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Chapter 4: Q28P (page 225)

The triphenylmethyl cation is so stable that some of its salts can be stored for months. Explain why this cation is so stable.

triphenylmethyl cation

Short Answer

Expert verified

The triphenylmethyl cation is extremely stable because it has three phenyl groups to stabilize the positive charge. The positive charge on carbon is in conjugation with three phenyl groups which make this carbocation more stable.

Step by step solution

01

Carbocation definition

A carbocation is a species that contains a carbon atom bearing a positive charge. The positively charged carbon atom is bonded to three other atoms, and it has no nonbonding electrons, so it has only six electrons in its valence shell.

02

Stability order of carbocation

The order of stability is

tertiary carbocation (most stable) >secondary carbocation>primary carbocation (least stable).

03

Step 3: Stability of triphenylmethyl cation

Here in triphenylmethyl cation, positive charge is on C-atom which is next to benzene (phenyl group) ring. This phenyl group helps in the delocalization of positive charge in the ring which makes them stable carbocation. Also there are three phenyl group which make further stable this triphenylmethyl carbocation.

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Most popular questions from this chapter

For each compound, predict the major product of free-radical bromination. Remember that bromination is highly selective, and only the most stable radical will be formed.

(a) cyclohexane

(b) methylcyclopentane

(c) decalin

(d) hexane

(e)

(f)

When exactly 1 mole of methane is mixed with exactly 1 mole of chlorine and light is shone on the mixture, a chlorination reaction occurs. The products are found to contain substantial amounts of di-, tri-, and tetrachloromethane, as well as unreacted methane.

(a) Explain how a mixture is formed from this stoichiometric mixture of reactants, and propose mechanisms for the formation of these compounds from chloromethane.

(b) How would you run this reaction to get a good conversion of methane toCH3Cl? Of methane to CCl4?

Acetylacetone (pentane -2, 4-dione)reacts with sodium hydroxide to give water and the sodium salt of a carbanion. Write a complete structural formula for the carbanion, and use resonance forms to show the stabilization of the carbanion.

Iodination of alkanes using iodine (I2)is usually an unfavorable reaction. (See problem 4-17, for example). Tetraiodomethane (Cl4) can be used as the iodine source for iodination in the presence of a free-radical initiator such as hydrogen peroxide. Propose a mechanism (involving mildly exothermic propagation steps) for the following proposed reaction. Calculate the value of ΔHfor each of the steps in your proposed mechanism.

The following bond-dissociation energies may be helpful:

When ethene is treated in a calorimeter with H2and a Ptcatalyst, the heat of reaction is found to be -137kJ/mol(-32.7kcal/mol), and the reaction goes to completion. When the reaction takes place at 14000K, the equilibrium is found to be evenly balanced, with Keq=1. Compute the value of ΔSfor this reaction.
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