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Homolysis of the indicated C-H bond in propene forms a resonance-stabilized radical.

  1. Draw the two possible resonance structures for this radical.
  2. Use half-headed curved arrows to illustrate how one resonance structure can be converted to the other.
  3. Draw a structure for the resonance hybrid.

Short Answer

Expert verified

Answer

a.Resonance structures of Propene

b.

Half-headed arrows showing the interconversion of resonance structures of Propene

c.Resonance Hybrid structure

Step by step solution

01

Step-by-Step SolutionStep 1: Bond dissociation Energy

The Bond Dissociation energy determines the bond strength. The stronger the bond, the more is the bond dissociation energy and vice-versa.

The bond dissociation energy is positive.

02

Enthalpy change

The difference in the energy of the products and the reactants is called the enthalpy change of the reaction. The enthalpy change determines the relative bond strength of the reactants and the products.

For endothermic reactions, the enthalpy change is positive. In comparison, for the exothermic reactions, the

enthalpy change is negative.

When the bonds break, the ∆H°is positive; when the new bonds are formed, the ∆H° is negative.

03

Enthalpy change of the given compounds

The resonance stabilized radical formed upon the homolytic bond fission of the indicated C-H bond is shown hereunder.

a. The two resonance structures are:


Resonance structures of Propene

b. The half-headed curved arrows to inter-convert the two resonance structures are shown hereunder.

Half-headed arrows showing the interconversion of resonance structures of Propene

c. For the resonance hybrid, the electron density of the single radical electron is shown above the two bonds under the effect of resonance.

Resonance Hybrid structure

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Most popular questions from this chapter

(a) Add curved arrows for each step to show how A is converted to the epoxy ketone C. (b) Classify the conversion of A to C as a substitution, elimination, or addition. (c) Draw one additional resonance structure for B.

Consider the following reaction: CH4+Cl·→·CH3+HCl.

a. Use curved arrows to show the movement of electrons.

b. Calculate ∆H°using the bond dissociation energies in Table 6.2.

c. Draw an energy diagram assuming that Ea=16kJ/mol.

d. What is Eafor the reverse reaction (·CH3+HCl→CH4+Cl·)?

Question: Draw an energy diagram for a reaction in which the products are higher in energy than the starting materials and Eais large. Clearly label all of the following on the diagram: the axes, the starting materials, the products, the transition state, ∆H°,and Ea.

The following is a concerted, bimolecular reaction:CH3+NaCN→CH3CN+NaBr.

a. What is the rate equation for this reaction?

b. What happens to the rate of the reaction if[CH3Br] is doubled?

c. What happens to the rate of the reaction if [NaCN] is halved?

d. What happens to the rate of the reaction if [CH3Br] and [NaCN] are both increased by a factor of five?

Calculate Δ±á° for each oxidation reaction. Each equation is balanced as written; remember to take into account the coefficients in determining the number of bonds broken or formed.

[ Δ±á∘for O2=497kJ/mol ; Δ±á∘for one C=O in CO2=535kJ/mol]

a.role="math" localid="1648191068323" CH4+2O2→CO2+2H2O

b.2CH4+7O2→4CO2+6H2O


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