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...
Related questions
Question
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 2 images
Recommended textbooks for you
Chemistry for Today: General, Organic, and Bioche…
Chemistry
ISBN:
9781305960060
Author:
Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:
Cengage Learning
Chemistry for Today: General, Organic, and Bioche…
Chemistry
ISBN:
9781305960060
Author:
Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:
Cengage Learning