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70 Cards in this Set

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Amino Acids


What important molecules do amino acids form?

Peptides and Proteins

Amino Acids


What are the important functions of proteins?

Acts as...


- Antibodies


- Enzymes


- Hormones


- Structural proteins (ex. collagen, keratin)

Amino Acids


What is the general formula for an amino acid?

Amino Acids


What is a peptide?

A compound made from amino acids linked by peptide bonds

Amino Acids


What is the formula for a peptide bond?

Amino Acids


What is a Zwitterion?

A dipolar ionic form of an amino acid formed by the donation of a hydrogen ion from the carboxyl group to the amino group.


Since both charges are present, they cancel and there is no overall charge.

Amino Acids


What is the isoelectric point?

The pH at which an amino acid exists as a Zwitterion.

Amino Acids


Draw the formation of a Zwitterion of the amino acid Glycine.

Amino Acids


What does amphoteric mean?

Can react with both acids and bases.

Amino Acids


Draw and explain what happens when a Zwitterion is reacted with a solution that has a more acidic pH

The Zwitterion behaves as a base and accepts hydrogen ions to form a positively charged ion.

The Zwitterion behaves as a base and accepts hydrogen ions to form a positively charged ion.


Amino Acids


Draw and explain what happens when a Zwitterion is reacted with a solution that has a more alkaline pH

The Zwitterion behaves as an acid and donates hydrogen ions to form a negatively charged ion.

The Zwitterion behaves as an acid and donates hydrogen ions to form a negatively charged ion.


Amino Acids


What kind of reaction occurs when forming a dipeptide?

Condensation, you ding dong

Amino Acids


Draw the formation of a dipeptide

Amino Acids


How is it possible to form a different dipeptide from the same two amino acids?

Switch which groups you take from which


Ex. Take the COOH from Amino acid 1 and bond to the OH from Amino Acid 2 or take the COOH from Amino Acid 2 and the OH from Amino Acid 1

Amino Acids


WHAT ARE PROTEINS? (woah agressive caps lock)

Proteins are polypeptides formed from many amino acids joined by peptide bonds in a condensation reaction

Amino Acids


How are polypeptides/proteins broken down?

By hyrdrolysis - either acidic or alkaline.

Amino Acids


What are the conditions for the acid hydrolysis of a polypeptide/protein?

- Reflux


- 24 Hours


- 6mol dm^-3 HCl

Amino Acids


What are the conditions for the alkaline hydrolysis of a polypeptide/protein?

- 100°C


- NaOH (aq)

Amino Acids


Draw the reaction for the acidic hydrolysis of a polypeptide

Amino Acids


Draw the reaction for the alkaline hydrolysis of a dipeptide

Optical Isomerism


What are stereoisomers?

Species with the same structural formula but different arrangement of atoms in space.

Optical Isomerism


When does E/Z isomerism occur?

When each of the carbons on the double bond is attached to two different groups

Optical Isomerism


What is an optical isomer?

Stereoisomers that are non-superimposable mirror images of one another

Optical Isomerism


What is a chiral carbon?

A carbon with four different atoms/groups of atoms attached.

Optical Isomerism


What is the difference between optical isomers?

They are chemically identical, but rotate polarised light in opposite directions - anti-clockwise or clockwise.

Optical Isomerism


What is a racemic mixture?

A mixture containing equal amounts of each optical isomer - it does not rotate polarised light because they cancel eachother out.

Optical Isomerism


Explain how optical isomers usually exist in plants and animals.

In plants and animals, only one of the optical isomers is synthesised naturally, and only one will interact with an enzyme due to the stereospecific nature of enzymes.

Condensation Polymerisation


What is condensation polymerisation?

The joining of two monomer units with the elimination of a small molecule - Ex. H2O or HCl

Condensation Polymerisation


What does condensation polymerisation require?

Monomers with two different functional groups

Condensation Polymerisation


What are the two common condensation polymers you need to know?

Polyesters and Polyamides

Condensation Polymerisation


How are esters formed?

Carboxylic Acid + Alcohol -> Ester + Water

Condensation Polymerisation


Draw the general reaction of polysters made from two different types of monomer units - and give an example.

