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.
Want to see the full answer?
Check out a sample textbook solutionChapter 9 Solutions
EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
- Why won't most primary alkyl halides react in Friedel-Crafts alkylation reactions? O Primary alkyl halides undergo methyl shifts under the standard conditions of Friedel-Crafts alkylation reactions, making them unreactive. Primary alkyl halides create primary carbocations which are too high in energy and too readily undergo rearrangement. Primary alkyl halides do not form a sigma complex after a nucleophilic attack since they connect at the primary carbocation site. Primary alkyl halides as a reactant violates one of the three standard limitations to Friedel-Crafts alkylation reactions.arrow_forwardDraw the major organic product(s) of the following reaction. CH3OHarrow_forwardDraw the major product of the following reaction sequence. OH H2CrO4 HO NaBH4 H*/H20 ELOH он H3C* ноarrow_forward
- Draw the major product of the reactionarrow_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
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- 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