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関連する概念動画

Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

4.3K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
4.3K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.0K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
5.0K
Halogenation of Alkenes02:46

Halogenation of Alkenes

20.6K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
20.6K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.3K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.3K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.7K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
3.7K
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

18.2K
Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
18.2K

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脱ヒロゲン化後のC−CとC−Hコップリング

Huihui Kong, Sha Yang, Hongying Gao1,2

  • 1Physikalisches Institut, Westfälische Wilhelms-Universität Münster , Wilhelm-Klemm-Strasse 10, 48149 Münster, Germany.

Journal of the American Chemical Society
|February 11, 2017
PubMed
まとめ

研究者は銀の表面で選択的なC−H結合を達成し,新しい有機分子とポリマー鎖の合成を可能にしました. この画期的な発見は 表面化学を 伝統的なポリマー製造を超えて進めるものです

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科学分野:

  • 表面化学
  • 有機合成
  • ナノテクノロジー

背景:

  • 炭素-ハロゲン (C-X) 結合分裂による分子間炭素-炭素 (C-C) 結合は,ポリマーナノ構造の合成に不可欠である.
  • 末端の炭素で制御されていないC−H結合は,共性ポリマーの拡張を妨げ,その合成を制限する.
  • 脱ハロゲン化後の選択的C−H結合は,表面化学において未熟な領域である.

研究 の 目的:

  • 異なる金属表面での選択的C−H結合を調査する.
  • 制御された結合反応による新しい有機分子とポリマー鎖の合成の可能性を探求する.
  • 表面補助有機合成の分野を発展させるため

主な方法:

  • 高解像度表面イメージングのためのスキャニングトンネル顕微鏡 (STM).
  • 表面元素と化学状態の分析のためのX線光電子スペクトロスコーピー (XPS).
  • 反応機構とエネルギー学を理解するための密度関数理論 (DFT) の計算.

主要な成果:

  • 主要なC−C結合は,ゴールド (Au) の表面で観察された.
  • 選択的なC−H結合はシルバー (Ag) 表面で達成され,これは新しい発見である.
  • 選択的なC−H結合により,ポリマー鎖または新しい有機分子が合成される.

結論:

  • 選択的なC−H結合のための新しい方法がAg−111表面で実証された.
  • この選択的結合は,複雑な有機分子の表面補助合成のための新しい道を開きます.
  • この発見は,表面化学の範囲を in situ ポリマー製造を超えて広げています.