Q.1 Draw structures for all amines of molecular formula C 4 H 11 N. Classify them as primary, secondary or tertiary amines.

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1 1 AMIES Structure lassification ontain the 2 group. primary (1 ) amines secondary (2 ) amines tertiary (3 ) amines quarternary (4 ) ammonium salts Aliphatic Aromatic methylamine, ethylamine, dimethylamine the 2 group is attached directly to the benzene ring (phenylamine) omenclature amed after the groups surrounding the nitrogen amine e.g ethylamine ( 3 ) 2 dimethylamine ( 3 ) 3 trimethylamine phenylamine (aniline) Q.1 Draw structures for all amines of molecular formula lassify them as primary, secondary or tertiary amines. Properties The presence of the lone pair in 1, 2 and 3 amines makes them... Lewis bases - they can be lone pair donors Brønsted-Lowry bases - they can be proton acceptors ucleophiles - they provide a lone pair to attack a positive (electron deficient) centre Physical properties Boiling point Boiling points increase with molecular mass. Amines have higher boiling points than corresponding alkanes because of intermolecular hydrogen bonding. Quarternary ammonium salts are ionic - exist as salts. intermolecular hydrogen bonding in amines Solubility Soluble in organic solvents. Lower mass compounds are soluble in water due to hydrogen bonding with the solvent. Solubility decreases as the molecules get heavier. hydrogen bonding between amines and water

2 Amines Basic properties Bases The lone pair on nitrogen makes amines basic. 2 > 3 Strength depends on the availability of the lone pair and thus its ability to pick up protons the greater the electron density on the, the better its ability to pick up protons this is affected by the groups attached to the nitrogen. electron withdrawing substituents (e.g. benzene rings) decrease basicity as the electron density on is lowered. 2 electron releasing substituents (e.g. 3 groups) increase basicity as the electron density is increased 3 2 draw arrows to show the electron density movement Measurement the strength of a weak base is depicted by its pk b value the smaller the pk b the stronger the base. the pk a value can also be used; it is worked out by applying pk a pk b = 14. the smaller the pk b, the larger the pk a. ompound Formula pk b omments ammonia methylamine methyl group is electron releasing phenylamine electrons delocalised into the ring strongest base methylamine > ammonia > phenylamine weakest base eactions Amines which dissolve in water produce weak alkaline solutions 3 2(g) 2 (l) 3 3 (aq) (aq) Amines react with acids to produce salts (l) l (aq) > l (aq) phenylammonium chloride This reaction allows one to dissolve an amine in water as its salt. Addition of aqueous sodium hydroxide liberates the free base from its salt l (aq) a (aq) > 6 5 2(l) al (aq) 2 (l)

3 3 ucleophilic haracter Due to their lone pair, amines react as nucleophiles with haloalkanes forming substituted amines nucleophilic substitution acyl chlorides forming -substituted amides addition-elimination aloalkanes Amines can be prepared from haloalkanes (see below and previous notes). eagent Aqueous, alcoholic ammonia onditions eflux in aqueous, alcoholic solution under pressure Product Amine (or its salt due to a reaction with the acid produced) ucleophile Ammonia ( 3 ) Equation 2 5 Br 3 (aq / alc) > Br ( or Br ) Problem The amine produced is also a nucleophile (lone pair on the ) and can attack another molecule of haloalkane to produce a secondary amine. This in turn is a nucleophile and can react further producing a tertiary amine and, eventually an ionic quarternary amine Br Br Br Br > Br ( 2 5 ) 2 diethylamine, a 2 amine ( 2 5 ) Br > Br ( 2 5 ) 3 triethylamine, a 3 amine ( 2 5 ) Br > ( 2 5 ) 4 Br tetraethylammonium bromide, a 4 salt Uses Quarternary ammonium salts with long chain alkyl groups e.g. [ 3 ( 2 ) 17 ] 2 ( 3 ) 2 l are used as cationic surfactants in fabric softening. Preparation from haloalkanes ucleophilic substitution using ammonia... see above nitriles eduction of nitriles using Li Al 4 in dry ether e.g [] > nitro compounds eduction by refluxing with tin and conc. hydrochloric acid e.g [] >

