CHEM 302 S09 CA7 key

CHEM 302 S09 CA7 key - CHEM302, Spring 2009 Dr. Ruder 1...

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CHEM302, Spring 2009 Dr. Ruder 1 Class Activity 7 Reactions of Carboxylic Acid Derivatives Model 1 : Carboxylic Acid Derivative C O R Y carboxylic acid derivative Questions: 1. (a). Draw two additional resonance forms for the carboxylic acid derivative shown in Model 1. C O R Y C O R Y C O R Y (b). Draw the resonance forms for a ketone. How do the resonance forms of a ketone differ from the resonance forms for the carboxylic acid derivative? The resonance forms for the carboxylic acid derivatives have an additional resonance form because the Y group has a lone pair of electrons. C O R R C O R R (c). Which atom in the carboxylic acid derivative would act as the electrophile? The carbonyl carbon. (d). Would a Y group that donates or accepts electrons make the acid derivative a better electrophile? Explain. If the Y group is electron withdrawing that will polarize the C-X bond making the carbon more positive. (e). Would a Y group that donates or accepts electrons make the acid derivative a worse electrophile? Explain. If the Y group is electron donating electrons can be donated towards the carbonyl, making the carbon more electron rich. 2 . Identify the carboxylic acid derivatives by circling the Y group in each compound. Put an X through any compounds that are not carboxylic acid derivatives. C O R OCH 3 C O R Cl C O R CH 3 C O R NH 2 C O R O C R O This is the general structure of a carboxylic acid derivative, where Y is any atom that contains at least one lone pair of electrons.
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CHEM 302 S09 CA7 key - CHEM302, Spring 2009 Dr. Ruder 1...

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