Organic Nitrogen compounds

What are the main types of nitrogen containing organic compoundsnitrogen-containing

Amines, Amino Acids, Nitriles, Acid Amides

Amines structure

R-NH2

Amino Acids structure

Nitriles structure

R-CN

Acid Amides structure

Amines are compounds derived from ________ in which one or more of the hydrogen atoms are substituted by an __________

ammonia, alkyl group/s

primary amine example

methylamine

secondary amine

dimethylamine

tertiary amine

trimethylamine

methylamine structure

dimethylamine structure

trimethylamine structure

(all (methyl, dimethyl) of them have a lone pair of electrons on N)

The organic equivalents of the ammonium ion are the quaternary ammonium salts containing the ion ____

R4N+

the ammonium ion structure

ammonia structure

How did the ammonium ion get 4 Hs?

The H came in as a H+ and formed a dative covalent bond with nitrogen

tetramethylammonium chloride structure

The biochemically important species acetylcholine is a __________ __________ ____

quaternary ammonium ion

acetylcholine structure

What are the 3 ways to prepare amines

1. Substitution in Haloalkanes

2. Reduction of Nitrobenzene

3. Reduction of Nitriles

Substitution in Haloalkanes Reagents:

NH3

Substitution in Haloalkanes Conditions:

Ethanol is the solvent, HUP

In Substitution in Haloalkanes, why must the NH3 be in ethanol and not water?

NH3 reacts with water and looses its lone pair:

NH3 + H2O = N+H4 + OH-

What type of reaction is Substitution in Haloalkanes

Substiution

What kind of mechanism is Substitution in Haloalkanes

Nucleophilic

the 4 steps in Substitution in Haloalkanes Equations

1. Forming Ethylamine

2. Forming Diethylamine

3. Forming Triethylamine

4. Forming Tetraethylammonium Bromide

Substitution in Haloalkanes Step 1 (Forming Ethylamine)

Ch3CH2Br + N:H3 = CH3CH2N:H2 +HBr

Substitution in Haloalkanes Step 2 (Forming Diethylamine)

CH3CH2Br + CH3CH2N:H2 =(CH3CH2)3N:H N + HBr

Substitution in Haloalkanes Step 3 (Forming Triethylamine)

CH3CH2Br + (CH3CH2)3N:H = (CH3CH2)3N: +HBr

Substitution in Haloalkanes Step 4 (Forming Tetraethylammonium Bromide)

CH3CH2Br + (CH3CH2)3N: = (CH3CH2)4N+ + Br-

Reduction of Nitrobenzene Reagents:

PACKET

Reduction of Nitrobenzene Conditions:

HUR, Tin and Conc HCl

Reduction of Nitrobenzene equation

Reduction of Nitrobenzene, the actual product formed is C6H5N+H3 as the phenylamine reacts with the ____ of the acid (HCl), to free the amine _____ is then added, equation _____________________

H+, NaOH

Appratus for reducing nitrobenzene to phenylamine by refluxing with tin and hot conc HCl

Reduction of Nitriles, Primary amines can be formed by the reduction of a nitrile using what 3 things

1. LithiumAluminium hydride,LiAlH4 (anhydrous)

2. Hydrogen and a Nickel Catalyst

3. Sodium and ethanol (anhydrous)

what does anhydrous mean

no water

formula of Lithium aluminium

LiAlH4

Reduction of Nitriles equations

CH3CN + 4[H] = CH3CH2NH2

CH3CH2CN + 4[H] = CH3CH2CH2NH2

CH3CH2CH2CN +4[H] = CH3CH2CH2CH2NH2

(butanenitrile to butylamine)

The ____ _____ on the nitrogen atom results ion amines and ammonia having similar chemical behaviour

lone pair

A amine is able to accept a proton just like ammonia, and is therefore a ____-_____ base

Bronsted-Lowry

Ethylamine + HCl equation and what is this a example of

CH3CH2NH2 + HCl = CH3CH2N+H3 Cl-

amines as a base

The free amine from CH3CH2NH2 + HCl = CH3CH2N+H3 Cl-may be regenerated by adding sodium hydroxide to a solution of the ethylammonium chloride, equation:

CH3CH2N+H3 Cl- + NaOH = CH3CH2NH2 + H2O +NaCl

protonation of NH2.C6H4.COO.CH2CH2N.(CH2CH3)2

Make NH2 into N+H3

Which is the stronger base, methylamine(CH3NH2) or phenyl amine (benzen —NH2)

CH3NH2 bc the lone pair on N in phemylamine is drawn into the delocalised pi ring, decreasing the electron density of the lone pair.

