Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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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, 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, 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, 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, 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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