Chapter 4 Condensation Reaction 第四章缩合反应 本章主要讨论内容 具有活泼氢的化合物与羰基化合物之间的缩合反应 用途:形成新的碳-碳键或碳-杂键
第四章 缩合反应 Chapter 4 Condensation Reaction 本章主要讨论内容： 具有活泼氢的化合物与羰基化合物之间的缩合反应 用途：形成新的碳-碳键或碳-杂键
Definition of Condensation Reaction A condensation reaction is a chemical reaction in which two molecules or moieties(functional groups) combine to form one single molecule, together with the loss of a small molecule When this small molecule is water, it is known as a dehydration reaction; other possible small molecules lost are hydrogen chloride, methanol, or acetic acid 两个及两个以上有机化合物分子通过反应,失 去一个小分子,形成一个新的较大分子;或同一分 子发生分子内反应,失去一个小分子,形成新分子 的反应,也称为缩合反应
Definition of Condensation Reaction 两个及两个以上有机化合物分子通过反应，失 去一个小分子，形成一个新的较大分子；或同一分 子发生分子内反应，失去一个小分子，形成新分子 的反应，也称为缩合反应。 A condensation reaction is a chemical reaction in which two molecules or moieties (functional groups) combine to form one single molecule, together with the loss of a small molecule. When this small molecule is water, it is known as a dehydration reaction; other possible small molecules lost are hydrogen chloride, methanol, or acetic acid
Intermolecular and intramolecular Intermolecular: When two separate molecules react, the condensation is termed intermolecular a simple exam ple is the condensation of two amino acids to form the peptide bond characteristic of proteins. This reaction example is the opposite of hydrolysis, which splits a chem ical entity into two parts through the action of the polar water molecule, which itself splits into hydroxide and hydrogen ions If the union is between atoms or groups of the same molecule the reaction is termed intramolecular condensation and in many cases leads to ring formation An example is the Dieckmann condensation, in which the two ester groups of a single diester molecule react with each other to lose a small alcohol molecule and form a B ketoester product
Intermolecular and intramolecular • Intermolecular：When two separate molecules react, the condensation is termed intermolecular. – A simple example is the condensation of two amino acids to form the peptide bond characteristic of proteins. This reaction example is the opposite of hydrolysis, which splits a chemical entity into two parts through the action of the polar water molecule, which itself splits into hydroxide and hydrogen ions. • If the union is between atoms or groups of the same molecule, the reaction is termed intramolecular condensation, and in many cases leads to ring formation. – An example is the Dieckmann condensation, in which the two ester groups of a single diester molecule react with each other to lose a small alcohol molecule and form a β- ketoester product
Section la-Functionalized alkylation a羟烷基化反应( a-hydroxyalkylation) Aldol condensation Prins, Benzoin, etc. a卤烷基化反应( a-chloroalky lation) Blanc reaction, a氨烷基化反应(a- aminoalkylation) Mannich, Pictet-Spengler, Strecker, etc
Section Iα-Functionalized alkylation • α-羟烷基化反应 (-hydroxyalkylation) – Aldol condensation, Prins, Benzoin,etc. • α-卤烷基化反应 (-chloroalkylation) – Blanc reaction, • α-氨烷基化反应 (-aminoalkylation) – Mannich, Pictet-Spengler, Strecker,etc
1.1 a-hydroxyalkylation 醇醛(酮)缩合 (Aldol condensation) 不饱和烃的α-羟烷基化反应 Prins reaction) 芳醛的α羟烷基化反应(安息香缩合) (Benzoin condensation) 有机金属化合物的羟烷基化 (a-hydroxyalkylation) Reformatsky reaction
1.1 -hydroxyalkylation • 醇醛(酮)缩合 – (Aldol condensation) • 不饱和烃的-羟烷基化反应 – (Prins reaction) • 芳醛的-羟烷基化反应(安息香缩合) – (Benzoin condensation) • 有机金属化合物的-羟烷基化 – (-hydroxyalkylation): • Reformatsky reaction