4 Amines AMI AIDS Structure Amino acids contain 2 functional groups amine 2 carboxyl Amine arboxyl They all have a similar structure - the identity of 1 and 2 vary general 2-aminopropanoic acid 2-aminoethanoic acid structure (Alanine) (Glycine) ptical Isomerism Amino acids can exist as optical isomers if they have different 1 and 2 groups optical isomers exist when a molecule contains an asymmetric carbon atom asymmetric carbon atoms have four different atoms or groups attached two isomers are formed one rotates plane polarised light to the left, one rotates it to the right glycine doesn t exhibit optical isomerism as there are two attached to the atom Zwitterions a zwitterion is a dipolar ion it has a plus and a minus charge in its structure amino acids exist as zwitterions produces increased inter-molecular forces melting and boiling points are higher a zwitterion Acid/base properties amino acids possess acidic and basic properties due to their functional groups they will form salts when treated with acids or alkalis. Basic properties react with 2 2 > 2 3 l 2 2 l > 2 3 l Acidic properties react with 2 2 > a 2 2 a > a 2 2 2

5 5 Q.2 Describe the arrangement of bonds in the amino acid 2 2 around... the atom in the 2 the atom in the the atom in the 2 What change, if any, takes place to the arrangement around the if the amino acid is treated with dilute acid? Peptide formation amino acids can join up together to form peptides via an amide or peptide link Structure PEPTIDES Sequences of amino acids joined together by peptide links 2 amino acids joined 3 amino acids joined many amino acids joined 2 3 dipeptide tripeptide polypeptide a dipeptide the peptide link ydrolysis Peptides can be broken down into their constituent amino acids by hydrolysis 2 2 > attack takes place at the slightly positive of the = the - bond next to the = is broken hydrolysis with just water is not feasible hydrolysis in alkaline/acid conditions is quicker hydrolysis in acid/alkaline conditions (e.g. a) will produce salts with l 2 will become 3 l 2 will become 3 a will become a will become

6 Amines Q.3 Draw structural isomers for the compounds produced when 2 2 ( 3 ) is hydrolysed by water 2 2 ( 3 ) 2 is hydrolysed in acidic solution 2 2 ( 3 ) is hydrolysed in alkaline solution Q.4 Write out possible sequences for the original peptide if the hydrolysis products are 1 mole of amino acid A, 1 mole of amino acid B and 1 mole of amino acid 1 mole of amino acid A, 2 moles of amino acid B and 1 mole of amino acid 1 mole of amino acid A, 1 mole of B, 1 mole of, 1 mole of D and 1 mole of E Proteins polypeptides with high molecular masses chains can be lined up with each other the = and - bonds are polar due to a difference in electronegativity hydrogen bonding exists between chains dotted lines represent hydrogen bonding

7 7 AMIDES - 2 Structure of amides omenclature White crystalline solids named from the corresponding acid (remove oic acid, add amide) 3 2 ethanamide (acetamide) phenyl propanamide - the tells you the substituent is on the nitrogen ylons are examples of polyamides. (see under polymers) Preparation Acyl chloride ammonia (see above) hemical Properties ydrolysis general reaction > 3 3 acidic soln l > 3 4 l alkaline soln. 3 2 a > 3 a 3 Identification Warming an amide with dilute sodium hydroxide solution and testing for the evolution of ammonia using moist red litmus paper is used as a simple test for amides. eduction educed to primary amines 3 2 4[] >

Amines H 3 C H. CH 2 CH 3 ethylmethylamine. Nomenclature. 1 o : RNH 2, 2 o : RR'NH, 3 o : RR'R"N, 4 o (salt) RR'R"R'"N + R = alkyl or aryl

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