Nitrogen compounds
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How does the amine group act as a base?
The lone pair of electrons on the nitrogen can accept a H+ ion to form an an ammonium salt.
How do amines react with mono-basic, di-basic and tri-basic acids?
• Mono-basic: The NH₂ accepts the H+ ion to form NH₃+. The negitively charged part of the acid then forms an ionic bond. e.g. CH₃NH₃+Cl- • Di-basic: 2 moles of the reactant amine are needed. An ionic bond between the NH₃+ and the negitive ion from the acid is formed. 2 moles of the product salt are also formed. e.g. (CH₃NH₃+)₂SO₄²⁻ • Tri-basic. 3 moles of the reactant amine are needed. An ionic bond between the NH₃+ and the negitive ion from the acid is formed. 3 moles of the product salt are also formed. e.g. (CH₃NH₃+)₃PO₄³⁻
What factor(s) effect the ability of an amine to act as a base?
The avalibility of the lone pair to accept a H+ ion
Which amines act as the weakest bases?
Aromatic amines. The lone pair on the nitrogen delocalises into the ring, making the lone pair very inaccessible.
Which amine acts as a moderately strong base?
Ammonia. There is no aromatic ring so the lone pair can’t delocalise, making it avalible.
Which amines act as the strongest bases?
Amines with a carbon chain. The carbon chain pushes the electrons towards the nitrogen, making them readily avalible.
What is the 2 step process to form an aliphatic amine?
• Excess ammonia, dissolved in ethanol, reacts with a haloalkane to form to form an ammonium-halogeno salt. • The amine is then formed from this salt. The salt is reacted with NaOH to form the amine. The halogen reacts with the sodium to form an ionic compound. • The OH from the hydroxide reacts with the H+ released by the NH₃+ to make water. CH₃Cl + :NH₃ -> CH₃NH₃+Cl- CH₃NH₃+Cl- + NaOH -> CH₃NH₂ + NaCl + H₂O The equations above are for forming a primary amine. When forming a secondary or tertiary amine, the amine itself replaces the haloalkane.
• How is an aromatic amine formed? • What reagents and conditions are needed? • How many reducting agents, [H], should be present in the overall equation?
• The reduction of nitrobenzene. • Concentrated hydrochloric acid, tin catalyst and reflux • 6 [H] is needed to balance the equation • 2 moles of water are also formed
What is the general formula of an amino acid?
RCH(NH₂)COOH
What is a zwitterion?
At the isoelectric point, the amino acid reacts with itself. The H on the OH bonds to the nitrogen. The nitrogen gains a + charge, the oxygen gains a - charge.
What is meant by isoelectric point?
The pH at which an amino acid can act as a zwitterion
What happens to a zwitterion when the pH decreases?
• When the pH decreases, more H+ ions are avaliable. • Hydrogens are added to the molecule. Any O- groups become OH groups. • Any COO- groups become COOH groups. • A positive ion is formed as the NH₃+ parts are unchanged.
What happens to a zwitterion when the pH increases?
• H+ ions are removed from the molecule. • Any NH₃+ groups become NH₂ groups. • Any COOH groups become COO- groups. • A negative ion is formed.
What product(s) formed when an amino acid reacts with an acid?
• Acid protonates the NH₂ group, forming an NH₃+ • The X- ion forms an ionic bond with the NH₃+, forming an ammounium salt
What product(s) are formed when an acid reacts with a strong base?
A carboxylate salt (COO- X+) and water is formed
• What product(s) are formed when an amino acid reacts with an alcohol? • What is the type of reaction?
• Ester and water • Condensation reaction
What is the definition of a chiral carbon?
A carbon with 4 different groups bonded to it
What is the definition of superimpose?
Place 2 molecules over another and they are exactly the same
How are amino acids linked to chirality?
All amino acids have at least 1 chiral carbon
How do you draw the optical isomers of a molecule with 2 chiral carbons?
• Isomer 1-> Isomer 2 is a full mirror image of isomer 1 • Isomer 2 -> Isomer 3 is a mirror image of the top carbon in isomer 1. Keep the bottom carbon the same as isomer 1. • Isomer 3 -> Isomer 4 is a mirror image of the bottom carbon in isomer 1. Keep the top carbon the same as isomer 1.
What is the definition of a condensation reaction?
When small molecules join together to form a larger molecule with the loss of another small molecule (H₂O or HCL)
What is the ester link?
RCOOR
To form a condensation polymer, what reagents are needed?
• 1 monomer, with both a COOH/COCl and OH group • 2 monomers, with both a di-carboxylic acid OR di-acyl chloride and a diol
At the end of any condensation polymerisation reaction, what must be added to the equation?
(2n-1) H₂O