The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted. Concept Introduction : Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic. Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic. Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

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Answer 1

Question

Chapter 16.4, Problem 1PTS

(a)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(b)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(c)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(d)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(e)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

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Name the molecules & Identify any chiral center CH3CH2CH2CHCH₂CH₂CH₂CH₂ OH CH₂CHCH2CH3 Br CH3 CH3CHCH2CHCH2CH3 CH3

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electrons-pushing arrows for the following reaction or mechanistic step(s).

Answer 2

Question

Chapter 16.4, Problem 1PTS

(a)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(b)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(c)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(d)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(e)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

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Answer 3

Question

Chapter 16.4, Problem 1PTS

(a)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(b)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(c)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(d)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(e)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

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Answer 4

Question

Chapter 16.4, Problem 1PTS

(a)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(b)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(c)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(d)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(e)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

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Answer 5

Chapter 16.4, Problem 1PTS

(a)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(b)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(c)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(d)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

(e)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 6

Chapter 16.4, Problem 1PTS

(a)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 7

Chapter 16.4, Problem 1PTS

(a)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 8

(b)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 9

(b)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 10

(c)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 11

(c)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 12

(d)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 13

(d)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 14

(e)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 15

(e)

Interpretation Introduction

Interpretation: The given red protons are whether homotopic, Enantiotopic or Diastereotopic to be predicted.

Concept Introduction:

Homotopic: If the protons are interchangeable by rotational symmetry, then the protons are chemically equivalent and termed as homotopic.

Enantiotopic: If the protons are interchangeable by reflectional symmetry, then the protons are chemically equivalent and termed as Enantiotopic.

Diastereotopic: If the protons are not interchangeable by either of the symmetry operations, then the protons are Diastereotopic; the protons are not chemically equivalent if a chiral center present in the molecule.

Answer 16

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Answer 17

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Answer 18

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Answer 19

Ch. 16.4 - Prob. 1LTS Ch. 16.4 - Prob. 1PTS Ch. 16.4 - Prob. 2ATS Ch. 16.4 - Prob. 3ATS Ch. 16.4 - Prob. 2LTS Ch. 16.4 - Prob. 4PTS Ch. 16.4 - Prob. 5ATS Ch. 16.4 - Prob. 6ATS Ch. 16.5 - Prob. 3LTS Ch. 16.5 - Prob. 7PTS

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Chapter 16 Solutions