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Pearson's HSAB theory provides a simple explanation. When the reaction proceeds via $S_N1$, a hard acid (electrophile) is firstly generated (the carbocation) which interacts with the harder part of the nitrite anion an that's the oxygen-hard nucleophile. The $S_N2$ proceeds smoothly for the pair soft nucleophile-softnucleophile–soft electophile. 

In the given example the soft electrophilic carbon reacts with the soft center of the nitrite anion, and that's the nitrogen atom. In the former case, the silver coordinated to the oxygen definitely weakens its nucleophilicity. The formed carbocation has to be pretty hard and not so much stabilized by the solvent for the O-attack to be operative.

Pearson's HSAB theory provides a simple explanation. When the reaction proceeds via $S_N1$, a hard acid (electrophile) is firstly generated (the carbocation) which interacts with the harder part of the nitrite anion an that's the oxygen-hard nucleophile. The $S_N2$ proceeds smoothly for the pair soft nucleophile-soft electophile. In the given example the soft electrophilic carbon reacts with the soft center of the nitrite anion, and that's the nitrogen atom. In the former case, the silver coordinated to the oxygen definitely weakens its nucleophilicity. The formed carbocation has to be pretty hard and not so much stabilized by the solvent for the O-attack to be operative.

Pearson's HSAB theory provides a simple explanation. When the reaction proceeds via $S_N1$, a hard acid (electrophile) is firstly generated (the carbocation) which interacts with the harder part of the nitrite anion an that's the oxygen-hard nucleophile. The $S_N2$ proceeds smoothly for the pair soft nucleophile–soft electophile. 

In the given example the soft electrophilic carbon reacts with the soft center of the nitrite anion, and that's the nitrogen atom. In the former case, the silver coordinated to the oxygen definitely weakens its nucleophilicity. The formed carbocation has to be pretty hard and not so much stabilized by the solvent for the O-attack to be operative.

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Pearson's HSAB theory givesprovides a simple explanation. When the reaction proceeds via $S_N1$, a hard acid (electrophile) is firstly generated (the carbocation) which interacts with the harder part of the nitrite anion an that's the oxygen-hard nucleophile. The $S_N2$ proceeds smoothly for the pair soft nucleophile-soft electophile. In the given example the soft electrophilic carbon reacts with the soft center of the nitrite anion, and that's the nitrogen atom. In the former case, the silver coordinated to the oxygen definitely weakens its nucleophilicity. The formed carbocation has to be pretty hard and not so much stabilized by the solvent for the O-attack to be operative.

Pearson's HSAB theory gives a simple explanation. When the reaction proceeds via $S_N1$, a hard acid (electrophile) is firstly generated (the carbocation) which interacts with the harder part of the nitrite anion an that's the oxygen-hard nucleophile. The $S_N2$ proceeds smoothly for the pair soft nucleophile-soft electophile. In the given example the soft electrophilic carbon reacts with the soft center of the nitrite anion, and that's the nitrogen atom. In the former case, the silver coordinated to the oxygen definitely weakens its nucleophilicity. The formed carbocation has to be pretty hard and not so much stabilized by the solvent for the O-attack to be operative.

Pearson's HSAB theory provides a simple explanation. When the reaction proceeds via $S_N1$, a hard acid (electrophile) is firstly generated (the carbocation) which interacts with the harder part of the nitrite anion an that's the oxygen-hard nucleophile. The $S_N2$ proceeds smoothly for the pair soft nucleophile-soft electophile. In the given example the soft electrophilic carbon reacts with the soft center of the nitrite anion, and that's the nitrogen atom. In the former case, the silver coordinated to the oxygen definitely weakens its nucleophilicity. The formed carbocation has to be pretty hard and not so much stabilized by the solvent for the O-attack to be operative.

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Pearson's HSAB theoryHSAB theory gives a simple explanation. When the reaction proceeds via $S_N1$, a hard acid (electrophile) is firstly generated (the carbocation) which interacts with the harder part of the nitrite anion an that's the oxygen-hard nucleophile. The $S_N2$ proceeds smoothly for the pair soft nucleophile-soft electophile. In the given example the soft electrophilic carbon reacts with the soft center of the nitrite anion, and that's the nitrogen atom. In the former case, the silver coordinated to the oxygen definitely weakens its nucleophilicity. The formed carbocation has to be pretty hard and not so much stabilized by the solvent for the O-attack to be operative.

Pearson's HSAB theory gives a simple explanation. When the reaction proceeds via $S_N1$, a hard acid (electrophile) is firstly generated (the carbocation) which interacts with the harder part of the nitrite anion an that's the oxygen-hard nucleophile. The $S_N2$ proceeds smoothly for the pair soft nucleophile-soft electophile. In the given example the soft electrophilic carbon reacts with the soft center of the nitrite anion, and that's the nitrogen atom. In the former case, the silver coordinated to the oxygen definitely weakens its nucleophilicity. The formed carbocation has to be pretty hard and not so much stabilized by the solvent for the O-attack to be operative.

Pearson's HSAB theory gives a simple explanation. When the reaction proceeds via $S_N1$, a hard acid (electrophile) is firstly generated (the carbocation) which interacts with the harder part of the nitrite anion an that's the oxygen-hard nucleophile. The $S_N2$ proceeds smoothly for the pair soft nucleophile-soft electophile. In the given example the soft electrophilic carbon reacts with the soft center of the nitrite anion, and that's the nitrogen atom. In the former case, the silver coordinated to the oxygen definitely weakens its nucleophilicity. The formed carbocation has to be pretty hard and not so much stabilized by the solvent for the O-attack to be operative.

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