7. polymers and life

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1

amino acids

molecules containing a basic amino group, a acidic carboxyl group and variable group

<p>molecules containing a basic amino group, a acidic carboxyl group and variable group</p>
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amphoteric

a molecule with both acidic and basic properties

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zwitterion

a molecule that’s overall neutral with both a positive and negative charge

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isoelectric point

the pH where the overall charge on the amino acid is zero so it exists as a zwitterion

both the carboxyl group and amino group are charged

<p>the pH where the overall charge on the amino acid is zero so it exists as a zwitterion</p><p>both the carboxyl group and amino group are charged</p>
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acid

conditions more acidic than isoelectric point where the -NH2 group in an amino acid is protonated

<p>conditions more acidic than isoelectric point where the -NH2 group in an amino acid is protonated</p>
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base

conditions more basic than the isoelectric point where the -COOH group in amino acid loses a proton

<p>conditions more basic than the isoelectric point where the -COOH group in amino acid loses a proton</p>
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paper chromatography

  • draw pencil line and add concentrated spot

  • place in beaker with solvent below pencil line, ass watch glass above to stop evaporation

  • substances move up with solvent separating out

  • remove paper and mark solvent front

  • identify positions of amino acids by spraying ninhydrin solution (purple) or dipping paper in a jar with iodine crystals (brown), circle spots

  • calculate Rf values

<ul><li><p>draw pencil line and add concentrated spot</p></li><li><p>place in beaker with solvent below pencil line, ass watch glass above to stop evaporation</p></li><li><p>substances move up with solvent separating out</p></li><li><p>remove paper and mark solvent front</p></li><li><p>identify positions of amino acids by spraying ninhydrin solution (purple) or dipping paper in a jar with iodine crystals (brown), circle spots</p></li><li><p>calculate Rf values</p></li></ul>
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Rf values

= distance moved by spot ÷ distance moved by solvent

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proteins

condensation polymers of amino acids, joined by peptide links

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condensation reaction

reaction between the amine group of an amino acid and a carboxylic group of another, forms a dipeptide/protein with a peptide bond

<p>reaction between the amine group of an amino acid and a carboxylic group of another, forms a dipeptide/protein with a peptide bond</p>
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polypeptide

formed when many amino acids join together to make a chain

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hydrolysis

reaction to break down amino acid, requires harsh conditions hot aqueous 6 mol dm-3 hydrochloric acid and heated into reflux for 24 hours produces ammonium salts, final mixture neutralised using a base

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primary structure

sequence of amino acids in the long chain that makes up the protein

<p>sequence of amino acids in the long chain that makes up the protein</p>
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secondary structure

peptide links can form hydrogen binds allowing the chain to from a alpha helix chain or beta pleated sheet

<p>peptide links can form hydrogen binds allowing the chain to from a alpha helix chain or beta pleated sheet</p>
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tertiary structure

extra bonds form between r groups on polypeptide chain given it a 3D shape

<p>extra bonds form between r groups on polypeptide chain given it a 3D shape</p>
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bonds in tertiary structure

all bonds between R groups

  • instantaneous dimple-induced forces, weak attractions between non polar side groups eg CH3

  • ionic interactions between charged side groups eg CO2- and NH3+

  • hydrogen bonds eg -OH, -COOH, -NH2 and -CONH2

  • disulphide bridge between thiol (-SH) groups

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DNA deoxyribonucleic acid

polymer of nucleotides that contains all the genetic information of an organism

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nucleotide

monomer of DNA made up of a phosphate group, pentose sugar (deoxyribose) and a base

<p>monomer of DNA made up of a phosphate group, pentose sugar (deoxyribose) and a base</p>
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adenine, cytosine, guanine and thymine

DNA bases

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phosphate sugar backbone

formed when nucleotides join together to make a polynucleotide chain, bonds form between a phosphate group and sugar

