CHEMISTRY · Multi-part · AP · Chemistry · Compound Structure and Properties · Compound Structure and Properties
Problem
Acetamide, CH₃CONH₂, is an important solvent and intermediate in the pharmaceutical industry. A skeletal structure is provided below, with the three atoms of interest labeled.
H₃C—C(=O)—NH₂
C₁ O N
Respond to the prompts below.
(a) For each of the labeled atoms—carbonyl carbon (C₁), carbonyl oxygen (O), and amide nitrogen (N)—determine the hybridization state.
(b) Predict the molecular geometry at C₁ and give the approximate value of the H₃C–C₁–O bond angle.
(c) Compared with rotation about the C–C single bond in ethane, rotation about the C₁–N bond in acetamide is significantly restricted. Using your answers from part (a), explain the origin of this restricted rotation in terms of orbital overlap and bonding.