Chemical Principles: The Quest for Insight
Chemical Principles: The Quest for Insight
7th Edition
ISBN: 9781464183959
Author: Peter Atkins, Loretta Jones, Leroy Laverman
Publisher: W. H. Freeman
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Chapter 2, Problem 2.46E

(a)

Interpretation Introduction

Interpretation:

Lewis structure of H2CCH2, H2CCCH2 and H2CCCCH2 has to be predicted.

Concept Introduction:

Lewis structures represent covalent bonds and describe valence electrons configuration of atoms. The covalent bonds are depicted by lines and unshared electron pairs by pairs of dots. The sequence to write Lewis structure of some molecule is given as follows:

  • The central atom is identified and various other atoms are arranged around it. This central atom so chosen is often the least electronegative.
  • Total valence electrons are estimated for each atom.
  • single bond is first placed between each atom pair.
  • The electrons left can be allocated as unshared electron pairs or as multiple bonds around the symbol of the element to satisfy the octet (or duplet) for each atom.
  • Add charge on the overall structure in case of polyatomic cation or anion.

(a)

Expert Solution
Check Mark

Explanation of Solution

H2CCH2 consists of C and H atoms. C possesses 4 valence electrons, H possesses 1 valence electron. Thus total valence electrons is the sum of the valence electrons for each atom along with a charge in H2CCH2. It is calculated as follows:

  Total valence electrons=4(2)+1(4)=12

Hence, 6 pairs are to be allocated to form the Lewis structure of H2CCH2. This can be done in the ethene molecule indicated as follows:

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  1

Similarly, total valence electrons is sum of the valence electrons for each atom along with a charge in H2CCCH2. It is calculated as follows:

  Total valence electrons=4(3)+1(4)=16

Hence, 8 pairs are to be allocated to form the Lewis structure of H2CCCH2 . This can be done whether as two double bonds in allene indicated as follows:

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  2

Likewise, total valence electrons in H2CCCCH2 is calculated as follows:

  Total valence electrons=4(4)+1(4)=20

Hence, 10 pairs are to be allocated to form the Lewis structure of H2CCCCH2. This can be done whether as two double bonds in allene indicated as follows:

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  3

(b)

Interpretation Introduction

Interpretation:

The hybridization at each carbon in H2CCH2, H2CCCH2 and H2CCCCH2 has to be assigned.

Concept Introduction:

The table that relates the steric number with hybridization is as follows:

Steric NumberType of Hybridisation2sp3sp24sp35sp3d6sp3d2

(b)

Expert Solution
Check Mark

Explanation of Solution

In the structure of H2CCCCH2 the hybridization at each carbon is illustrated below.

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  4

The terminal carbon atoms at positions 1 and 2 are trigonal planar with 3 as steric number hence the hybridization of these carbon atoms is sp2.

In the structure of H2CCCH2 the hybridization at each carbon is illustrated below.

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  5

Since the steric number around central carbon is 2 therefore, the hybridization of carbon atom located at positions 2 is sp. The terminal carbon atoms at positions 1 and 3 are trigonal planar with 3 as steric number hence the hybridization of carbon1 and 3  is sp2.

In the structure of H2CCCCH2 the hybridization at each carbon is illustrated below.

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  6

Central carbon atoms have effectively two bond pairs as each double bond is regarded as one single bond pair. Since the steric number around central carbon atoms is 2 therefore, the hybridization of carbon atoms located at positions 2 and 3 is sp.

The terminal carbon atoms at positions 1 and 4 are trigonal planar with 3 as steric number hence the hybridization of this carbon is sp2.

(c)

Interpretation Introduction

Interpretation:

The type of bonds that connect carbon atoms in H2CCH2, H2CCCH2 and H2CCCCH2 has to be identified.

Concept Introduction:

A single bond is always associated with sigma bonds. Molecules that have all atoms connected by sigma bond exclusively are stated to be in sp3 hybridization. It has a bond angle of 109.5°.

A double bond and carbocation are associated with sp2 hybridization. It has a bond angle of 120°.

A triple bond or central carbon structure similar to allene is always associated with sp hybridization. It has a bond angle of 180°.

(c)

Expert Solution
Check Mark

Explanation of Solution

In H2CCCCH2 the hybridization at each carbon is sp2 thus each carbon has a double bond.

In H2CCCH2 the hybridization at position 1 and 3 is sp2 thus carbon at these positions have a double bond. Hybridization of carbon at position 2 is sp and it has two double bonds.

In H2CCCCH2 the hybridization, terminal carbon is sp2 so thus carbon at these positions has a double bond. The hybridization at the central two carbon atoms is sp. Theses have two double bonds on each side.

(d)

Interpretation Introduction

Interpretation:

The bond angles in H2CCH2, H2CCCH2 and H2CCCCH2 have to be determined.

Concept Introduction:

Refer to part (c).

(d)

Expert Solution
Check Mark

Explanation of Solution

A single bond is always associated with sigma bonds. Molecules that have all atoms connected by sigma bond exclusively are stated to be in sp3 hybridization. It has a bond angle of 109.5 °.

A double bond and carbocation are associated with sp2 hybridization. It has a bond angle of 120 °.

A triple bond or central carbon structure similar to allene is always associated with sp hybridization. It has a bond angle of 180 °.

Thus the bond angles can be illustrated as follows:

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  7

(e)

Interpretation Introduction

Interpretation:

Whether all hydrogen atoms lie in the same plane or not in H2CCH2, H2CCCH2 and H2CCCCH2 has to be determined.

Concept Introduction:

Refer to part (c).

(e)

Expert Solution
Check Mark

Explanation of Solution

In allene, the central carbon that is double bonded to each carbon in different planes is sp hybridized while the two terminal carbon atoms are sp2 hybridized.

