Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 5, Problem 5.45P
Interpretation Introduction

(a)

Interpretation: The given groups are to be ranked in the order of decreasing priority.

Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

The priorities of the atoms that are directly attached to the stereogenic center are assigned in the order of decreasing atomic number. An atom of highest atomic number gets highest priority.

Expert Solution
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Answer to Problem 5.45P

The decreasing order of priority is OH>NH2>CH3.

Explanation of Solution

The priority can be assigned by numbering the groups which are bonded to the chiral carbon atom based on the molecular weight and electronegativity.

In the given groups, the atomic number of nitrogen is 7, carbon is 6 and oxygen is 8. An atom of highest atomic number gets highest priority. Therefore, the decreasing order of priority is OH>NH2>CH3.

Conclusion

The decreasing order of priority for the given groups is OH>NH2>CH3.

Interpretation Introduction

(b)

Interpretation: The given groups are to be ranked in the order of decreasing priority.

Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

The priorities of the atoms that are directly attached to the stereogenic center are assigned in the order of decreasing atomic number. An atom of highest atomic number gets highest priority.

Expert Solution
Check Mark

Answer to Problem 5.45P

The decreasing order of priority for the given groups is (CH2)3CH3>CH2CH2CH3>CH2CH3>CH3.

Explanation of Solution

The priority can be assigned by numbering the groups which are bonded to the chiral carbon atom based on the molecular weight and electronegativity.

The given groups are CH3CH2CH3CH2CH2CH3(CH2)3CH3. When the stereogenic center contains same number of atoms attached to it then, the priority is assigned on the basis of the atomic number of atoms which are bonded to these atoms. An atom of highest atomic number gets highest priority.

Therefore, the decreasing order of priority for the given groups is (CH2)3CH3>CH2CH2CH3>CH2CH3>CH3.

Conclusion

The decreasing order of priority for the given groups is (CH2)3CH3>CH2CH2CH3>CH2CH3>CH3.

Interpretation Introduction

(c)

Interpretation: The given groups are to be ranked in the order of decreasing priority.

Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

The priorities of the atoms that are directly attached to the stereogenic center are assigned in the order of decreasing atomic number. An atom of highest atomic number gets highest priority.

Expert Solution
Check Mark

Answer to Problem 5.45P

The decreasing order of priority is NH2>CH2NHCH3>CH2NH2>CH3.

Explanation of Solution

The priority can be assigned by numbering the groups which are bonded to the chiral carbon atom based on the molecular weight and electronegativity.

In the given groups, the atomic number of nitrogen is 7 and carbon is 6. An atom of highest atomic number gets highest priority. Therefore, NH2 gets highest priority. When the stereogenic center contains same number of atoms attached to it then, the priority is assigned on the basis of the atomic number of atoms which are bonded to these atoms. An atom of highest atomic number gets highest priority.

Hence, the decreasing order of priority is NH2>CH2NHCH3>CH2NH2>CH3.

Conclusion

The decreasing order of priority for the given groups is NH2>CH2NHCH3>CH2NH2>CH3.

Interpretation Introduction

(d)

Interpretation: The given groups are to be ranked in the order of decreasing priority.

Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

The priorities of the atoms that are directly attached to the stereogenic center are assigned in the order of decreasing atomic number. An atom of highest atomic number gets highest priority.

Expert Solution
Check Mark

Answer to Problem 5.45P

The decreasing order of priority is COOH > CHO > CH2OH > H.

Explanation of Solution

The priority can be assigned by numbering the groups which are bonded to the chiral carbon atom based on the molecular weight and electronegativity.

In the given groups, the atomic number of carbon is 6, oxygen is 8 and hydrogen is 1. An atom of highest atomic number gets highest priority. Therefore, H gets lowest priority. For an atom which is a part of multiple bonds, the priority is assigned by treating the number of multiple bonded atoms equivalent to the number of singly bonded atoms. Among COOH, CH2OH, CHO, the priority is assigned as,

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.45P , additional homework tip  1

Figure 1

Hence, the decreasing order of priority is COOH > CHO > CH2OH > H.

Conclusion

The decreasing order of priority for the given groups is COOH > CHO > CH2OH > H.

Interpretation Introduction

(e)

Interpretation: The given groups are to be ranked in the order of decreasing priority.

Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

The priorities of the atoms that are directly attached to the stereogenic center are assigned in the order of decreasing atomic number. An atom of highest atomic number gets highest priority.

Expert Solution
Check Mark

Answer to Problem 5.45P

The decreasing order of priority is Cl>SH>OH>CH3.

Explanation of Solution

The priority can be assigned by numbering the groups which are bonded to the chiral carbon atom based on the molecular weight and electronegativity.

In the given groups, the atomic number of chlorine is 17, sulphur is 16, carbon is 6 and oxygen is 8. An atom of highest atomic number gets highest priority. Therefore, the decreasing order of priority is Cl>SH>OH>CH3.

Conclusion

The decreasing order of priority for the given groups is Cl>SH>OH>CH3.

Interpretation Introduction

(f)

Interpretation: The given groups are to be ranked in the order of decreasing priority.

Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

The priorities of the atoms that are directly attached to the stereogenic center are assigned in the order of decreasing atomic number. An atom of highest atomic number gets highest priority.

Expert Solution
Check Mark

Answer to Problem 5.45P

The decreasing order of priority for the given groups is CCH > CH=CH2 > CH(CH3)2 > CH2CH3.

Explanation of Solution

The priority can be assigned by numbering the groups which are bonded to the chiral carbon atom based on the molecular weight and electronegativity.

An atom of highest atomic number gets highest priority. Therefore, in the given groups, CH2CH3 gets lowest priority.

For an atom which is a part of multiple bonds, the priority is assigned by treating the number of multiple bonded atoms equivalent to the number of singly bonded atoms. Among, CCH, CH(CH3)2CH=CH2 the priority is assigned as,

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.45P , additional homework tip  2

Figure 2

Hence, the decreasing order of priority for the given groups is CCH > CH=CH2 > CH(CH3)2 > CH2CH3.

Conclusion

The decreasing order of priority for the given groups is CCH > CH=CH2 > CH(CH3)2 > CH2CH3.

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Chapter 5 Solutions

Organic Chemistry-Package(Custom)

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