product is bromocyclohexane. There is a small amount of cyclohexyl acetate formed. What is the mechanism that forms both compounds? What is the purification procedure that isolates both compounds?arrow_forward
- Predict the starting material or reagents needed to carry out the desired reactions.arrow_forwardWhich of the compounds listed will not undergo nucleophilic aromatic substitution? O 1-chloro-2,4-dinitrobenzene O 1-bromo-4-nitrobenzene O o-chloronitrobenzene m-chloronitrobenzene O p-chloronitrobenzenearrow_forwardGive the products when Ethyl Chloride reacts with Benzene in the presence of the catalyst Chlorobenzene + HCl + AlCl3 Ethylbenzene + HCl + AlCl3 Chlorobenzene + HCl+ FeCl3 Ethylbenzene + HCl + FeCl3arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning