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The conversion of a general nitrile to either an amide or carboxylic acid is facilitated by nitrilase. [5] [1] Below is a list of steps involved in transforming a generic nitrile compound with nitrilase: [4] The electrophilic carbon of the nitrile is subject to nucleophilic attack by one of the two SH groups on nitrilase.
The Letts nitrile synthesis is a chemical reaction of aromatic carboxylic acids with metal thiocyanates to form nitriles. The reaction includes the loss of carbon dioxide and potassium hydrosulfide. The polar basic substitution reaction was discovered in 1872 by Edmund A. Letts. [1] [2] The Letts nitrile synthesis
The classical procedure to convert a nitrile to the corresponding primary amide calls for adding the nitrile to cold concentrated sulfuric acid. [29] The further conversion to the carboxylic acid is disfavored by the low temperature and low concentration of water. RC≡N + H 2 O → RC(O)NH 2. Two families of enzymes catalyze the hydrolysis of ...
Forming aldehydes from carboxylic acid derivatives is challenging because weaker reducing agents (NaBH 4) are often very slow at reducing esters and carboxylic acids, whereas stronger reducing agents (LiAlH 4) immediately reduce the formed aldehyde to an alcohol. [10] Conversion to thioester followed by Fukuyama reduction
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group (−C(=O)−OH) [1] attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO 2 H, sometimes as R−C(O)OH with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), or hydrogen, or other groups ...
Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst: [1] RR’C=O + HCN → RR’C(OH)CN
This reaction involves the preparation of aldehydes (R-CHO) from nitriles (R-CN) using tin(II) chloride (SnCl 2), hydrochloric acid (HCl) and quenching the resulting iminium salt ([R-CH=NH 2] + Cl −) with water (H 2 O). [1] [2] During the synthesis, ammonium chloride is also produced. It is a type of nucleophilic addition reaction. Stephen ...
Many types of carbonyl compounds, including aldehydes, ketones, esters, thioesters, carboxylic acids, and amides, can be converted into enolate ions by reaction with LDA. Note that nitriles, too, are acidic and can be converted into enolate-like anions (referred to as nitrile anions).