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Grignard reagent A Grignard reagent is prepared by the reaction of magnesium metal with an organohalogen compound in an ether solvent. An ether solvent is necessary for the formation of the Grignard reagent. It is thought that the unshared electrons of the oxygen coordinate with the Mg to stabilize the organometallic compound. Also, the alkyl portion of the ether provides a hydrocarbon-like solvent for the organic part of the Grignard reagent. Both these factors result in Grignard reagents being soluble in ethers. Diethyl ether is the usual solvent because it is inexpensive. Other ethers, such as tetrahydrofuran, can also be used. Grignard reagents are extremely strong bases that react with acids, alcohols, amines, water, and even such weak acids as alkynes with a terminal triple bond (RC≡CH, pKa 26). In these reactions, the R of RMgX removes a proton from the acidic compound and becomes an alkane (RH). Because acid-base reactions are very rapid compared to other organic reactions, a compound with a removable H+ quickly destroys a Grignard reagent. Therefore in carrying out a Grignard reaction, we must use scrupulously dry glassware, solvents, and reagents. In addition, the reagents must not contain a group with a reactive hydrogen unless an alkane is the desired product. In the reaction with a carbonyl compound, the organic portion of a Grignard reagent acts as a strong nucleophile and attacks the partially positive carbonyl carbon to yield a magnesium alkoxide. Subsequent treatment of the alkoxide with aqueous acid yields the alcohol itself.

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グリニャール試薬 グリニャール試薬は、エーテル系溶媒の有機ハロゲン化合物と金属マグネシウムの反応によって調製されています。 エーテル系溶媒は、グリニャール試薬を形成するために必要である。それは酸素の非共有電子が有機金属化合物を安定化させるためにMgを調整すると考えられている。また、エーテルのアルキル部分は、グリニャール試薬の有機部分の炭化水素のような溶剤を提供しています。エーテルに可溶であるグリニャール試薬のこれらの要因の結果の両方。 それが安価であるためジエチルエーテルは、通常の溶媒である。テトラヒドロフランなどのエーテル類は、使用することもできます。 グリニャール試薬は酸、アルコール、アミン、水、さらには端末の三重結合(RC≡CH、pKaが26)アルキンなどの弱い酸と反応し非常に強い塩基である。これらの反応では、RMgXのRは、酸性化合物からプロトンを除去し、アルカン(RH)となります。 酸塩基反応は他の有機反応は、取り外し可能なHの化合物+迅速にグリニャール試薬を破壊しに比べて非常に急速であるためです。したがって、グリニャール反応を行うことで、我々は綿密に乾燥したガラス製品、溶剤、試薬を使用する必要があります。アルカンは、所望の生成物でない限り、さらに、試薬は反応性水素を持つグループを含めることはできません。 カルボニル化合物との反応では、グリニャール試薬の有機部分は、強力な求核剤として作用し、マグネシウムアルコキシドを生成するために、部分的に正のカルボニル炭素を攻撃する。 酸水溶液でアルコキシドのその後の治療が得られます。 こんな感じです。

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