厦门大学化学化工学院：《有机化学》课程教学资源（授课教案）第十二章 胺类 Amines

十肜 Nines (CHH2oN2

第十二章 胺 类 Amines

a Amines are organic derivatives of o ammonia in the same way that e alcohols and ethers are organic E. derivatives of water HoO ROH RoO Water alcohol ether NH RNHo ron R2N rd ammonia amines

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Amines are organic derivatives of ammonia in the same way that alcohols and ethers are organic derivatives of water. H 2O ROH R 2 O NH 3 RNH 2 R 2NH R 3 N Wa t e r a l c o h o l e t h e r am m onia amines

121胺的结构和命名 Structure and nomenclature of amines

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 12.1 胺 的结构和命名 Structure and Nomenclature of Amines

Structure Amines are classified as primary(RNH2) secondary(R2NH), or tertiary(R3N) Depending on the number of organic substituents attached to nitrogen CH3NH2 (CH32NH (CH33N a methylamine dimethylamine trimethylamine primary secondar tertiary 伯胺(一级胺)仲胺(二级胺)叔胺(三级胺)

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Structure Amines are classified as primary (RNH 2 ), secondary (R 2NH), or tertiary (R 3N), depending on the number of organic substituents attached to nitrogen. CH 3NH 2 ( C H 3 ) 2NH ( C H 3 ) 3 N m ethylamine d i m ethylamine trimethylam ine pr i m a ry s e c o n d a ry t e rt i a ry 伯胺 (一级胺) 仲胺 (二级胺) 叔胺 (三级胺 )

Note g-Note that this usage of the terms primary, secondary, and tertiary is different from our previous usage. e a When we speak of a tertiary alcohol or alkyl halide, we refer to the degree of substitution at the alkyl carbon atom a When we speak of a tertiary amine, however, we refer to the degree of substitution at the nitrogen atom

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Note „ Note that this usage of the terms primary, secondary, and tertiary is different from our previous usage. „ When we speak of a tertiary alcohol or alkyl halide, we refer to the degree of substitution at the alkyl carbon atom. „ When we speak of a tertiary amine, however, we refer to the degree of substitution at the nitrogen atom

CH CH CH CH OH CH3-N CH3C—NH CH CH CH 3 tert-Butyl alcohol Trimethylamine tert-Butylamine (a tertiary alcohol)(a tertiary amine)(a primary amine e In secondary and tertiary amines the alkyl groups may be the same or different (CH3 CH22NH CH3 CH2NHCH3 CH 3 CH CH

Organic Chemistry Organic Chemistry Xiamen Xiamen University University CH 3 C CH 3 CH 3 OH CH 3 C CH 3 CH 3 CH 3 N NH 2 CH 3 CH 3 tert-Butyl alcohol Trimethylamine tert-Butylamine (a tertiary alcohol) (a tertiary amine) (a p rimary amine) In secondary and tertiary amines, the alkyl groups may be the same or different. (C H 3CH 2 ) 2NH CH 3CH 2NHCH 3 N CH 3 N CH 3 CH 3

3 Compounds with four groups attached to nitrogen are also known, but the nitrogen atom must carry a positive Er charge. Such compounds are called quaternary ammonium salts R + R一N-RX 季铵 R A quaternary ammonium salt

Organic Chemistry Organic Chemistry Xiamen Xiamen University University „ Compounds with four groups attached to nitrogen are also known, but the nitrogen atom must carry a positive charge. Such compounds are called quaternary ammonium salts. R N R R R X A q uaternary am m onium salt 季铵盐

Nomenclature of Amines Primary amines are named in the IUPAC system in several ways depending on their structure. For simple amines, the suffix -amine is added to the name of the alkyl substituent. g Alternatively the suffix -amine can be used in place of the final -e in the name of the parent compound

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Nomenclature of Amines „ Primary amines are named in the IUPAC system in several ways depending on their structure. For simple amines, the suffix -amine is added to the name of the alkyl substituent. „ Alternatively, the suffix –amine can be used in place of the final – e in the name of the parent compound

CH I CH3 -C-NH2 NH 2 CH tert-butylamine Cyclohexylamine CH NH2 己NH -NH2 CH o 1, 4-Butanediamine 4, 4-Dimethylcyclohexanamine

Organic Chemistry Organic Chemistry Xiamen Xiamen University University CH 3 C CH 3 CH 3 NH 2 NH 2 tert-Butylamine C yclo hexylamine NH 2 NH 2 NH 2 CH 3 CH 3 1,4 - B utaned iam i n e 4,4 - D i methylcycl ohex anam ine

An-NH2 group when not the principal group, is named by the prefix amino CO,H HoN- COH NH2 NH2 2-Aminobutanoic acid 2. 6-Diaminobenzoic acid NH 4-Amino-2-butanone

Organic Chemistry Organic Chemistry Xiamen Xiamen University University An -NH 2 group, when not the principal group, is named by the prefix amino-. CO 2 H NH 2 H 2 N CO 2 H O NH 2 2- A m i n o b utanoic acid NH 2 2,6-Di a m i n o b enzo ic acid 4- A m i n o-2-butano n e