MediumChemistryHigh School (11–12)Organic Compounds with Functional Groups › Aldehydes, Ketones and Carboxylic AcidsNumerical

1.00 g of acetophenone (120.15 g/mol) is warmed with excess iodine and sodium hydroxide…

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$1.00\ \text{g}$ of acetophenone ( $120.15\ \text{g/mol}$ ) is warmed with excess iodine and sodium hydroxide. The equation is $\text{C}_6\text{H}_5\text{COCH}_3 + 3\,\text{I}_2 + 4\,\text{NaOH} \to \text{C}_6\text{H}_5\text{COONa} + \text{CHI}_3 + 3\,\text{NaI} + 3\,\text{H}_2\text{O}$ . Find the amount of acetophenone, the mass of iodoform ( $393.73\ \text{g/mol}$ ) at a $100\ \%$ yield, and the number of carbon atoms in the organic acid that forms after acidification.

Need a reminder? The key ideaShow

Wolff-Kishner and Clemmensen turn C=O into CH $_2$ (base and acid). Perkin: ArCHO, (CH $_3$ CO) $_2$ O and CH $_3$ COONa at 453 K give ArCH=CHCOOH. Haloform: CH $_3$ CO- with 3 X $_2$ and 4 NaOH gives CHX $_3$ and the carboxylate with one carbon fewer. A crossed aldol with an aldehyde that has no alpha hydrogen is a Claisen-Schmidt reaction. For a gas, $V = nRT/P$ with $R = 8.314$ kPa L/(mol K).

The worked solution

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