The increasing order of nucleophilicity of the following nucleophiles is : (a) ${CH_3CO^{\ominus}_2}$ (b) ${H_2O} $ (c) ${CH_3SO^{\ominus}_3}$ (d) ${O^{\ominus}H}$

Question

Given below are two statements:
Statement I: Phenol on treatment with $ \mathrm{CHCl_3/aq.\ KOH} $ under refluxing condition, followed by acidification produces p-hydroxy benzaldehyde as the major product and o-hydroxy benzaldehyde as the minor product.
Statement II: The mixture of p-hydroxybenzaldehyde and o-hydroxybenzaldehyde can be easily separated through steam distillation.
In the light of the above statements, choose the correct answer from the options given below

Answer 1

To determine the increasing order of nucleophilicity among the given nucleophiles, we need to understand the concept of nucleophilicity. Nucleophilicity refers to the ability of a species to donate an electron pair to an electrophile, and it is influenced by factors such as charge, electronegativity, steric hindrance, and the solvent it is in. Here are the nucleophiles being compared:

CH_3CO^{\ominus}_2 (acetate ion)
H_2O (water)
CH_3SO^{\ominus}_3 (mesylate ion)
O^{\ominus}H (hydroxide ion)

Let's evaluate each of these:

H_2O (Water): Water is a weak nucleophile because it is neutral and has no negative charge to readily donate electrons.
CH_3SO^{\ominus}_3 (Mesylate Ion): The mesylate ion is a stronger nucleophile than water due to its negative charge, but it is stabilized by resonance, thus slightly reducing its nucleophilicity.
CH_3CO^{\ominus}_2 (Acetate Ion): This ion also has a negative charge and is stabilized by resonance within the acetate structure, making it a moderate nucleophile, stronger than the mesylate ion.
O^{\ominus}H (Hydroxide Ion): Hydroxide is a strong nucleophile because of the negative charge concentrated on a non-resonance stabilized oxygen atom, making it one of the strongest among the given species.

Therefore, the increasing order of nucleophilicity is:

(b) < (c) < (a) < (d)

This order is derived from considering both the negative charge and the effect of resonance, as well as the basicity of the nucleophiles, with hydroxide being the strongest nucleophile out of the four.

Answer 2

To determine the increasing order of nucleophilicity among the given nucleophiles, we need to understand the concept of nucleophilicity. Nucleophilicity refers to the ability of a species to donate an electron pair to an electrophile, and it is influenced by factors such as charge, electronegativity, steric hindrance, and the solvent it is in. Here are the nucleophiles being compared:

CH_3CO^{\ominus}_2 (acetate ion)
H_2O (water)
CH_3SO^{\ominus}_3 (mesylate ion)
O^{\ominus}H (hydroxide ion)

Let's evaluate each of these:

H_2O (Water): Water is a weak nucleophile because it is neutral and has no negative charge to readily donate electrons.
CH_3SO^{\ominus}_3 (Mesylate Ion): The mesylate ion is a stronger nucleophile than water due to its negative charge, but it is stabilized by resonance, thus slightly reducing its nucleophilicity.
CH_3CO^{\ominus}_2 (Acetate Ion): This ion also has a negative charge and is stabilized by resonance within the acetate structure, making it a moderate nucleophile, stronger than the mesylate ion.
O^{\ominus}H (Hydroxide Ion): Hydroxide is a strong nucleophile because of the negative charge concentrated on a non-resonance stabilized oxygen atom, making it one of the strongest among the given species.

Therefore, the increasing order of nucleophilicity is:

(b) < (c) < (a) < (d)

This order is derived from considering both the negative charge and the effect of resonance, as well as the basicity of the nucleophiles, with hydroxide being the strongest nucleophile out of the four.

The increasing order of nucleophilicity of the following nucleophiles is : (a) ${CH_3CO^{\ominus}_2}$ (b) ${H_2O} $ (c) ${CH_3SO^{\ominus}_3}$ (d) ${O^{\ominus}H}$

The Correct Option is A

Solution and Explanation

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