Example = Terylene

Example = Terylene

Condensation Polymerisation


Draw the general reaction of polysters made from one monomer unit - and give an example

Example = Poly(lactic) acid

Example = Poly(lactic) acid

Condensation Polymerisation


Name 4 uses of polyesters

1) Carpets


2) Sports clothing


3) Shirts


4) Often blended with cotton for clothing and bedding

Condensation Polymerisation


What are the properties of Polyester?

- Strong


- Resistant to stretching


- Resistant to chemical attack


- Burns Easily

Condensation Polymerisation


What are the properties and uses of poly(lactic) acid?

- Biodegradable


- Used for food and drink cartons

Condensation Polymerisation


What functional groups are required for the formation of a polyamide?

- COOH


- NH2

Condensation Polymerisation


Draw the general reaction of polyamides made from one monomer unit - and give an example

Example =Polyamide nylan-6,6

Example =Polyamide nylan-6,6

Condensation Polymerisation


Draw the general reaction of polyamides made from two monomer units - and give an example

Example = Kevlar

Example = Kevlar

Condensation Polymerisation



What are the properties and functions of Kevlar?

- Fire resistant


- High strength


- Used in protective clothing - crash helmets, bullet proof vests.

Condensation Polymerisation


What are the uses of polyamides?

- Used in clothing

Addition Polymerisation


What type of compound takes part in addition polymerisation?

Alkenes undergo addition polymerisation to produce saturated chains.

Addition Polymerisation


Describe additon polymerisation

The polymer is amde from only one type of monomer and there is no product other than the polymer.


Addition Polymerisation


Draw the general formula for additional polymerisation.

Addition Polymerisation vs Condensation


How do you know polymerisation is Addition or Condensation?

Addition


- Monomer has a C=C double bond


- The backbone of the polymer is a long chain of carbon


Condensation


- There are two monomers each with two functional groups


- There is one monomer with two functional groups


- There is an ester/amide linkage

HYDROLYSIS


Under what conditions can esters be hydrolysed under?

Acidic or Basic

HYDROLYSIS
What is formed when Polyesters are hydrolysed under Acidic conditions? 
Draw the hydrolysis of Terylene: 

HYDROLYSIS


What is formed when Polyesters are hydrolysed under Acidic conditions?


Draw the hydrolysis of Terylene:

- the monomer units of the polyester are produced 

- the monomer units of the polyester are produced

HYDROLYSIS
What is formed when Polyesters are hydrolysed under Basic conditions? 
Draw the hydrolysis of Terylene: 

HYDROLYSIS


What is formed when Polyesters are hydrolysed under Basic conditions?


Draw the hydrolysis of Terylene:

-NaOH/H2O
- The sodium salt of the carboxylic acid is produced with the OH groups 

-NaOH/H2O


- The sodium salt of the carboxylic acid is produced with the OH groups

HYDROLYSIS


Under what conditions can polyamides by hydrolysed under?

Acidic or Alkali

HYDROLYSIS
What is formed when polyamides are hydrolysed under acidic conditions?
Draw the product of acidic hydrolysis of nylon-6,6: 

HYDROLYSIS


What is formed when polyamides are hydrolysed under acidic conditions?


Draw the product of acidic hydrolysis of nylon-6,6:

A dicarboxylic acid and the
ammonium salt of the diamine
H+/H20
 

A dicarboxylic acid and the


ammonium salt of the diamine


H+/H20


HYDROLYSIS
What is formed when polyamides are hydrolysed under basic conditions?
Draw the product of basic hydrolysis of nylon-6,6: 

HYDROLYSIS


What is formed when polyamides are hydrolysed under basic conditions?


Draw the product of basic hydrolysis of nylon-6,6:

The sodium salt of the dicarboxylic acid and
the diamine
NaOH/H2O 
 

The sodium salt of the dicarboxylic acid and


the diamine


NaOH/H2O


Biodegradable Polymers


What do biodegradable polymers often have?

