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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

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

Question: When ethene is mixed with hydrogen in the presence of a platinum catalyst, hydrogen adds across the double bond to form ethane. At room temperature, the reaction goes to completion. Predict the signs ∆H0and∆S0for this reaction. Explain these signs in terms of bonding and freedom of motion.

(a) When n-heptaneburns in a gasoline engine, the combustion process takes place too quickly. The explosive detonation makes a noise called knocking. When 2,2,4 trimethylpentane (isooctane) is burned, combustion takes place in a slower, more controlled manner. Combustion is a free-radical chain reaction, and its rate depends on the reactivity of the free-radical intermediates. Explain why isooctane has less tendency to knock than doesn-heptane

(b) Alkoxy radicals (R-O)are generally more stable than alkyl (R) radicals. Write an equation showing an alkyl free radical (from burning gasoline) abstracting a hydrogen atom from tert-butyl alcohol,(CH3)3COH. Explain whytert-butyl alcohol works as an antiknock additive for gasoline.

(c) Use the information in Table 4-2 (page 203) to explain why toluene (PhCH3) has a very high-octane rating of 111. Write an equation to show how toluene reacts with an alkyl free radical to give a relatively stable radical.

Treatment oftert - butyl alcohol with concentrated HBrgives tert butyl bromide.

When the concentration of H+is doubled, the reaction rate doubles. When the concentration of tert- butyl alcohol is tripled, the reaction rate triples. When the bromide ion concentration is quadrupled, however, the reaction rate is unchanged. Write the rate equation for this reaction.

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?
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