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Rank the indicated bonds in order of increasing bond dissociation energy.

Short Answer

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Answer

The bond dissociation energy increases in the order:I-CCl3<Br-CCl3<Cl-CCl3

Step by step solution

01

Step-by-Step SolutionStep 1: Bond dissociation Energy

The energy applied to dissociate a bond is called bond dissociation energy.

The bond dissociation energy is directly proportional to the strength of the bond.

Inorganic compounds, alkanes have the least bond dissociation energy. Alkenes have higher bond dissociation energy. In comparison, alkynes have the maximum bond dissociation energy.

02

Factors affecting Bond Dissociation Energy

There are various factors on which the amount of energy required to break the bonds depends. These factors are described hereunder:

  • Bond length: Shorter the bond length, the greater is the strength of the chemical bond. Hence, Bond Dissociation energy is higher and vice-versa.
  • The number of electrons shared: the number of electrons shared implies the number of chemical bonds existing between two atoms or groups.

Hence, the more the number of electrons is shared, the number of bonds and bond strength increases between two atoms. Hence, bond dissociation energy increases and vice-versa.

  • Atomic size: the larger the atomic size, the more is the bond length. Hence, the bond strength is less, and so bond dissociation energy is also less.
03

Comparison of bond dissociation energy in the given compounds

In the given three structures, the three halogens, i.e., chlorine, iodine, and bromine, are bonded with a single bond to the same chemical moiety.

The basis of comparing the Bond Dissociation energy for the three given structures is the atomic size of the halogen atoms attached.

Among Cl-CCl3,Br-CCl3andI-CCl3, chlorine has the smallest size, bromine has the intermediate size, and iodine has the largest size. Hence, the Cl-C bond length is the smallest, Br-C bond length is intermediate, and I-C bond length is the largest. Comparison of bond lengths

Thus, the bond strength increases in the order: I-C < Br-C <Cl-C

Hence, the bond dissociation energy also has the same order as the bond strength as I-CCl3<Br-CCl3<Cl-CCl3.

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Most popular questions from this chapter

As we will learn in Section 15.12, many antioxidants—compounds that prevent unwanted radical oxidation reactions from occurring—are phenols, compounds that contain an OH group bonded directly to a benzene ring.

  1. Explain why homolysis of the O-H bond in phenol requires considerably less energy than homolysis of the O-H bond in ethanol (362 kJ/mol vs 438 kJ/mol).
  2. Why is the C-O bond in phenol shorter than C-O bond in ethanol?

The Diels–Alder reaction, a powerful reaction discussed in Chapter 16, occurs when a 1,3- diene such as A reacts with an alkene such as B to form the six-membered ring in C.

a. Draw curved arrows to show how A and B react to form C.

b. What bonds are broken and formed in this reaction?

c. Would you expect this reaction to be endothermic or exothermic?

d. Does entropy favor the reactants or products?

e. Is the Diels–Alder reaction a substitution, elimination, or addition?

Which bond in each pair has the higher bond dissociation energy?

a.

b.

What carbon radical is formed by homolysis of theC-Ha bond in propylbenzene? Draw all reasonable resonance structures for this radical.

What carbon radical is formed by homolysis of therole="math" localid="1648540916945" C-Hbbond in propylbenzene? Draw all reasonable resonance structures for this radical.

The bond dissociation energy of one of the C-H bonds is considerably less than the bond dissociation energy of the other. Which C-H bond is weaker? Offer an explanation.

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?

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