As we have seen in this chapter, carbon-carbon double bonds are electron-rich regions that are attacked by electrophiles (e.g., HBr); they are not attacked by nucleophiles (e.g, diethylamine). electrophilic addition HBr + Br (a racemic mixture) Et,NH + No reaction Diethylamine (a nucleophile) However, when the carbon-carbon double bond has a carbonyl group adjacent to it, the double bond reacts readily with nucleophiles by nucleophilic addition nucleophilic addition Et,NH + Et,N Diethylamine (a nucleophile) Account for the fact that nucleophiles add to a carbon-carbon double bond adjacent to a carbonyl group and account for the regiochemistry of the reaction.

As we have seen in this chapter, carbon-carbon double bonds are electron-rich regions that are attacked by electrophiles (e.g., HBr); they are not attacked by nucleophiles (e.g, diethylamine). electrophilic addition HBr + Br (a racemic mixture) Et,NH + No reaction Diethylamine (a nucleophile) However, when the carbon-carbon double bond has a carbonyl group adjacent to it, the double bond reacts readily with nucleophiles by nucleophilic addition nucleophilic addition Et,NH + Et,N Diethylamine (a nucleophile) Account for the fact that nucleophiles add to a carbon-carbon double bond adjacent to a carbonyl group and account for the regiochemistry of the reaction.

Chemistry for Today: General, Organic, and Biochemistry

9th Edition

ISBN:9781305960060

Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Chapter14: Aldehydes And Ketones

Section: Chapter Questions

Problem 14.55E: The addition of water to aldehydes and ketones occurs rapidly, although it is not thermodynamically...

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