# 20.4 Amines and amides  (Page 3/5)

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The reaction between amines and carboxylic acids to form amides is biologically important. It is through this reaction that amino acids (molecules containing both amine and carboxylic acid substituents) link together in a polymer to form proteins.

## Proteins and enzymes

Proteins are large biological molecules made up of long chains of smaller molecules called amino acids. Organisms rely on proteins for a variety of functions—proteins transport molecules across cell membranes, replicate DNA, and catalyze metabolic reactions, to name only a few of their functions. The properties of proteins are functions of the combination of amino acids that compose them and can vary greatly. Interactions between amino acid sequences in the chains of proteins result in the folding of the chain into specific, three-dimensional structures that determine the protein’s activity.

Amino acids are organic molecules that contain an amine functional group (–NH 2 ), a carboxylic acid functional group (–COOH), and a side chain (that is specific to each individual amino acid). Most living things build proteins from the same 20 different amino acids. Amino acids connect by the formation of a peptide bond, which is a covalent bond formed between two amino acids when the carboxylic acid group of one amino acid reacts with the amine group of the other amino acid. The formation of the bond results in the production of a molecule of water (in general, reactions that result in the production of water when two other molecules combine are referred to as condensation reactions). The resulting bond—between the carbonyl group carbon atom and the amine nitrogen atom is called a peptide link or peptide bond. Since each of the original amino acids has an unreacted group (one has an unreacted amine and the other an unreacted carboxylic acid), more peptide bonds can form to other amino acids, extending the structure. ( [link] ) A chain of connected amino acids is called a polypeptide. Proteins contain at least one long polypeptide chain.

Enzymes are large biological molecules, mostly composed of proteins, which are responsible for the thousands of metabolic processes that occur in living organisms. Enzymes are highly specific catalysts; they speed up the rates of certain reactions. Enzymes function by lowering the activation energy of the reaction they are catalyzing, which can dramatically increase the rate of the reaction. Most reactions catalyzed by enzymes have rates that are millions of times faster than the noncatalyzed version. Like all catalysts, enzymes are not consumed during the reactions that they catalyze. Enzymes do differ from other catalysts in how specific they are for their substrates (the molecules that an enzyme will convert into a different product). Each enzyme is only capable of speeding up one or a few very specific reactions or types of reactions. Since the function of enzymes is so specific, the lack or malfunctioning of an enzyme can lead to serious health consequences. One disease that is the result of an enzyme malfunction is phenylketonuria. In this disease, the enzyme that catalyzes the first step in the degradation of the amino acid phenylalanine is not functional ( [link] ). Untreated, this can lead to an accumulation of phenylalanine, which can lead to intellectual disabilities.

## Kevlar

Kevlar ( [link] ) is a synthetic polymer made from two monomers 1,4-phenylene-diamine and terephthaloyl chloride (Kevlar is a registered trademark of DuPont). Kevlar’s first commercial use was as a replacement for steel in racing tires. Kevlar is typically spun into ropes or fibers. The material has a high tensile strength-to-weight ratio (it is about 5 times stronger than an equal weight of steel), making it useful for many applications from bicycle tires to sails to body armor.

The material owes much of its strength to hydrogen bonds between polymer chains (refer back to the chapter on intermolecular interactions). These bonds form between the carbonyl group oxygen atom (which has a partial negative charge due to oxygen’s electronegativity) on one monomer and the partially positively charged hydrogen atom in the N–H bond of an adjacent monomer in the polymer structure (see dashed line in [link] ). There is additional strength derived from the interaction between the unhybridized p orbitals in the six-membered rings, called aromatic stacking.

Kevlar may be best known as a component of body armor, combat helmets, and face masks. Since the 1980s, the US military has used Kevlar as a component of the PASGT (personal armor system for ground troops) helmet and vest. Kevlar is also used to protect armored fighting vehicles and aircraft carriers. Civilian applications include protective gear for emergency service personnel such as body armor for police officers and heat-resistant clothing for fire fighters. Kevlar based clothing is considerably lighter and thinner than equivalent gear made from other materials ( [link] ).

In addition to its better-known uses, Kevlar is also often used in cryogenics for its very low thermal conductivity (along with its high strength). Kevlar maintains its high strength when cooled to the temperature of liquid nitrogen (–196 °C).

The table here summarizes the structures discussed in this chapter:

## Key concepts and summary

The addition of nitrogen into an organic framework leads to two families of molecules. Compounds containing a nitrogen atom bonded in a hydrocarbon framework are classified as amines. Compounds that have a nitrogen atom bonded to one side of a carbonyl group are classified as amides. Amines are a basic functional group. Amines and carboxylic acids can combine in a condensation reaction to form amides.

## Chemistry end of chapter exercises

Write the Lewis structures of both isomers with the formula C 2 H 7 N.

What is the molecular structure about the nitrogen atom in trimethyl amine and in the trimethyl ammonium ion, (CH 3 ) 3 NH + ? What is the hybridization of the nitrogen atom in trimethyl amine and in the trimethyl ammonium ion?

