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Concept explainers
(a)
Interpretation:
The major product of the given reaction should be drawn.
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.
Base catalyzed ring opening of epoxide:
The nucleophile will attack at the less substituted position under basic conditions and then the alkoxide ion gets proton from alcohol which form the product.
(b)
Interpretation:
The major product of the given reaction should be drawn.
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.
Base catalyzed ring opening of epoxide:
The nucleophile will attack at the less substituted position under basic conditions and then the alkoxide ion gets proton from alcohol which form the product.
(c)
Interpretation:
The major product of the given reaction should be drawn.
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.
Base catalyzed ring opening of epoxide:
The nucleophile will attack at the less substituted position under basic conditions and then the alkoxide ion gets proton from alcohol which form the product.
(d)
Interpretation:
The major product of the given reaction should be drawn.
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.
Base catalyzed ring opening of epoxide:
The nucleophile will attack at the less substituted position under basic conditions and then the alkoxide ion gets proton from alcohol which form the product.
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Chapter 9 Solutions
Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
- Draw the major product of the following reaction. + AICI3 ?arrow_forwardDraw the major organic product from the following reaction.arrow_forwardPredict the major product for the following reaction sequence. N-H (two equivalents) ? Modify the given structure of the starting material to draw the major product.arrow_forward
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- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
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