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Methyl group

In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane (CH4). It has the formula -CH3 and is often abbreviated -Me. Such hydrocarbon groups occur in many organic compounds.

Methyl groups can be incorporated into organic compounds by an SN2 reaction on iodomethane, or by the reaction of methyl lithium or MeMgCl with a carbon atom that is substituted with a leaving group.

Contents

Reactivity

The introduction of methyl groups as substituents into a compound usually increases its lipophilicity and reduces its solubility in water. It should ease its absorption into biological membranes and make its release into aqueous surroundings more difficult. Incorporating a methyl group into a molecule can have any of three effects, each increasing its reactivity (the rate of its metabolism):

  1. by oxidizing the methyl group,
  2. by demethylation (the transfer of the methyl group to another compound), or
  3. by reduction, reducing the analogue.

The reactivity of a methyl group depends on what it is attached to. When occurring in an alkane, it is quite unreactive and resists all but the strongest of acids, bases, oxidizing agents, and reducing agents. But, in toluene, C6H5CH3, the methyl group is considerably more reactive, due to the electron-donating propensity of the ring. Electrophilic reagents are then able to attack the methyl group. For example, oxidation with permanganate converts the methyl group to carboxyl (-COOH), to produce benzoic acid.

Methyl radical

The methyl radical is the substance CH3 on its own, with an unpaired electron. Though it readily dimerizes to ethane, it is stable enough (unlike atomic hydrogen) to be observed as a dilute gas. It can be produced by thermal decomposition of certain compounds, especially those with an -N=N- linkage, which lose the extremely stable dinitrogen molecule on heating.

Etymology

French chemists Jean-Baptiste Dumas and Eugene Peligot, after determining methanol's chemical structure, introduced "methylene" from the Greek methy = "wine" + hȳlē = wood (patch of trees) with the intention of highlighting its origins, "alcohol made from wood (substance)." The term "methyl" was derived in about 1840 by back-formation from methylene, and was then applied to describe "methyl alcohol."

See also

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Simple English

Methyl is an ion. It is made by removing one of the hydrogen atoms from an atom of methane. It is an organic ion. Its chemical formula is CH3. It bonds with other ions, such as hydroxide, to make chemical compounds. The bonding with hydroxide makes methanol. If it bonds with mercury, it makes dimethylmercury.

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