Trimethyl amine: trigonal pyramidal, sp 3 ; trimethyl ammonium ion: tetrahedral, sp 3

Write the two resonance structures for the pyridinium ion, C 5 H 5 NH + .

Draw Lewis structures for pyridine and its conjugate acid, the pyridinium ion, C 5 H 5 NH + . What are the geometries and hybridizations about the nitrogen atoms in pyridine and in the pyridinium ion?

Write the Lewis structures of all isomers with the formula C 3 H 7 ON that contain an amide linkage.

Write two complete balanced equations for the following reaction, one using condensed formulas and one using Lewis structures.

Methyl amine is added to a solution of HCl.

${\text{CH}}_{3}{\text{NH}}_{2}+{\text{H}}_{3}{\text{O}}^{+}\phantom{\rule{0.2em}{0ex}}⟶\phantom{\rule{0.2em}{0ex}}{\text{CH}}_{3}{\text{NH}}_{3}{}^{+}+{\text{H}}_{2}\text{O}$

Write two complete, balanced equations for each of the following reactions, one using condensed formulas and one using Lewis structures.

Ethylammonium chloride is added to a solution of sodium hydroxide.

Identify any carbon atoms that change hybridization and the change in hybridization during the reactions in [link] .

CH 3 C H = C HCH 3 ( sp 2 ) + Cl $⟶$ CH 3 C H(Cl)H(Cl)CH 3 ( sp 3 );
2 C 6 H 6 ( sp 2 ) + 15O 2 $⟶$ 12 C O 2 ( sp ) + 6H 2 O

Identify any carbon atoms that change hybridization and the change in hybridization during the reactions in [link] .

Identify any carbon atoms that change hybridization and the change in hybridization during the reactions in [link] .

the carbon in CO 3 2− , initially at sp 2 , changes hybridization to sp in CO 2

Why does carbonic acid don't react with metals
Why does carbonic acid don't react with metal
sample of carbon-12 has a mass of 6.00g. How many atoms of carbon-12 are in the sample
a sample of carbon-12 has a mass of 6.00g. How many atoms of carbon-12 are in the sample
an object of weight 10N immersed in a liquid displaces a quantity of d liquid.if d liquid displaced weights 6N.determine d up thrust of the object
how human discover earth is not flat
We don't fall off. If set off in any direction in a straight line and keep going. You'll end up back where you started.
earth is spherical
Unique
Also, every other planet is spherical as that is the most energy efficient shape. gravity pulls equally on all areas. Sphere.
what is an ion
an atom that loses or gains an electron. Atoms normally have the same number of protons and electrons, therefore there is no charge as each + cancels out each -. When an atom loses an electron, it has more protons that electrons. Therefore the ion is called positive.
When an atom gains electrons it has more of them than protons. Therefore the ion is negative. You cannot change the number of protons as this results in a different element.
Gaining or losing electrons is based around the octet rule. 8 electrons in the outer shell is the most stable electron configuration (for the first three rows in the periodic table. After that it gets confusing so don't worry) So all atoms want to achieve this configuration.
Wat is chemical bonding
how to determine the number of atoms and the mass of zirconium, silicon, and oxygen found in 0.3384 mol of zircon4
what is a catalyst
A substance that speeds up the rate of a given reaction but does not react with any reactants
Brandon
something that speeds up a chemical reaction without being used up itself. It lowers the activation energy
something that speed up a chemical reaction without its self been used
Zainab
Faraday's first law of electrolysis state that...
the mass of a substance librated during electrolysis is directly proportional to the quantity of electricity passing through the electrolyte
Zainab
nice
Owolabi
greeaat
Abdul
another question
Owolabi
ys
Abdul
good
olanrewaju
gud one pls write it mathematically
Lekan
How can ionic bonds dissociate in aqueous solution
Because of the polarity of both ionic compounds and water the ionic compound will dissolve as "like dissolves like", and the molecule forms bonds with the water.
Claud
are all aqueous solutions water contained?
blossom
No, but a lot are.
Claud
it dissociate when d metal is combined wit oxygen
Lekan
I wanna understand more about isomers
Isomers are essentially the same molecules of one particular substance, except with different bonding points along the molecule. if you want a better example, look up xylene, p-xylene, and m-xylene. isomers are more for organic chemistry
Aaron
what is catenation
The property of carbon to form long chain with other atom!
Lareb
hydrocarbons can be classified as..1.Aliphatic compounds 2.cyclic compounds.under aliphatic compounds there are two types saturated hydrocarbons(alkanes) and unsaturated hydrocarbons(alkenes and alkynes).
thanks but i have also heard of aromatic hydrocarbons
emmanuel
so am kinda confused
emmanuel
how
Emmanuel
hydrocarbons are classified into 2 namely: aliphatic compound and aromatic compound
Mgbachi
aliphatic compound and aromatic compound
Mgbachi
hello i have big problems in understanding organic chemistry
what are the main types of hydrocarbon
emmanuel
I'm not exactly sure what you mean by 'main types' but I think you should be talking about aliphatic and cyclic hydrocarbons
blossom
What's the difference?
Claud