1-Bromopropane is heated with silver nitrite, AgNO2, in ether. The major product and its explanation are

CH3CH2CH2NO2; the Ag-N bond is largely covalent, so the nitrogen lone pair attacks the carbon

CH3CH2CH2NO2; silver ion makes the solvent protic and favours attack through nitrogen

CH3CH2CH2NO2; the Ag-N bond is largely covalent, so the nitrogen lone pair attacks the carbon

CH3CH2CH2-O-N=O; silver nitrite is ionic, so the more electronegative oxygen is the better nucleophile

CH3CH2CH2-O-N=O; the Ag-O bond is largely covalent, so oxygen attacks the carbon

MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / SN1 vs SN2: substrate, nucleophile, solvent, leaving group

JEE Main levelSingle correct optionDifficulty 2 of 3o3081

1-Bromopropane is heated with silver nitrite, $AgNO X_{2}$ , in ether. The major product and its explanation are

A $CH X_{3} CH X_{2} CH X_{2} NO X_{2}$ ; silver ion makes the solvent protic and favours attack through nitrogen
B $CH X_{3} CH X_{2} CH X_{2} NO X_{2}$ ; the Ag-N bond is largely covalent, so the nitrogen lone pair attacks the carbon
C $CH X_{3} CH X_{2} CH X_{2} - O - N = O$ ; silver nitrite is ionic, so the more electronegative oxygen is the better nucleophile
D $CH X_{3} CH X_{2} CH X_{2} - O - N = O$ ; the Ag-O bond is largely covalent, so oxygen attacks the carbon

Answer: B

Nitrite is an ambident nucleophile (N or O). Silver nitrite is covalent with the silver bonded to oxygen, which leaves the nitrogen lone pair free to attack carbon in SN2, giving the nitroalkane. This is the textbook contrast with free ionic nitrite.

Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN1 vs SN2: substrate, nucleophile, solvent, leaving group

Previous questionNext question

1-Bromopropane is heated with silver nitrite, AgNOX2​, in ether. The major product and its explanation are

Answer: B

More questions on SN1 vs SN2: substrate, nucleophile, solvent, leaving group

1-Bromopropane is heated with silver nitrite, $AgNO X_{2}$ , in ether. The major product and its explanation are