Organic Chemistry, Loose-leaf Version
Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 3, Problem 3.20P

Assign priorities to the groups in each set.

  1. (a) —H —CH3 —OH —CH2OH
  2. (b) —CH2CH=CH2 —CH=CH2 —CH3 —CH2COOH
  3. (c) —CH3 —H —COO—NH3+
  4. (d) —CH3 —CH2SH —NH3+ —CHO

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Priorities to the given groups has to be assigned.

Concept Introduction:

Priority rules:

  • Priorities based on atomic number

-H,-CH3,-NH2,-OH,-SH,-Cl,-Br,-IIncreasingpriority

  • When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center

-CH2H,-CH2CH3,-CH2NH2,-CH2OH,-CH2ClIncreasingpriority

  • Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.

For example,

Organic Chemistry, Loose-leaf Version, Chapter 3, Problem 3.20P , additional homework tip  1

  • Priority assignment is made at the first point of difference between groups (should not be based on the larger group).

Explanation of Solution

Given groups,

-H,-CH3,-OHand-CH2OH

Assign priorities to the given groups based on the priority rules,

-OH>-CH2OH>-CH3>-H

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Priorities to the given groups has to be assigned.

Concept Introduction:

Priority rules:

  • Priorities based on atomic number

-H,-CH3,-NH2,-OH,-SH,-Cl,-Br,-IIncreasingpriority

  • When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center

-CH2H,-CH2CH3,-CH2NH2,-CH2OH,-CH2ClIncreasingpriority

  • Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.

For example,

Organic Chemistry, Loose-leaf Version, Chapter 3, Problem 3.20P , additional homework tip  2

  • Priority assignment is made at the first point of difference between groups (should not be based on the larger group).

Explanation of Solution

Given groups,

-CH2CH=CH2,-CH=CH2,-CH3and-CH2COOH

Assign priorities to the given groups based on the priority rules,

-CH=CH2>-CH2COOH>-CH2CH=CH2>-CH3

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Priorities to the given groups has to be assigned.

Concept Introduction:

Priority rules:

  • Priorities based on atomic number

-H,-CH3,-NH2,-OH,-SH,-Cl,-Br,-IIncreasingpriority

  • When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center

-CH2H,-CH2CH3,-CH2NH2,-CH2OH,-CH2ClIncreasingpriority

  • Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.

For example,

Organic Chemistry, Loose-leaf Version, Chapter 3, Problem 3.20P , additional homework tip  3

  • Priority assignment is made at the first point of difference between groups (should not be based on the larger group).

Explanation of Solution

Given groups,

-H,-CH3,-COO-and-NH3+

Assign priorities to the given groups based on the priority rules,

-NH3+>-COO->-CH3>-H

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Priorities to the given groups has to be assigned.

Concept Introduction:

Priority rules:

  • Priorities based on atomic number

-H,-CH3,-NH2,-OH,-SH,-Cl,-Br,-IIncreasingpriority

  • When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center

-CH2H,-CH2CH3,-CH2NH2,-CH2OH,-CH2ClIncreasingpriority

  • Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.

For example,

Organic Chemistry, Loose-leaf Version, Chapter 3, Problem 3.20P , additional homework tip  4

  • Priority assignment is made at the first point of difference between groups (should not be based on the larger group).

Explanation of Solution

Given groups,

-CH3,-CH2SH,-NH3+and-CHO

Assign priorities to the given groups based on the priority rules,

-NH3+>-CH2SH>-CHO>-CH3

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Methyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Methyl isocyanate reacts with strong acids, such as sulfuric acid, to form a cation. Will this molecule undergo protonation more readily on its oxygen or nitrogen atom? In considering contributing structures to each hybrid, do not consider structures in which more than one atom has an incomplete octet

Chapter 3 Solutions

Organic Chemistry, Loose-leaf Version

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