In CH3NH2 the methyl group pushes electrons onto the N, incrThe easing the electron density of the lone pair on N

The presence of the lone pair on the nitrogen atom of amines allows them to act as _________

nucleophiles

The acylaction reaction between a acyl chloride and a amine shows the nucleophilic behaviour, equation:

ethylamine +ethanoyl chloride = N-ethyl ethanamide + hydrogen chloride

CH3CH2N:H2 + CH3COCl = CH3CONH(CH2CH3) + HCl

(positive dipole on C on COCl)

A polymanide can be formed from the reacton between a ________ or __________ and a diamine

di-acid, diacyl chloride

Equation for the formation of the polymer Nylon-6,6 from the reaction between hexane-1,6-dioic acid and 1,6-diaminohexane

Example of a _____ being formed from a di-acid (or diacyl chloride) and diamine

what kind of reaction:

condensation reaction

Why is the polymer called Nylon-6,6

6 carbons in each of the monomers

What acts as nucleophiles in the formation of the polymer Nylon-6,6 from the reaction between hexane-1,6-dioic acid and 1,6-diaminohexane

the amine functional groups

The raw product of the polymerisation reaction is of little _________ use. However pulling on the ends of a sample aligns the polymer chains; ____________bonding between chains then gives a degree of crystallinity similar to that of silk

comercial, hydrogen

uses of nylon:

stockings, rope, twine, velcro

Nylon is often blended with other fibres to increase their _____ resistance

wear

Amino Acids are molecules which contain both the basic ____ group and the acidic ____ group

-NH2, -COOH

The monomer units of amino acid make up the natural polyamide polymers called ______

proteins

Almost all of the naturaly occuring amino acids are _______ ____

alpha-amino acids

Why are they called alpha amino acids

bc the amino group is attached to the aplha carbon of the carboxylic acid (2HN-C-COOH)

The Amino acid ______-_______ is a neurotransmitter found in nerve synapses in the brain

gamma- aminobutanoic acid ( or 4-aminobutanoic acid)

Amino Acids have ____ melting points and are ______ in water

high, soluble

In both solid and solution state, amino acids exist as _________ and can ____ with itself

zwitterions, react

what are zwitterions

a molecule with both a positive and a negative charge, yet with an overall neutral charge

Depending on the nature of the ___ ____, amino acids can be neautral, basic or acidic

R group

Is glutamic acid acidic or basic in water

acidic (NH2 AND COOH cancel out, but then the added COOH)

Is alanine acidic or basic in water

neutral

Is lysine acidic or basic in water

basic

Amino acids can undergo condensation reactions to form substituted amides

The resulting OC-NH bond is known as a ____ ___

peptide link

The condensation reaction between alanine and glycine

what kind of molecule does it form ( and its structure)

diapeptide

When using amino acids __ the ends, not polymerisation

close

what is a diapeptide

a molecule formed by two amino acids linked together by a peptide bondCH

Chains containing more than 20 amino acids are called __________

polypeptides

Amino acids will undergo the typical reactions of ________amines and _______ acids

primary, carboxylic

The carboxylic acid group in a amino acid will react with a base to form a _______

salt

The carboxylic acid group in a amino acid will react with a alcohol to form a _____

ester

equation of glycine (2N-CH2-COOH) with sodium hydroxide solution

H2N-CH2-COOH + NaOH → H2N-CH2-COO-Na + H2O. 

Equation of alanine with ethanol

2HN-C(CH3)H-COOH + CH3CH2OH = H2N-C(CH3)H-COO-CH2CH3 +H2

Equation of alanine with aqueous potassium carbonate

The _______ group in amino acids undergo typical reactions as a base and as a nucleophile

amine

glycine with dilute HCl

glycine (2HN-CH2-COOH)

what is his a example of

2HN-CH2-COOH + HCl(aq) = COOH—CH2—N+H3 Cl-

reaction as a base

Glycine with chloromethane

glycine (2HN-CH2-COOH)

what is his a example of

2HN-CH2-COOH + CH3Cl = H3C-NH-CH2-COOH + HCl

reaction as a base

Mechanism of glycine with chloromethane

glycine (2HN-CH2-COOH)

Polypeptides can be hydrolysed using _______ _______ ____ like hydrichloric acid.

aqueous mineral acids

what is a mineral acid

inorganic acids ( doesnt include cardoesn’tbon)

Hydrolysis of polypeptide reagents:

PACKET

Hydrolysis of polypeptide conditions:

HUR for 24 hours, 6mol/dm³ HCl

When dipeptides are hydrolysed, what do they go into

2 amino acids

Hydrolysis of dipeptide phe-ala

dipeptide phe-ala + H2O + 2HCl =