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By taking into account electronegativity differences, draw the products formed by heterolysis of the carbon-heteroatom bond in each molecule. Classify the organic reactive intermediate as a carbocation or a carbanion.

Short Answer

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Answer

a. Intermediate formed is the carbocation.

b. The reactive intermediate formed is the carbocation.

c. The reactive intermediate formed is carbanion.

Step by step solution

01

Step-by-Step SolutionStep 1: Electronegativity

The ability/potential of an atom to pull electron density from a bond shared with another atom towards itself is referred to as its electronegativity.

The electronegative atom bears a partial negative charge and the less electronegative one bears a partial positive charge.

02

Carbocation and Carbanion

A carbon atom bearing a positive charge on itself is termed as carbocation and the one bearing a negative charge is termed as carbanion.

A carbon atom bonded to atoms having electronegativity higher than carbon leads to the generation of a carbocation and the ones bonded to atoms having less electronegativity than carbon result in the formation of a carbanion.

03

Heterolysis

Heterolysis means the breakage of a bond in which one atom acquires both the shared pair of electrons.

The atom attaining excess electrons will bear a negative charge and the other will acquire a positive charge.

04

Heterolysis in the given compounds

a.

Heterolysis of a carbon-oxygen bond

The heterolysis of the carbon-oxygen (C-O) bond in the given compound generates a carbocation as the electrons shared between carbon and oxygen get transferred to the more electronegative oxygen atom.

b.

Heterolysis of carbon-bromine bond

The bromine atom is more electronegative than carbon and hence the electrons are transferred onto the bromine atom.

Thus, the heterolysis of the carbon-bromine bond generates a carbocation.

c.

Heterolysis of carbon-lithium bond

The carbon atom is more electronegative compared to lithium and hence it will pull the electrons towards itself thereby generating a carbanion.

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Most popular questions from this chapter

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.

As we learned in Chapter 4, monosubstituted cyclohexanes exist as an equilibrium mixture of two conformations having either an axial or equatorial substituent. When R=CH2CH3, Keqfor this process is 23. When R=C(CH3)3,Keqfor this process is 4000.

a. When , which conformation is present in higher concentration?

b. Which R shows the higher percentage of equatorial conformation at equilibrium?

c. Which R shows the higher percentage of axial conformation at equilibrium?

d. For which R is more negative?

e. How is the size of R related to the amount of axial and equatorial conformations at equilibrium?

Follow the curved arrows and draw the products of the following reaction.

Compound A can be converted to either B or C. The energy diagrams for both processes are drawn on the graph below.

  1. Label each reaction as endothermic or exothermic.
  2. Which reaction is faster?
  3. Which reaction generates the product lower in energy?
  4. Which points on the graphs correspond to transition states?
  5. Label the energy of activation for each reaction.
  6. Label the ∆H° for each reaction.

Label each statement as true or false. Correct any false statement to make it true.

a. Increasing temperature increases reaction rate.

b. If a reaction is fast, it has a large rate constant.

c. A fast reaction has a large negative ∆G°value.

d. When Eais large, the rate constant k is also large.

e. Fast reactions have equilibrium constants > 1.

f. Increasing the concentration of a reactant always increases the rate of a reaction.

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