Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 5, Problem 5.42P
Interpretation Introduction

(a)

Interpretation:

The number of chiral centers in the given molecule is to be identified and labeled with an asterisk.

Concept introduction:

A chiral center is a tetrahedral stereocenter. The atom at the chiral center must be sp3 hybridized and bonded to four different atoms or groups. Carbon and nitrogen are both capable of forming four bonds; therefore, they can be chiral centers if bonded to four different atoms or groups.

Expert Solution
Check Mark

Answer to Problem 5.42P

There are four chiral centers in the given molecule marked with asterisk (*):

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  1

Explanation of Solution

Structure of the given molecule is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  2

Expanding this line drawing to show the terminal carbons and adding hydrogen atoms at the remaining carbon atoms, the structure will look like

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  3

The terminal carbon atoms C1 and C6 are bonded to three hydrogen atoms. Therefore, they are not chiral centers.

C2 is bonded to the four groups, CH3, H, OH, and C4H9O3.

C3 is bonded to the four groups C2H5O, H, OH, and C3H7O2.

C4 is bonded to the four groups C2H5O, H, OH, and C3H7O2.

C5 is bonded to the four groups CH3, H, OH, and C4H9O3.

These four carbon atoms are bonded to four different groups and are chiral.

Therefore, there are four carbon atoms C2, C3, C4, and C5 are chiral centers

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  4

Conclusion

A carbon or a nitrogen atom is a chiral center if it is bonded to four different atoms or groups.

Interpretation Introduction

(b)

Interpretation:

The number of chiral centers in the given molecule is to be identified and labeled.

Concept introduction:

A chiral center is a tetrahedral stereocenter. The atom at the chiral center must be sp3 hybridized and bonded to four different atoms or groups. Carbon and nitrogen are both capable of forming four bonds; therefore, they can be chiral centers if bonded to four different atoms or groups.

Expert Solution
Check Mark

Answer to Problem 5.42P

The given molecule has two chiral centers labeled with an asterisk as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  5

Explanation of Solution

The line drawing of the given molecule is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  6

Expanding this line drawing to show the terminal carbons and adding hydrogen atoms at the remaining carbon atoms, the structure will look like

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  7

Both C1 and C6 are bonded to three hydrogens each. Therefore, they are not chiral centers.

C2 and C5 also are not chiral centers as two of the groups bonded to them are identical. Each one is bonded to two CH3.

C3 and C4 are bonded to four different groups C3H7, H, CH3, and C4H11.

Therefore, these two carbon atoms are chiral centers

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  8

Conclusion

A carbon or a nitrogen atom is a chiral center if it is bonded to four different atoms or groups.

Interpretation Introduction

(c)

Interpretation:

The number of chiral centers in the given molecule is to be identified and labeled.

Concept introduction:

A chiral center is a tetrahedral stereocenter. The atom at the chiral center must be sp3 hybridized and bonded to four different atoms or groups. Carbon and nitrogen are both capable of forming four bond; therefore, they can be chiral centers if bonded to four different atoms or groups.

Expert Solution
Check Mark

Answer to Problem 5.42P

The given molecule has no chiral centers.

Explanation of Solution

The line drawing of the molecule is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  9

A chiral center must be an sp3 hybridized atom to be bonded to four different groups. The carbon atoms in the benzene ring are all sp2 hybridized, and therefore, cannot be chiral centers.

In the alkyl substituent on the benzene ring, the terminal carbon has three hydrogen atoms bonded to it. The remaining two carbon atoms in the chain have two hydrogen atoms bonded to them. Therefore, these carbon atoms are also not chiral centers.

Conclusion

A carbon or a nitrogen atom is a chiral center if it is bonded to four different atoms or groups.

Interpretation Introduction

(d)

Interpretation:

The number of chiral centers in the given molecule is to be identified and labeled.

Concept introduction:

A chiral center is a tetrahedral stereocenter. The atom at the chiral center must be sp3 hybridized and bonded to four different atoms or groups. Carbon and nitrogen are both capable of forming four bonds; therefore, they can be chiral centers if bonded to four different atoms or groups.

Expert Solution
Check Mark

Answer to Problem 5.42P

There is one chiral center in the given molecular ion:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  10

Explanation of Solution

Line drawing of the given molecular ion is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  11

The molecule consists of a ring made up of five carbon atoms and one oxygen atom, with a methyl substituent on the carbon next to O. Oxygen does not form four bonds, and therefore, it cannot be a chiral center.

The carbon that has a methyl group bonded to it is also bonded to another (ring) carbon, the oxygen atom, and a hydrogen atom – all four are different. Therefore, this carbon is a chiral center. The remaining four ring carbons are bonded to two hydrogen atoms, so they cannot be chiral centers.

Therefore, there is only one chiral center in this molecular ion:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  12

Conclusion

A carbon or a nitrogen atom is a chiral center if it is bonded to four different atoms or groups.

Interpretation Introduction

(e)

Interpretation:

The number of chiral centers in the given molecule is to be identified and labeled.

Concept introduction:

A chiral center is a tetrahedral stereocenter. The atom at the chiral center must be sp3 hybridized and bonded to four different atoms or groups. Carbon and nitrogen are both capable of forming four bonds; therefore, they can be chiral centers if bonded to four different atoms or groups.

Expert Solution
Check Mark

Answer to Problem 5.42P

There is one chiral center C3 in the given molecular ion

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  13

Explanation of Solution

The line drawing of the molecular ion is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  14

Adding in the terminal carbons as methyl groups and numbering the carbon chain as below helps in identifying which carbon atoms could be chiral centers:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  15

The four terminal carbon atoms are bonded to three hydrogen atoms each, and therefore cannot be chiral centers. C2 and the nitrogen atom are also not chiral centers since they are sp2 hybridized.

