Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 7.8, Problem 15P
Interpretation Introduction

(a)

Interpretation: The stronger nucleophile out of Br and Cl in a polar protic solvent is to be identified.

Concept introduction: Solvent is required to dissolve the starting material in it. The substitution reaction involves polar starting reactant which is soluble in polar solvent. A solvent in which hydrogen atom is bonded to electronegative O or N atom is termed as polar protic solvent. The nucleophilicity of anion that has small size is higher than the anion that has larger size.

Interpretation Introduction

(b)

Interpretation: The stronger nucleophile out of Br and Cl in a polar aprotic solvent is to be identified.

Concept introduction: Solvent is required to dissolve the starting material in it. The substitution reaction involves polar starting reactant which is soluble in polar solvent. A solvent in which hydrogen atom is bonded to electronegative O or N atom is termed as polar protic solvent. However, in polar aprotic solvent, OH bond or NH is absent.

Interpretation Introduction

(c)

Interpretation: The stronger nucleophile out of HS and F in a polar protic solvent is to be identified.

Concept introduction: Solvent is required to dissolve the starting material in it. The substitution reaction involves polar starting reactant which is soluble in polar solvent. A solvent in which hydrogen atom is bonded to electronegative O or N atom is termed as polar protic solvent. The nucleophilicity of anion that has small size is higher than the anion that has larger size.

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Identify the stronger nucleophile in each pair of anions.a. Br- or Cl- in a polar protic solventb. HO- or Cl- in a polar aprotic solventc. HS- or F- in a polar protic solvent
Identify the stronger nucleophile in each pair of anions. a.Br− or Cl− in a polar protic solvent b.HO− or Cl− in a polar aprotic solvent c.HS− or F− in a polar protic solvent
Rank the nucleophiles in each group in order of increasing nucleophilicity. a.−OH, −NH2, H2O b.−OH, Br−, F− (polar aprotic solvent) c.H2O, −OH, CH3CO2−

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Organic Chemistry (6th Edition)

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