Q20E - Organic Chemistry (Mcmurry)

Question

The following model is a representation of acetaminophen, a pain reliever sold in drugstores under a variety of names, including Tylenol. Identify the hybridization of each carbon atom in acetaminophen, and tell which atoms have lone pairs of electrons (gray 5 C, red 5 O, blue 5 N, ivory 5 H).

Step-by-Step Solution

Answer

Structure of acetaminophen

Step 1: Acetaminophen

Commonly called paracetamol is used to treat fever and mild pain. Its molecular formula is ${\mathbf{C}}_8{\mathbf{H}}_9{\mathbf{NO}}_2$. Its molecular mass is 151.16 g/mol.

Step 2: Hybridization and lone pair

The carbon in $-{\mathrm{CH}}_3$ group is ${\mathrm{sp}}^3$hybridized and all other carbon atoms are ${\mathrm{sp}}^2$ hybridized. Oxygen and nitrogen atoms contain lone pair of electrons as shown:

Structure of acetaminophen