EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393543971
Author: KARTY
Publisher: VST
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Chapter 2, Problem 2.11P
Interpretation Introduction

Interpretation:

The functional groups in table 1-6 that possess at least one H- bond acceptor but no H- bond donors, at least one H- bond donor and H- bond acceptor, and no H- bond donors and no H- bond acceptors are to be given.

Concept introduction:

An H- bond donor is an H atom that is covalently bonded to a strongly electronegative atom such as N, O or F and the H- bond acceptor is the neighboring electronegative ion or molecule which must possess a lone pair of electrons.

Expert Solution & Answer
Check Mark

Answer to Problem 2.11P

(A) The names of the functional groups from the given table that possess at least one H- bond acceptor but no H-bond donors are: Nitrile, Ether, Ketone, Acetal, Aldehyde, Alkyl halide (Only if X = F), Epoxide, Ester, Amine and Amide.

(B) The names of the functional groups from the given table which possess at least one H- bond donor and one H- bond acceptor are: Hemiacetal, Carboxylic acid, Alcohol, and Phenol.

(C) The functional groups from the given table which possess no H-bond donors and no H- bond acceptors are Alkene, Thiol, Alkyne, Arene or aromatic compound, Alkyl halide (Only if X = Cl, Br, I).

Explanation of Solution

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 1

(A) The functional groups from the given table which possess at least one H- bond acceptor but no H- bond donors are:

  1. The given functional group is Nitrile:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 2

In this functional group, due to the high electronegativity of the N atom with a lone pair of electrons, there is one H-bond acceptor.

2) The given functional group is Ether:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 3

In this functional group, due to the high electronegativity of the O atom with a lone pair of electrons, there is one H-bond acceptor.

3) The given functional group is Ketone:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 4

In this functional group, due to the high electronegativity of the O atom with a lone pair of electrons, there is one H-bond acceptor.

4) The given functional group is Acetal:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 5

In this functional group, due to the high electronegativity of the O atom with a lone pair of electrons, there are two H-bond acceptors.

  1. The given functional group is Aldehyde:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 6

In this functional group, due to the high electronegativity of the O atom with a lone pair of electrons, there is one H-bond acceptor.

  1. The given functional group is Alkyl halide (Only if X = F):

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 7

In this functional group, due to the high electronegativity of the F atom with a lone pair of electrons, there is one H-bond acceptor.

  1. The given functional group is Epoxide:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 8

In this functional group, due to the high electronegativity of the O atom with a lone pair of electrons, there is one H-bond acceptor.

  1. The given functional group is Ester:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 9

In this functional group, due to the high electronegativity of the O atoms with a lone pair of electrons, there are two H-bond acceptors.

  1. The given functional group is Amine:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 10

In this functional group, due to the high electronegativity of the N atom with a lone pair of electrons, there is one H-bond acceptor.

  1. The given functional group is Amide:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 11

In this functional group, due to the high electronegativity of the N atom with a lone pair of electrons, there is one H-bond acceptor.

(B) The functional groups possessing at least one H-bond donor and one H-bond acceptor are:

1) The given functional group is Hemiacetal:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 12

In this functional group, there is one H-bond donor and two H-bond acceptors. The high electronegativity of the O atom ensures that the O-H bond is highly polar and gives the H atom a large partial positive charge. This sets up a strong attraction between the H atom and the oppositely charged acceptor.

2) The given functional group is Carboxylic acid:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 13

In this functional group, there is one H-bond donor and two H-bond acceptors. The high electronegativity of the O atom ensures that the O-H bond is highly polar and gives the H atom a large partial positive charge. This sets up a strong attraction between the H atom and the oppositely charged acceptor.

  1. The given functional group is Alcohol:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 14

In this functional group, there is one H-bond donor and one H-bond acceptor. The high electronegativity of the O atom ensures that the O-H bond is highly polar and gives the H atom a large partial positive charge. This sets up a strong attraction between the H atom and the oppositely charged acceptor.

4) The given functional group is Phenol:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 15

In this functional group, there is one H-bond donor and one H-bond acceptor. The high electronegativity of the O atom ensures that the O-H bond is highly polar and gives the H atom a large partial positive charge. This sets up a strong attraction between the H atom and the oppositely charged acceptor.

(C) The functional groups from the given table which possess no H-bond donor and no H-bond acceptor are:

1) The given functional group is Alkene:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 16

In this functional group, there is no H atom which is covalently bonded to a strongly electronegative atom such as N, O, or F. Therefore, there is no H-bond donor and H-bond acceptor.

2) The given functional group is Thiol:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 17

In this functional group, there is no H atom which is covalently bonded to a strongly electronegative atom such as N, O, or F. Therefore, there is no H-bond donor and H-bond acceptor.

3) The given functional group is Alkyne:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 18

In this functional group, there is no H atom which is covalently bonded to a strongly electronegative atom such as N, O, or F. Therefore, there is no H-bond donor and H-bond acceptor.

  1. The given functional group is Arene or aromatic compound:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 19

In this functional group, there is no H atom which is covalently bonded to a strongly electronegative atom such as N, O, or F. Therefore, there is no H-bond donor and H-bond acceptor.

  1. The given functional group is Alkyl halide (Only if X = Cl, Br, I): EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 2, Problem 2.11P , additional homework tip 20

In this functional group, there is no H atom which is covalently bonded to a strongly electronegative atom such as N, O, or F. Therefore, there is no H-bond donor and H-bond acceptor.

Conclusion

The H-bond donor and H-bond acceptor of the given compounds are predicted on the basis of the number of electronegative atoms that are covalently bonded with hydrogen atoms and with a large concentration of negative charge and lone pair of electrons.

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Chapter 2 Solutions

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M

Ch. 2 - Prob. 2.1PCh. 2 - Prob. 2.2PCh. 2 - Prob. 2.3PCh. 2 - Prob. 2.4PCh. 2 - Prob. 2.5PCh. 2 - Prob. 2.6PCh. 2 - Prob. 2.7PCh. 2 - Prob. 2.8PCh. 2 - Prob. 2.9PCh. 2 - Prob. 2.10P
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