The reagents for the given transformations to be identified. Concept Introduction : Ring-opening of epoxide : The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile. Thus the nucleophile attack at the less substituted position (due to steric effect) leads to the ring-opening. 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.

Question

Arrange the solutions in order of increasing acidity. (Note that K (HF) = 6.8 x 10 and K (NH3) = 1.8 × 10-5) Rank solutions from least acidity to greatest acidity. To rank items as equivalent, overlap them. ▸ View Available Hint(s) Least acidity NH&F NaBr NaOH NH,Br NaCIO Reset Greatest acidity

Answer 1

Question

Chapter 13, Problem 44PP

Interpretation Introduction

Interpretation: The reagents for the given transformations to be identified.

Concept Introduction:

Ring-opening of epoxide: The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile. Thus the nucleophile attack at the less substituted position (due to steric effect) leads to the ring-opening.

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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