Which of the following behaves both as a nucleophile and as an electrophile?(a) CH3C ≡ N(b) CH3OH(c) CH2 = CHCH3(d) CH3NH2
Question
Which of the following behaves both as a nucleophile and as an electrophile?(a) CH3C ≡ N(b) CH3OH(c) CH2 = CHCH3(d) CH3NH2
Solution 1
The compound that behaves both as a nucleophile and as an electrophile is (b) CH3OH.
Here's why:
A nucleophile is a species that donates an electron pair to an electrophile to form a chemical bond in a reaction. Electrophiles are species that accept an electron pair in order to form a chemical bond.
(a) CH3C ≡ N: This is an alkyne and it can act as a nucleophile but not as an electrophile.
(b) CH3OH: This is methanol. The oxygen in methanol has a lone pair of electrons, which can be donated, making it a good nucleophile. On the other hand, the hydrogen atoms in the -OH group can be removed as a proton (H+), leaving the oxygen atom with a negative charge. This allows it to accept an electron pair, making methanol also an electrophile.
(c) CH2 = CHCH3: This is an alkene and it can act as a nucleophile but not as an electrophile.
(d) CH3NH2: This is an amine and it can act as a nucleophile but not as an electrophile.
So, the correct answer is (b) CH3OH.
Solution 2
The compound that behaves both as a nucleophile and as an electrophile is (b) CH3OH.
Here's why:
A nucleophile is a species that donates an electron pair to an electrophile to form a chemical bond in a reaction. Electrophiles are species that accept an electron pair in order to form a chemical bond.
(a) CH3C ≡ N: This is a nitrile and it can act as a nucleophile but not as an electrophile.
(b) CH3OH: This is methanol and it can act as both a nucleophile and an electrophile. The oxygen in methanol has lone pairs of electrons, so it can donate electrons and act as a nucleophile. On the other hand, the hydrogen atoms in the -OH group are slightly acidic. When these hydrogens are removed as protons (H+), the remaining oxygen atom can accept a pair of electrons, allowing methanol to act as an electrophile.
(c) CH2 = CHCH3: This is propene and it can act as a nucleophile but not as an electrophile.
(d) CH3NH2: This is methylamine and it can act as a nucleophile but not as an electrophile.
So, the correct answer is (b) CH3OH.
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