Amines And Amides Edith, Aaron and Clark

After this class, you will... tell the different types of amines recognize the differences between amines and amides know the properties of amines and amides

Amines Organic compounds which contain a lone pair of nitrogen (N) Organic bases which react with acids Have “fish—like odor” Methylamine and 3—D model

Review: Functional group Groups of atoms or bonds which determine the special manners of substances in chemical reactions

Amides Compounds with the functional group RnE(O)xNR'2 R and R' refer to H or organic groups most common are "organic amides" (n = 1, E = C, x = 1)---RCNR NH 2 —CO---NH 2 Organic amidesulfonamidephosphor amide

Amides We can also say, compounds with the nitrogen atom which attach to a carbonyl of R–CO–NR′R″ Carbonyl: a group which the carbon atom is double--bonded by the oxygen atom

How to tell amines and amides? If we only know the chemical formulas… Tell the functional group which substituents attach to Amines---NH 2 group Amides---CONH 2 group

Examples 1 Amines: CH 3- CH 2 -NH 2 Amides: CH 3 -CONH 2

Practice 1 CH3-CH2-CH2-CH2-CONH2 Amide H2N-CH2-CH2-CH2-NH2 Amine

How to tell amines and amides? If we only know the names of substances… Tell the prefix or suffix of the subtances Amines---prefix --- “amino” ---suffix --- “amine” Amides---suffix --- “amide”

Examples 2 1,4—diaminobutane Amine Hexanamide Amide

Practice 2 2—aminopentane Amine 3,3—dimethylbutanamide Amide

Four types of amines Before we begin talking about new knowledge, we will review a little more… Alkyl group Aromatic ring

Alkyl group: a hydrocarbon lacking a hydrogen (C n H 2n+1 )

Aromatic Ring Aromatic means “fragrant” It contains benzene

Four types of amines Ammonia=NH 3 Primary Amines: one of the three H atoms is replaced by an alkyl or an aromatic group (contains at least one C 6 H 6 ) Important: Methylamine--CH 3 NH 2

Secondary amines: have two organic substituents, bound to N together with one hydrogen—it means attaching with single bond If one of the substituent is double- -bond, then there is no hydrogen bond Important: dimethylamine

Tertiary amines: all three hydrogen atoms are replaced by organic groups Important: Triphenylamine---(C 6 H 5 ) 3 N

Cyclic amines: either secondary or tertiary amines Important: Aziridines

Naming Amines There are several ways to name amines we'll only talk about the basics. The –e in the alkane name of the longest chain is changed to –amine. –Example: ethanamine is the amine derived from ethane

Naming Amines We use a number to indicate the location on the parent (longest) chain: –Example: 2-propanamine means the nitrogen is on the second carbon of a propane

22 Naming Amines In secondary and tertiary amines we use prefix “N” to indicate the substituents attached to the nitrogen. –Example: N-Methyl-2-butanamine means a methyl is attached to the nitrogen

Classification of Amides The classification of amides is the same as that of amines. Primary amides:1 H is replaced Secondary amides:2 H are replaced Tertiary amides:3 H are replaced

Naming Amides The naming of amides is also similar to naming amines, except that: –The suffix for amides is “-amide” Example: Propanamide –The parent chain contains R group and C=O. Example: N-propylethanmide

Exercises Draw: –N,N-Dimethyl-1-propanamine –N,N-Dimethylpropanamide

Chemical properties of Amines contain basicity easy to form salts if amines react with acids

Uses of Amines Primary amines are used to make dyes Some amines are beneficial to body, but some are really harmful, Amines are used to make amine drugs (mimic or interfere neurotransmitters)

Physical Properties of Amides Except HCONH 2 (Formamide), most compounds which contain RCONH 2 group are colourless solids Liquid amides are great solvents for both organic and inorganic compounds

Chemical properties of Amides Weak bases which compare to amines Do not have as clearly noticeable acid—base properties in water Has a greater solubility than other hydrocarbons in water---the oxygen atom can accept hydrogen bonds from water and the N-H atoms can donate H-bonds

Chemical properties of Amides it will explode when it meets fire and high temperature it will react with H 2 SO 4, and it will even explode if the reaction is extremely violent

Use of Amides industry: industrial solvents medical industry: produce vitamin, hormone and pesticide