What is the stereochemical outcome of an SN2 substitution at an asymmetric sp3 carbon stereocenter?
Answer and explanation
Correct answer: C. Complete inversion of configuration (Walden inversion)
Because the nucleophile in an SN2 reaction must attack the carbon atom from the side directly opposite the leaving group (backside attack, 180° trajectory), the three non-reacting groups are inverted like an umbrella in a gale, resulting in complete inversion of configuration (Walden inversion).
Practise more Organic Reaction Mechanisms, Stereochemistry, and Biomolecules.
Free questions with an explanation for every one, and full timed Toelatingsexamen Arts & Tandarts België (Medical & Dental Entrance Exam) mock tests.
More Organic Reaction Mechanisms, Stereochemistry, and Biomolecules questions
- Which reaction conditions favor an SN2 nucleophilic substitution mechanism over an SN1 mechanism?
- According to Zaitsev's rule, what is the major alkene product obtained from the acid-catalyzed dehydration of 2-butanol?
- What is the major organic product formed when propene reacts with hydrogen bromide (HBr) in the absence of peroxides?
- According to Hückel's rule, which criteria must a monocyclic planar conjugated ring system satisfy to be classified as aromatic?
- Which substituent on a benzene ring acts as a deactivating, meta-directing group in electrophilic aromatic substitution?
- What chemical functional group is formed when an aldehyde reacts reversibly with one equivalent of an alcohol in the presence of an acid cat…