The compounds which on reaction with CH3 Mg I do not give methane are (1) CII3 CII2 NII2 (2) C2

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The compounds which on reaction with CH3 Mg I do not give...

The compounds which on reaction with $\mathrm{CH}_{3} \mathrm{Mg}$ I do not give methane are
(1) $\mathrm{CII}_{3} \mathrm{CII}_{2} \mathrm{NII}_{2}$
(2) $\mathrm{C}_{2} \mathrm{II}_{5} \mathrm{OII}$
(3) $\left(\mathrm{CII}_{3}\right)_{3} \mathrm{~N}$
(4) $\mathrm{NII}_{3}$

Key Concepts

Influence of Functional Groups on Reactivity

The reactivity pathway for a Grignard reagent is largely dependent on the functional groups present in the substrate. Compounds that do not contain hydrogen atoms bonded to electronegative atoms, and hence lack acidic protons, do not undergo the typical acid–base reaction that would yield methane. Instead, such substrates may allow the Grignard reagent to react by nucleophilic attack on electrophilic centers if they are available.

Reactivity of Polyhalogenated Compounds

Polyhalogenated compounds, which have many halogen atoms replacing hydrogens, generally lack any acidic protons. As a result, they do not engage in proton abstraction reactions with Grignard reagents to form methane. Their reactivity, if observed, follows other mechanisms such as nucleophilic substitution rather than the acid–base pathway.

Acid–Base Reaction Mechanism

When a Grignard reagent encounters a compound that has labile or acidic hydrogen atoms (for example, in –OH, –NH, or –COOH groups), it typically acts as a base by abstracting a proton. This acid–base reaction results in the formation of the corresponding hydrocarbon (such as methane in many cases) and a salt. The key determining feature is the presence of an accessible hydrogen with enough acidity to be removed.

Grignard Reagent Reactivity

Grignard reagents are highly nucleophilic and strongly basic organometallic compounds. They are capable of attacking electrophilic centers, such as those found in carbonyl groups, and can also deprotonate compounds that possess sufficiently acidic protons. Their reactivity is determined by the nature of the substrate, which can lead to nucleophilic addition or acid–base reactions.

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