EXPERIMENT 6 Reactions o Carbonyl Compounds Qualitative 实验6反应的羰基化合物的定性.docVIP

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EXPERIMENT 6 Reactions o Carbonyl Compounds Qualitative 实验6反应的羰基化合物的定性.doc

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EXPERIMENT 6 Reactions o Carbonyl Compounds Qualitative 实验6反应的羰基化合物的定性

EXPERIMENT 6: Reactions of Carbonyl Compounds: Qualitative Reactions of Aldehydes and Ketones. Relevant sections in the text: Fox Whitesell, 3rd Ed. Sec. 13.1 (pg. 643-644) Reference??? General Concepts The carbonyl group (C=O), found in aldehydes, ketones, and esters is a very important functional group that is involved in several common reactions. This particular functionality is unique because of the polarization (dipolar resonance) between the carbon-oxygen ( bond. Due to the resonance of the C-O bond, there are a variety of reactions where the electrophilic carbon is attacked by nucleophiles (Lewis bases) and the oxygen reacts with corresponding electrophiles (Lewis acids). The result of the reaction is the addition of a Nu-E to the ( bond of the carbonyl group. The two most common mechanisms are outlined below, although they may vary based on the reagent and reaction conditions. Carbonyl groups can also increase the acidity of (–hydrogen atoms (hydrogens on carbons directly attached to the carbonyl), which allows the (-carbon to become nucleophilic. This may be achieved through a deprotonation reaction, forming an enolate ion (Eq.6.3), or by keto-enol equilibration (tautomerization) to form the enol (Eq. 6.4). These enolates and enols then react (at the (-carbon) with electrophiles, resulting in a substitution reaction between the (–hydrogen and the electrophile. The carbonyl groups in both aldehydes and ketones will be examined in this experiment. Although the two groups often react similarly, aldehydes commonly react faster than ketones (with the same reagent) due to less steric hindrance at the carbonyl group. Aldehydes are also more easily oxidized than ketones. You will examine the similarities and differences between ketones and aldehydes and then use those skills to accurately identify an unknown compound containing a carbonyl group. Experimental Procedure *Hazards*: Always work in the fumehood. The aldehydes and ketones in this