Chemical bonds that undergo hydrolysis

Biodegradable Polymers


Give two examples of biodegradable polymers, their origins and uses./

a) Poly(lactic) acid - lactic acid from corn starch, used for compost bags and food packaging.


b) Poly(glycolic) acid - glycolic acid from sugar cane, used for stitches

Biodegradable Polymers


What are synthetic biodegradable polyesters used for?

Thermofood trays and disposable plates, bowls and cups.

Biodegradable Polymers


What are photodegradable plastics?

Synthetic polymers designed to become weak and brittle when exposed to sunlight for prolonged periods.

Biodegradable Polymers


How can photodegradable plastics be made?

1) They are made by blending the polymer with light-sensitive additives that catalyse the breakdown of the polymer in the presence of UV radiation


2) They can be manufactured by introducing carbonyl bonds - C=O in the polymer backbone. The carbonyl bonds absorb light energy and break, fracturing the chain.

Biodegradable Polymers


What are photodegradable polymers initially converted to when exposed to light?

Waxy compounds, before being converted to CO2 and Water in the presence of bacteria.

Chirality in Pharmaceuitcal Synthesis


Explain the case study of Thalidamide

Thalidamide was prescribed to prevent morning sickness in pregnant women and was also used in cold and flu remedies.


It is chiral - one of the stereoisomers has the desired effect but the mirror image led to deformities in developing babies.

Chirality in Pharmaceuitcal Synthesis


Explain the case study of Seldane

Seldane was one of the first antihistamines.


It relieves symptoms associated with hayfever - sneezing and nasal congestion.


The 'inactive' isome caused a potentially fatal heart condition.

Chirality in Pharmaceuitcal Synthesis


What does 'pharmalogical activity' mean?

The beneficial or adverse effects of a drug on living matter.

Chirality in Pharmaceuitcal Synthesis


How do drugs and medicines work?

By interacting with proteins, nucleic acids and cell membranes.

Chirality in Pharmaceuitcal Synthesis


What determines the pharmalogical activity of the drug? and why?

The 3D structure of the drug because biological molecules have complex 3D structures that can only bind to a drug molecules in one possible way.

Chirality in Pharmaceuitcal Synthesis


Why is it beneficial to have only one isomer with the correct pharmalogical activity?

* Risks from unwanted side effects are reduced


* Drug doses are reduced


Chirality in Pharmaceuitcal Synthesis


What are the disadvantages of the seperation of racemic mixtures to get one isomer?

X Seperation techniques are difficult because the isomers have similar properties (similar melting point, boiling point and solubility)


X It is costly

Chirality in Pharmaceuitcal Synthesis


What can you use to seperate optical isomers?

Enzymes, electrophoresis and chromatography.

Chirality in Pharmaceuitcal Synthesis


What isomers can be produced in the lab?

A mixture of both optical isomers.

Chirality in Pharmaceuitcal Synthesis


What isomers are produced in nautre?

A single optical isomer is produced.

Chirality in Pharmaceuitcal Synthesis


What three ways can chiral compounds be synthesised?

1) USING ENZYMES AS BIOLOGICAL CATALYSTS


Nature is good at making single optical isomers.


If a synthetic route involving enzymes is designed, then a single isomer can be produced.


2) CHIRAL POOL SYNTHESIS


Uses the pool of naturally occuring chiral molecules within the synthetic route. the chirality of the original molecule can lead to the formation of a product that is a single, pure optical isomer. (Common starting materials for chiral pool synthesis includes natural alpha-amino acids and sugars.)


3) USE OF TRANSITION ELEMENT COMPLEXES


to produce chiral catalysts which can then transfer their chirality to synthesis a single isomer product.

Chirality in Pharmaceuitcal Synthesis


What is Ibuprofen and how does it work?

An anti-inflammatory drug that targets bone and muscle pain. It blocks messages to the brain and reduces swelling or inflammation. It relieves heache, back pain and period pain, cold and flu symptoms and arthritus.

Chirality in Pharmaceuitcal Synthesis


Describe the chirality of Ibuprofen.

It has one chiral carbon so has two optical isomers. One relieves pain more effectively than the other, but in the body the less active isomer is converted to the other forms.


This means the full dose is active.


This minimises any possible side effects.