The observations for the regiochemical and the stereochemical outcome for the formation of the product given have to be identified. 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.

Question

Want to see the full answer?

Answer 1

Question

Chapter 13, Problem 75CP

Interpretation Introduction

Interpretation:

The observations for the regiochemical and the stereochemical outcome for the formation of the product given have to be identified.

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Consider the following data for phosphorus: g atomic mass 30.974 mol electronegativity 2.19 kJ electron affinity 72. mol kJ ionization energy 1011.8 mol kJ heat of fusion 0.64 mol You may find additional useful data in the ALEKS Data tab. Does the following reaction absorb or release energy? 2+ + (1) P (g) + e → P (g) Is it possible to calculate the amount of energy absorbed or released by reaction (1) using only the data above? If you answered yes to the previous question, enter the amount of energy absorbed or released by reaction (1): Does the following reaction absorb or release energy? 00 release absorb Can't be decided with the data given. yes no ☐ kJ/mol (²) P* (8) + + + e →>> P (g) Is it possible to calculate the amount of energy absorbed or released by reaction (2) using only the data above? If you answered yes to the previous question, enter the amount of energy absorbed or released by reaction (2): ☐ release absorb Can't be decided with the data given. yes no kJ/mol а

The number of hydrogens in an alkyne that has a main chain of 14carbons to which are attached a cyclobutyl ring, a benzene ring, an–OH group, and a Br is A. 34; B. 35; C. 36; D. 24; E. 43

Hello! I have a 500 Hz H-NMR for 1,5-bis-(4-methoxyphenyl)-penta-1,4-dien-3-one. I need to label the signals with the corresponding H's. Then, find out if the two alkenes are cis or trans by calculating the J values. I believe that I have the H-NMR labeled correctly, but not sure if I got the J values correct to determine if the two alkenes in the compound will make the compound cis or trans.