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Which one of the following compounds is resistant to nucleophilic attack by hydroxyl ions?
- a)Methyl acetate
- b)Acetonitrile [1998]
- c)Diethyl ether
- d)Acetamide
Correct answer is option 'C'. Can you explain this answer?
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Which one of the following compounds is resistant to nucleophilic atta...
The compound is diethyl ether (CH3CH2)2O which is resistant to nucleophilic attack by hydroxyl ion due to absent of double or triple bond, whereas all other compounds given are unsaturated
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Which one of the following compounds is resistant to nucleophilic atta...
Resistant to nucleophilic attack by hydroxyl ions: Diethyl ether
Nucleophilic attack is a chemical reaction in which an electron-rich nucleophile attacks an electron-deficient electrophile, resulting in the formation of a new chemical bond. Hydroxyl ions (OH-) are a common nucleophile.
Diethyl ether is resistant to nucleophilic attack by hydroxyl ions due to the following reasons:
- Lack of a polar functional group: Diethyl ether is a simple ether, which lacks a polar functional group such as carbonyl or carboxyl that can easily undergo nucleophilic attack. This makes it less susceptible to nucleophilic attack by hydroxyl ions.
- Weak basicity: Diethyl ether is a weakly basic molecule, which means it has a low tendency to attract protons or accept electrons. This makes it less likely to react with hydroxyl ions, which are strong bases.
- Steric hindrance: The ethyl groups in diethyl ether create steric hindrance, which means they hinder the approach of nucleophiles such as hydroxyl ions. This makes it more difficult for hydroxyl ions to attack diethyl ether.
In contrast, methyl acetate, acetamide, and acetonitrile all contain polar functional groups that can easily undergo nucleophilic attack by hydroxyl ions. Therefore, they are more susceptible to nucleophilic attack than diethyl ether.
Overall, diethyl ether is a relatively inert compound that is resistant to nucleophilic attack by hydroxyl ions, making it a useful solvent in many chemical reactions.
Nucleophilic attack is a chemical reaction in which an electron-rich nucleophile attacks an electron-deficient electrophile, resulting in the formation of a new chemical bond. Hydroxyl ions (OH-) are a common nucleophile.
Diethyl ether is resistant to nucleophilic attack by hydroxyl ions due to the following reasons:
- Lack of a polar functional group: Diethyl ether is a simple ether, which lacks a polar functional group such as carbonyl or carboxyl that can easily undergo nucleophilic attack. This makes it less susceptible to nucleophilic attack by hydroxyl ions.
- Weak basicity: Diethyl ether is a weakly basic molecule, which means it has a low tendency to attract protons or accept electrons. This makes it less likely to react with hydroxyl ions, which are strong bases.
- Steric hindrance: The ethyl groups in diethyl ether create steric hindrance, which means they hinder the approach of nucleophiles such as hydroxyl ions. This makes it more difficult for hydroxyl ions to attack diethyl ether.
In contrast, methyl acetate, acetamide, and acetonitrile all contain polar functional groups that can easily undergo nucleophilic attack by hydroxyl ions. Therefore, they are more susceptible to nucleophilic attack than diethyl ether.
Overall, diethyl ether is a relatively inert compound that is resistant to nucleophilic attack by hydroxyl ions, making it a useful solvent in many chemical reactions.
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Which one of the following compounds is resistant to nucleophilic attack by hydroxyl ions?a)Methyl acetateb)Acetonitrile [1998]c)Diethyl etherd)AcetamideCorrect answer is option 'C'. Can you explain this answer?
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