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Chapter 4: Q 52P (page 236)

When dichloromethane is treated with strong NaOH , an intermediate is generated that reacts like a carbene. Draw the structure of this reactive intermediate, and propose a mechanism for its formation.

Short Answer

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mechanism of the reaction

structure of the reactive intermediate (carbene)

Step by step solution

01

Carbenes

Carbenes may be defined as a neutral divalent chemical species containing a carbon atom consisting six electrons in their valence shell. Out of six electrons, two electrons are unshared. The simplest carbene is methylene CH2 .

02

Mechanism for the formation of reactive intermediate

Dichloromethane when treated with strong sodium hydroxide solution yields an intermediate that reacts more like a carbene.

Deprotonation of dichloromethane with sodium hydroxide takes place in the first step. The second step is the chlorine anion leaving the molecule to give the intermediate.

mechanism of the reaction

structure of the reactive intermediate (carbene)

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Most popular questions from this chapter

In the presence of a small amount of bromine, cyclohexene undergoes the following light-promoted reaction:

(a) Propose a mechanism for this reaction.

(b) Draw the structure of the rate-limiting transition state.

(c) Use Hammond鈥檚 postulate to predict which intermediate most closely resembles this transition state.

(d) Explain why cyclohexene reacts with bromine much faster than cyclohexane, which must be heated to react.

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?

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 螖贬for each of the steps in your proposed mechanism.

The following bond-dissociation energies may be helpful:

Use bond-dissociation enthalpies (Table 4-2, p.203) to calculate values of螖贬for the following reactions.

(a)

(b)

(c)

(d)

(e)

Question: Draw Lewis structures for the following free radicals.

(a)The ethyl radical, CH3-CH2

(b)The tert butyl radical, (CH3 )3C

(c)The isopropyl radical,(2-propyl radical)

(d)The iodine atom
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