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5.18 NH2 N=N (i) HCI, NaNO2 (ii) PHNME2 `CO2H CO2H `NM@2 Amines are good nucleophiles (nitrogen possesses a lone pair). Sodium nitrite under acidic conditions generates HONO, a source of 0-N*, which is a potent electrophile. The amine is the most nucleophilic site, although it is deactivated somewhat by the acid substituent at the o-position by a resonance delocalisation of the nitrogen lone pair. 0=N* is the only electrophile. The combination NaNO,/HCI generates HONO (nitrous acid), which is in equilibrium with N,03, a source of 0=N*. This reagent diazotises amine functional groups, converting NH2 to N,*. Na-ON=O NH2 N=N, 3 -NME2 8- 4. CO,H co,H NME2 8+ 2 NaONO 2 HCI 2 O=N-OH + H20

5.18 NH2 N=N (i) HCI, NaNO2 (ii) PHNME2 `CO2H CO2H `NM@2 Amines are good nucleophiles (nitrogen possesses a lone pair). Sodium nitrite under acidic conditions generates HONO, a source of 0-N*, which is a potent electrophile. The amine is the most nucleophilic site, although it is deactivated somewhat by the acid substituent at the o-position by a resonance delocalisation of the nitrogen lone pair. 0=N* is the only electrophile. The combination NaNO,/HCI generates HONO (nitrous acid), which is in equilibrium with N,03, a source of 0=N*. This reagent diazotises amine functional groups, converting NH2 to N,*. Na-ON=O NH2 N=N, 3 -NME2 8- 4. CO,H co,H NME2 8+ 2 NaONO 2 HCI 2 O=N-OH + H20

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 30MP: The carbocation electrophile in a Friede1-Crafts reaction can be generated by an alternate means...
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5.18 NH2 N=N (1) HCI, NANO2 (ii) PHNM@2 CO2H CO2H `NM@2 Amines are good nucleophiles (nitrogen possesses a lone pair). Sodium nitrite under acidic conditions generates HONO, a source of 0=N*, which is a potent electrophile. The amine is the most nucleophilic site, although it is deactivated somewhat by the acid substituent at the o-position by a resonance delocalisation of the nitrogen lone pair. 0=N+ is the only electrophile. The combination NaNO2/HCl generates HONO (nitrous acid), which is in equilibrium with N,02, a source of 0=N*. This reagent diazotises amine functional groups, converting NH, to N,*. CI Na-ON=O 2 NH2 NEN, 3 3 CO2H -NM22 8- CO,H `NM22 5 2 NaONO + 2 HCI O=N-OH + H20
Transcribed Image Text:5.18 NH2 N=N (1) HCI, NANO2 (ii) PHNM@2 CO2H CO2H `NM@2 Amines are good nucleophiles (nitrogen possesses a lone pair). Sodium nitrite under acidic conditions generates HONO, a source of 0=N*, which is a potent electrophile. The amine is the most nucleophilic site, although it is deactivated somewhat by the acid substituent at the o-position by a resonance delocalisation of the nitrogen lone pair. 0=N+ is the only electrophile. The combination NaNO2/HCl generates HONO (nitrous acid), which is in equilibrium with N,02, a source of 0=N*. This reagent diazotises amine functional groups, converting NH, to N,*. CI Na-ON=O 2 NH2 NEN, 3 3 CO2H -NM22 8- CO,H `NM22 5 2 NaONO + 2 HCI O=N-OH + H20
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