C4 is also not a chiral center as it has two hydrogen atoms bonded to it.

C3 is the only carbon atom that is bonded to four different groups C2H5, H, CH3, and a double bonded carbon.

Therefore, C3 is the only chiral center in the molecule.

Conclusion

A carbon or a nitrogen atom is a chiral center if it is bonded to four different atoms or groups.

Interpretation Introduction

(f)

Interpretation:

The number of chiral centers in the given molecule is to be identified and labeled.

Concept introduction:

A chiral center is a tetrahedral stereocenter. The atom at the chiral center must be sp3 hybridized and bonded to four different atoms or groups. Carbon and nitrogen are both capable of forming four bonds; therefore, they can be chiral centers if bonded to four different atoms or groups.

Expert Solution
Check Mark

Answer to Problem 5.42P

There are two chiral centers in the given molecular ion:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  16

Explanation of Solution

The line drawing of the given molecular ion is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  17

Adding in the terminal methyl groups gives the structure:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  18

The terminal carbon atoms have three hydrogen atoms bonded to them, so they cannot be chiral centers. The two double bonded carbon atoms also cannot be chiral centers as chirality requires the atoms to be sp3 hybridized.

The two remaining carbons in the alkenyl substituent on N have two hydrogen atoms bonded to each, and therefore cannot be chiral centers.

The ring carbon that is bonded to N is also bonded to three different groups, H, CH3, and CH2, Therefore, this carbon is a chiral center. The remaining three ring carbons are bonded to two hydrogens and cannot be chiral centers.

The nitrogen atom is sp3 hybridized, and bonded to four different groups; CH3,CH2,CH(CH3), and an sp2 carbon. Therefore, the nitrogen atom is also a chiral center.

Therefore, there are two chiral centers in this molecular ion:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  19

Conclusion

A carbon or a nitrogen atom is a chiral center if it is bonded to four different atoms or groups.

Interpretation Introduction

(g)

Interpretation:

The number of chiral centers in the given molecule is to be identified and labeled.

Concept introduction:

A chiral center is a tetrahedral stereocenter. The atom at the chiral center must be sp3 hybridized and bonded to four different atoms or groups. Carbon and nitrogen are both capable of forming four bonds; therefore, they can be chiral centers if bonded to four different atoms or groups.

Expert Solution
Check Mark

Answer to Problem 5.42P

There are no chiral centers in the given molecule.

Explanation of Solution

The line drawing of the molecule is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.42P , additional homework tip  20

Four of the six ring carbons are bonded to two hydrogen atoms each. Therefore, they cannot be chiral centers.

The remaining two ring carbons have two identical groups bonded to them. The symmetry of the ring means the two sides are identical. These two carbons are also not chiral carbons.

Therefore, this molecule has no chiral centers.

Conclusion

A carbon or a nitrogen atom is a chiral center if it is bonded to four different atoms or groups.

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Chapter 5 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Prob. 5.13PCh. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - Prob. 5.27PCh. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Prob. 5.34PCh. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Prob. 5.37PCh. 5 - Prob. 5.38PCh. 5 - Prob. 5.39PCh. 5 - Prob. 5.40PCh. 5 - Prob. 5.41PCh. 5 - Prob. 5.42PCh. 5 - Prob. 5.43PCh. 5 - Prob. 5.44PCh. 5 - Prob. 5.45PCh. 5 - Prob. 5.46PCh. 5 - Prob. 5.47PCh. 5 - Prob. 5.48PCh. 5 - Prob. 5.49PCh. 5 - Prob. 5.50PCh. 5 - Prob. 5.51PCh. 5 - Prob. 5.52PCh. 5 - Prob. 5.53PCh. 5 - Prob. 5.54PCh. 5 - Prob. 5.55PCh. 5 - Prob. 5.56PCh. 5 - Prob. 5.57PCh. 5 - Prob. 5.58PCh. 5 - Prob. 5.59PCh. 5 - Prob. 5.60PCh. 5 - Prob. 5.61PCh. 5 - Prob. 5.62PCh. 5 - Prob. 5.63PCh. 5 - Prob. 5.64PCh. 5 - Prob. 5.65PCh. 5 - Prob. 5.66PCh. 5 - Prob. 5.67PCh. 5 - Prob. 5.68PCh. 5 - Prob. 5.69PCh. 5 - Prob. 5.70PCh. 5 - Prob. 5.71PCh. 5 - Prob. 5.72PCh. 5 - Prob. 5.73PCh. 5 - Prob. 5.74PCh. 5 - Prob. 5.75PCh. 5 - Prob. 5.76PCh. 5 - Prob. 5.77PCh. 5 - Prob. 5.78PCh. 5 - Prob. 5.79PCh. 5 - Prob. 5.1YTCh. 5 - Prob. 5.2YTCh. 5 - Prob. 5.3YTCh. 5 - Prob. 5.4YTCh. 5 - Prob. 5.5YTCh. 5 - Prob. 5.6YTCh. 5 - Prob. 5.7YTCh. 5 - Prob. 5.8YTCh. 5 - Prob. 5.9YTCh. 5 - Prob. 5.10YTCh. 5 - Prob. 5.11YTCh. 5 - Prob. 5.12YTCh. 5 - Prob. 5.13YTCh. 5 - Prob. 5.14YTCh. 5 - Prob. 5.15YTCh. 5 - Prob. 5.16YTCh. 5 - Prob. 5.17YT
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