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  8

Thus the terminal hydrogen atom on carbon at position 1 is in a different plane than carbon at position 3 in case of H2CCCH2. However for structures with even number of carbon atoms as in H2CCCCH2 and ethane all four hydrogen atoms lie in the same plane.

(f)

Interpretation Introduction

Interpretation:

Orientation of hydrogen atoms at end of chain has to be determined.

Concept Introduction:

In allene, the central carbon that is double bonded to each carbon in different planes is sp hybridized while the two terminal carbon atoms are sp2 hybridized.

(f)

Expert Solution
Check Mark

Explanation of Solution

For structures with even number of carbon atoms, for example, consider the structure:

  H2C(C)xCH2       x=2,4,6...

Here, the relative position of the hydrogen atom is indicated as follows:

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  9

For structures with an odd number of carbon atoms, for example, consider the structure:

  H2C(C)xCH2       x=1,3,5...

Here, the relative position of the hydrogen atom is indicated as follows:

Chemical Principles: The Quest for Insight, Chapter 2, Problem 2.46E , additional homework tip  10

Thus structures with even a number of carbon atoms as in H2CCCCH2 and ethane all four hydrogen atoms lie in the same plane while in allene with odd number of carbon atom, hydrogen atoms are oriented in a different plane.

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Chemical Principles: The Quest for Insight

Ch. 2 - Prob. 2A.3ECh. 2 - Prob. 2A.4ECh. 2 - Prob. 2A.5ECh. 2 - Prob. 2A.6ECh. 2 - Prob. 2A.7ECh. 2 - Prob. 2A.8ECh. 2 - Prob. 2A.9ECh. 2 - Prob. 2A.10ECh. 2 - Prob. 2A.11ECh. 2 - Prob. 2A.12ECh. 2 - Prob. 2A.13ECh. 2 - Prob. 2A.14ECh. 2 - Prob. 2A.15ECh. 2 - Prob. 2A.16ECh. 2 - Prob. 2A.17ECh. 2 - Prob. 2A.18ECh. 2 - Prob. 2A.19ECh. 2 - Prob. 2A.20ECh. 2 - Prob. 2A.21ECh. 2 - Prob. 2A.22ECh. 2 - Prob. 2A.23ECh. 2 - Prob. 2A.24ECh. 2 - Prob. 2A.25ECh. 2 - Prob. 2A.26ECh. 2 - Prob. 2A.27ECh. 2 - Prob. 2A.28ECh. 2 - Prob. 2A.29ECh. 2 - Prob. 2A.30ECh. 2 - Prob. 2B.1ASTCh. 2 - Prob. 2B.1BSTCh. 2 - Prob. 2B.2ASTCh. 2 - Prob. 2B.2BSTCh. 2 - Prob. 2B.3ASTCh. 2 - Prob. 2B.3BSTCh. 2 - Prob. 2B.4ASTCh. 2 - Prob. 2B.4BSTCh. 2 - Prob. 2B.5ASTCh. 2 - Prob. 2B.5BSTCh. 2 - Prob. 2B.1ECh. 2 - Prob. 2B.2ECh. 2 - Prob. 2B.3ECh. 2 - Prob. 2B.4ECh. 2 - Prob. 2B.5ECh. 2 - Prob. 2B.6ECh. 2 - Prob. 2B.7ECh. 2 - Prob. 2B.8ECh. 2 - Prob. 2B.9ECh. 2 - Prob. 2B.10ECh. 2 - Prob. 2B.11ECh. 2 - Prob. 2B.12ECh. 2 - 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Prob. 2G.21ECh. 2 - Prob. 2G.22ECh. 2 - Prob. 2.1ECh. 2 - Prob. 2.2ECh. 2 - Prob. 2.3ECh. 2 - Prob. 2.4ECh. 2 - Prob. 2.5ECh. 2 - Prob. 2.6ECh. 2 - Prob. 2.7ECh. 2 - Prob. 2.8ECh. 2 - Prob. 2.9ECh. 2 - Prob. 2.10ECh. 2 - Prob. 2.11ECh. 2 - Prob. 2.12ECh. 2 - Prob. 2.13ECh. 2 - Prob. 2.14ECh. 2 - Prob. 2.17ECh. 2 - Prob. 2.19ECh. 2 - Prob. 2.22ECh. 2 - Prob. 2.23ECh. 2 - Prob. 2.24ECh. 2 - Prob. 2.25ECh. 2 - Prob. 2.26ECh. 2 - Prob. 2.27ECh. 2 - Prob. 2.28ECh. 2 - Prob. 2.29ECh. 2 - Prob. 2.30ECh. 2 - Prob. 2.31ECh. 2 - Prob. 2.32ECh. 2 - Prob. 2.33ECh. 2 - Prob. 2.34ECh. 2 - Prob. 2.35ECh. 2 - Prob. 2.36ECh. 2 - Prob. 2.37ECh. 2 - Prob. 2.39ECh. 2 - Prob. 2.40ECh. 2 - Prob. 2.41ECh. 2 - Prob. 2.42ECh. 2 - Prob. 2.43ECh. 2 - Prob. 2.44ECh. 2 - Prob. 2.45ECh. 2 - Prob. 2.46ECh. 2 - Prob. 2.47ECh. 2 - Prob. 2.48ECh. 2 - Prob. 2.49ECh. 2 - Prob. 2.50ECh. 2 - Prob. 2.51ECh. 2 - Prob. 2.52ECh. 2 - Prob. 2.53ECh. 2 - Prob. 2.54ECh. 2 - Prob. 2.55ECh. 2 - Prob. 2.56ECh. 2 - Prob. 2.57ECh. 2 - 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