(a)
Interpretation: The plausible mechanism for each of the transformations to be predicted.
Concept Introduction:
Ring-opening of
Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).
Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.
Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.
(b)
Interpretation: The plausible mechanism for each of the transformations to be predicted.
Concept Introduction:
Ring-opening of epoxide: The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile result in the ring-opening reaction.
Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).
Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.
Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.
(c)
Interpretation: The plausible mechanism for each of the transformations to be predicted.
Concept Introduction:
Ring-opening of epoxide: The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile result in the ring-opening reaction.
Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).
Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.
Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.
(d)
Interpretation: The plausible mechanism for each of the transformations to be predicted.
Concept Introduction:
Ring-opening of epoxide: The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile result in the ring-opening reaction.
Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).
Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.
Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.
(e)
Interpretation: The plausible mechanism for each of the transformations to be predicted.
Concept Introduction:
Ring-opening of epoxide: The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile result in the ring-opening reaction.
Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).
Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.
Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.
(f)
Interpretation: The plausible mechanism for each of the transformations to be predicted.
Concept Introduction:
Ring-opening of epoxide: The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile result in the ring-opening reaction.
Acid-catalyzed ring-opening of epoxide: The epoxide ring is protonated and the nucleophile attack depends on the electronic or steric effect (nature of epoxide).
Regiochemistry: when the epoxide is unsymmetrical, the nucleophile attack at the more substituted position of the protonated epoxide ring.
Stereochemistry: when the nucleophile attack takes place at chiral center, an inversion of configuration is obtained.
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Chapter 13 Solutions
ORGANIC CHEMISTRY-PRINT COMPANION (LL)
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