Some bond dissociation energies in kJ/mol are listed. 1°, 2°, 3° means primary, secondary,tertiary.1° C-H 423 2° C-H 413 3° C-H 4041° C-CN 509 2° C-CN 506 3° C-CN 493For the hypothetical reaction below, do two things:1) Estimate the enthalpy change ΔH° for the reaction. Show your work in the space below.2) Draw a circle around the molecule with the lower enthalpy. **Alkyl Chain Rearrangement Reaction**This image illustrates a chemical reaction involving a rearrangement of an alkyl chain. **Reactant Structure:**- The starting molecule is a straight-chain alkane with five carbon atoms and a terminal cyanide group (CN).- The chain is branched at the second carbon, indicating isopropyl substitution.**Product Structure:**- The product of the reaction shows the cyanide group migrating from the terminal position to a secondary carbon, resulting in an internal shift.- This change forms a more substituted and potentially more stable carbon structure with improved branching.**Explanation:**- This reaction exemplifies the behavior of cyanide substitution in alkanes, highlighting the importance of molecular stability in organic chemistry.- Such rearrangements are common in synthetic organic processes, often guided by factors like steric hindrance and electronic stability.This reaction is a fundamental illustration used in advanced organic chemistry topics to teach about rearrangement mechanisms.

Answered: Some bond dissociation energies in…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Some bond dissociation energies in kJ/mol are listed. 1°, 2°, 3° means primary, secondary,
tertiary.
1° C-H 423 2° C-H 413 3° C-H 404
1° C-CN 509 2° C-CN 506 3° C-CN 493
For the hypothetical reaction below, do two things:
1) Estimate the enthalpy change ΔH° for the reaction. Show your work in the space below.
2) Draw a circle around the molecule with the lower enthalpy.

**Alkyl Chain Rearrangement Reaction**

This image illustrates a chemical reaction involving a rearrangement of an alkyl chain.

**Reactant Structure:**
- The starting molecule is a straight-chain alkane with five carbon atoms and a terminal cyanide group (CN).
- The chain is branched at the second carbon, indicating isopropyl substitution.

**Product Structure:**
- The product of the reaction shows the cyanide group migrating from the terminal position to a secondary carbon, resulting in an internal shift.
- This change forms a more substituted and potentially more stable carbon structure with improved branching.

**Explanation:**
- This reaction exemplifies the behavior of cyanide substitution in alkanes, highlighting the importance of molecular stability in organic chemistry.
- Such rearrangements are common in synthetic organic processes, often guided by factors like steric hindrance and electronic stability.

This reaction is a fundamental illustration used in advanced organic chemistry topics to teach about rearrangement mechanisms.

Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

Expert Solution

Step 1: Introduction

In the given reaction a primary cyano group is converted to a tertiary cyano group.

Now, in the overall reaction a primary cynano and tertiary C-H bond breaks in the reactant, whereas a tertiary cynano and primary C-H bond forms in the product.

Whenever bonds are formed energy is released (conventionally has -ve sign) and bonds are breakes energy is consumed (conventionally has +ve sign).

Here we will calculate the overall energy of the species taking positive values. The species with greater positive energy value will be considered as more stable (as conventionally it has higher negative energy i.e. lesser energy).

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