Module 7, 'Nucleophilic addition to carbonyl groups', discusses the addition of nucleophiles to aldehydes and ketones from the basics to details of reaction mechanisms. These reactions are critical to the biochemistry of sugars and starches that form the basis of forage crops! The material presented should allow prediction of reaction mechanism from reactants. A new reaction mechanism, nucleophilic addition to carbonyl electrophiles, is introduced, and the SN1 mechanism returns! Module 7 references chapter 10 of Soderberg found in volume II.
1. Nucleophilic addition of alcohols to the carbonyl group of aldehydes and ketones produces
hemiacetals and hemiketals; addition of a second alcohol produces acetals and ketals.
2. This nucleophilic addition reaction plays a major role in carbohydrate chemistry.
Module 7 slide sets: Nucleophilic addition to carbonyls
(Click on the links below to download each slide set for the lecture.)
Introduction: Panda Power
7.1: Nucleophilic additions to aldehydes and ketones: an overview
7.1A: Remember aldehydes and ketones?
7.1B: Nucleophilic addition
7.1C: Stereochemistry of nucleophilic addition
7.2: Hemiacetals, hemiketals and hydrates
7.2B: Sugars as intramolecular hemiacetals and hemiketals
7.3: Acetals and ketals
7.3B: Glycosidic bond formation
7.3C: Glycosidic bond hydrolysis
7.4: N-glycosidic bonds
7.5: Imines and iminium ions
7.6: A look ahead: addition of carbon and hydride nucleophiles to carbonyls
Resources for students:
> Module 7 lecture outline (PDF)
> Module 7 lecture with instructor's notes (PDF)
> Module 7 key concepts
> Module 7 practice problems
> Practice problems KEY
Video tutorials for Module 7:
> Homework set 7