Experiment Six - Pre-Lab

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Feb 20, 2024

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Experiment Six – Identification of an Unknown Aldehyde or Ketone XXXXX University of South Carolina CHEM 332L-016 TA: March 14, 2023
Purpose/Objective The purpose of this lab is to prepare a semicarbazone derivative and a 2,4- dinitrophenylhydrazone (2,4-DNP) derivative of unknown aldehydes or ketones, recrystallize them, and determine their melting point. Through this process, the identity of the unknown substances can be determined. Introduction Carbonyl compounds are sp 2 hybridized and trigonal planar with bond angles of 120°. A carbonyl group is relatively uncrowded, but as the alkyl groups around the carbonyl carbon increases, the reactivity of the carbonyl compound decreases. Since oxygen is more electronegative than carbon, oxygen has a greater share of the double bond’s electrons making the carbonyl group polar. Meaning the carbon is an electrophile, electron-deficient, which is subject to a nucleophilic attack. Reactions of carbonyl compounds are mostly acid catalyzed. Through this reaction, the acid will protonate the electronegative oxygen to form a carbocation, which is more susceptible to nucleophilic addition. All reactions are reversible because either of the two atoms with a lone pair attached to the tetrahedral carbon can be protonated and therefore eliminated. The reactions can be acid catalyzed with a controlled pH of 4.5. Derivatives are able to provide a solution by creating a solid for analysis and the solid derivative should be safe, easy to make, has a sharp melting point, and should be stable to hydrolysis. Imines, where the nitrogen atom carries an electronegative group that has a lone pair of electrons, are usually stable. This is due to the electronegative substituent that can participate in the delocalization of the imine double bond. The delocalization decreases the small positive charge on the carbon atom of the imine bond makes it less susceptible to nucleophilic attack. 2,4-
dinitrophenylhydrazine dissolved in EtOH/H 3 PO 4 will form a solid 2,4-dinitrophenylhydrazone when an aldehyde or ketone is reacted with it. Reaction Schemes/Structures 2,4-DNP Semicarbazide hydrochloride Reagents Name, Structure, MW (g/mol) Melting °C Boiling °C Density g/mL Properties 2,4-DNP Derivative (MP) Semicarb Derivative (MP) Benzaldehyde C 7 H 6 O 106.12 -26 178- 179 1.045 Flammable liquid; Cherry- like scent 237 °C 216 °C 3-Heptanone C 7 H 14 O 114.18 -39 147 0.818 Colorless liquid with a mild fruity odor; slightly soluble 81 °C 101 °C Acetophenone C 8 H 8 O 120.15 19.6 202 1.03 Colorless liquid but solid at lower temperatures 238 °C 198 °C Diethyl ketone C 5 H 10 O 86.1334 -42 101 0.814 Flammable liquid 156 °C 138 °C Cyclohexanon e -47 155 0.947 Flammable liquid oily, white to slightly yellow liquid with a peppermint-like 162 °C 166 °C
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