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質量輸送依存C−C結合形成

  • 0School of Chemical Engineering and Technology, Xi'an Jiaotong University, Xi'an 710049, People's Republic of China.

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Hydroboration-Oxidation of Alkenes 03:08

7.8K

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Borane as a reagent is very reactive, as the...

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate 02:21

10.7K

Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.

The mechanism begins with the syn addition of a permanganate ion (MnO4−) across the same side of the alkene π bond, forming a cyclic manganate ester intermediate. Next, the hydrolysis of the cyclic ester with water gives a cis-diol...

C–C Bond Formation: Aldol Condensation Overview 01:10

13.5K

Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.

Figure 1. The general aldol addition reaction of aldehydes.
Aldol addition reactions are reversible and are of two types: self-addition and crossed-addition. Combining two identical carbonyl compounds is called...

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation 01:22

3.8K

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview 01:27

1.7K

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.

The radical reaction is initiated by a single electron transfer from metals like sodium and magnesium to a spin-paired molecule like aldehydes or ketones to generate a ketyl—a radical anion. The ketyl has a radical character on the carbon atom and a charge...

Aldehydes and Ketones with Alcohols: Hemiacetal Formation 01:19

5.7K

Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.

As alcohols are poor nucleophiles, the formation of hemiacetals is very slow under neutral conditions. The reaction rate is enhanced by using either basic or acidic reaction media.
The acid catalyst, such as sulfuric...