CHEMISTRY · Multi-part · AP · Chemistry · Compound Structure and Properties · Compound Structure and Properties
Problem
Nitrous acid, HONO, displays interesting bonding behavior that influences its acid strength.
Respond to the following prompts about HONO.
(a) Draw all valid resonance structures for neutral HONO, showing lone pairs and any formal charges.
(b) Identify the atoms that serve as electron donors and electron acceptors in each resonance contributor, and discuss how this electron movement affects the placement of positive and negative formal charges.
(c) Explain why delocalization onto an electronegative oxygen atom stabilizes certain resonance contributors more than delocalization onto nitrogen. Include a discussion of electronegativity and formal charge considerations.
(d) Describe how resonance in HONO contributes to its observed O–N bond length relative to the corresponding bond lengths in NH2OH (hydroxylamine) and H2O2 (hydrogen peroxide).