Chemistry: The Molecular Science
Chemistry: The Molecular Science
5th Edition
ISBN: 9781285199047
Author: John W. Moore, Conrad L. Stanitski
Publisher: Cengage Learning
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Alkynes
Alkynes are organic compounds that contain at least one triple bond between carbon-carbon atoms. They are a series of unsaturated compounds with a general molecular formula, CnH2n-2.
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Chapter 10, Problem 122QRT

(a)

Interpretation Introduction

Interpretation:

The chemical equation of addition reaction of 3-Hexene with HCl has to be stated with help of Lewis structures.

Concept Introduction:

The addition of one or more than one halogen atom in alkene is known as halogenation reaction.  The pathway of the halogenation reaction depends on the structure of the substrate.  In this the halogen is added to C=C bond of the alkene to form haloalkane.

(a)

Expert Solution
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Explanation of Solution

The halogenation reaction of 3-Hexene gives an alkyl halide, 3-chlorohexene.  The alkene has a π bond in it.  The π bond of 3-Hexene gets brake to form 3-chlorohexene. The chloro-group is added to the third carbon atom and the hydrogen atom is added to the fourth carbon atom.  The corresponding chemical reaction is shown below.

Chemistry: The Molecular Science, Chapter 10, Problem 122QRT , additional homework tip 1

Figure 1

(b)

Interpretation Introduction

Interpretation:

The standard enthalpy change for the overall addition reaction of 3-Hexene with HCl has to be calculated.

Concept Introduction:

The amount of energy which is produced or absorbed during the reaction is the enthalpy change of a chemical reaction.  When bonds gets break, some amount of energy is absorbed by the system.  When bonds are formed, some amount of energy is produced by the system.

(b)

Expert Solution
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Explanation of Solution

The overall addition reaction of 3-Hexene with HCl  is shown below.

Chemistry: The Molecular Science, Chapter 10, Problem 122QRT , additional homework tip 2

Figure 1

The reactant 3-Hexene has 12 C−H bonds, 4 C−C bonds and a C=C bond.

The reactant HCl has a H−Cl bond.

The product octane has 13 C−H bonds, a C−Cl bond and 5 C−C bonds.

The bond enthalpy for C−H is 416 kJ/mol.

The bond enthalpy for C=C is 598 kJ/mol.

The bond enthalpy for C−C is 356 kJ/mol.

The bond enthalpy for C−Cl is 327 kJ/mol.

The bond enthalpy for H−Cl is 431 kJ/mol.

The standard enthalpy change for the overall reaction is calculated by the formula as shown below.

  ΔH°=(∑[(number of bonds)×D(bonds broken)]−∑[(number of bonds)×D(bonds formed)])

Where,

  • ΔH° is the standard enthalpy change for the overall reaction.
  • D is the bond enthalpy.

The above equation can rewritten for addition reaction of 3-Hexene with HCl as shown below.

  ΔH°=[(12×D(C−H)+4×D(C−C)+D(C=C))+D(H−Cl)−(13×D(C−H)+D(C−Cl)+5×D(C−C))]

Substitute the value of bond enthalpy for C−H, bond enthalpy for C−Cl, bond enthalpy for C=C, bond enthalpy for C−C, and bond enthalpy for H−Cl in the above equation.

  ΔH°=[(12×(416 kJ/mol)+4×(356 kJ/mol)+(598 kJ/mol))+(431 kJ/mol)−(13×(416 kJ/mol)+(327 kJ/mol)+5×(356 kJ/mol))]=[4992+1424+598+431−5408−327−1780] kJ/mol=[7445−7515] kJ/mol=−70 kJ/mol_

The standard enthalpy change for the overall addition reaction of 3-Hexene with HCl is −70 kJ/mol_.

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