Addition–elimination: oximes, hydrazones
Aldehydes and Ketones · Chemistry
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Problem: What product is formed when acetone reacts with hydroxylamine, and what is eliminated during this process? Step 1: Identify the reactants. Acetone is a ketone with the formula CH3-C(=O)-CH3. Hydroxylamine is NH2OH. Step 2: Apply the addition step. The nitrogen of NH2OH attacks the carbonyl carbon of acetone, forming an unstable tetrahedral intermediate where carbon is bonded to OH and NH-OH. Step 3: Apply the elimination step. The oxygen from the carbonyl group of acetone combines with two hydrogens from the NH2 group of hydroxylamine to form one molecule of water (H2O), which is eliminated. Step 4: Form the final product. A carbon-nitrogen double bond (C=N) is created, connecting the acetone carbon to the =N-OH group. Step 5: Name the product. The resulting compound is acetone oxime, with the formula (CH3)2C=N-OH.