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RNA

polymer of nucleotides with a series of bases attached to a phosphate sugar backbone, similar to DNA but contains ribose sugar and uracil

<p>polymer of nucleotides with a series of bases attached to a phosphate sugar backbone, similar to DNA but contains ribose sugar and uracil</p>
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phosphate ester link

bound formed in condensation reaction which hold phosphate sugar back bone together, between OH groups

<p>bound formed in condensation reaction which hold phosphate sugar back bone together, between OH groups</p>
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-NH group and -OH group

groups where a condensation reaction takes place to join DNA bases to phosphate sugar back bone

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double helix

shape of DNA as it is made if 2 polynucleotide stands where the bases join them together by complementary base pairing of hydrogen bonds

<p>shape of DNA as it is made if 2 polynucleotide stands where the bases join them together by complementary base pairing of hydrogen bonds</p>
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2 hydrogen bonds

number of hydrogen bonds between adenine and thymine

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3 hydrogen bonds

number of hydrogen bonds between guanine ad cytosine

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hydrogen bonds

occur between bases where there is a polar bond with hydrogen ( H arched to anything highly electronegative like N and a lone pair of electrons is nearby to bond to like O, N or F atoms)

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self replication

DNA has to be copied for cell growth

  • hydrogen bonds break and DNA unzips

  • free nucleotides pair up with bases by complementary base pairing

  • DNA polymerase joins nucleotides together to from a polynucleotide chain

  • results on 2 identical double strands DNA

<p>DNA has to be copied for cell growth</p><ul><li><p>hydrogen bonds break and DNA unzips</p></li><li><p>free nucleotides pair up with bases by complementary base pairing</p></li><li><p>DNA polymerase joins nucleotides together to from a polynucleotide chain</p></li><li><p>results on 2 identical double strands DNA</p></li></ul>
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base codons

a triplet of bases that code from one main acid, 64 possibilities and 20 amino acids

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messenger RNA (mRNA)

single polynucleotide strand, exact reverse copy of DNA except uracil instead of thymine

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transfer RNA (tRNA)

single polynucleotide strand that’s folded to a clover shape, at one end there is a sequence of 3 bases called an anticodon which attaches to mRNA, other end there is a binding site fro an amino acid

<p>single polynucleotide strand that’s folded to a clover shape, at one end there is a sequence of 3 bases called an anticodon which attaches to mRNA, other end there is a binding site fro an amino acid</p>
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ribosomal RNA (rRNA)

polynucleotide strands attached to proteins which make things called ribosomes, largest type of RNA

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transcription

process to produce mRNA

  • hydrogen bonds break and DNA unzips revealing a small single stranded region

  • free RNA nucleotides pair up with bases by complementary base pairing

  • RNA polymerase joins nucleotides together

  • forms mRNA and DNA coils up again unaltered

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translation

process to make proteins:

  • ribosomes attach to mRNA and moves along it looking for a start codon (AUG)

  • a tRNA with the correct anticodon bases pairs to tRNA

  • peptide bond joins the polypeptide chain together

  • process continues until stop codon is reached and then the ribosome releases the polypeptide chain together

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enzyme

biological catalyst for many reactions organisms, they are proteins but can have non protein parts, area called active site where substrate binds

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lock and key

model which explains how enzymes are specific to one substrate

<p>model which explains how enzymes are specific to one substrate</p>
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optimum conditions

the narrow range of temperature and pH which enzymes work at

to high temperature and they denature, to low and they very slow

changes in pH cause them to denature

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competitive inhibitors

molecules with a similar shape to substrate they bind to enzymes and block them preventing it working

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enzyme rate of reaction

increases with substrate concentration unit It plateaus due to another factor

so is first order until its zero order unlike a uncatalysed reaction that remains first order

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enzymes rate experiments

can be measured using gas syringe, mass balance or titrations

eg potato (contains catalyse) and hydrogen peroxide produces a gas

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receptors

sites on cells where chemicals bind to and either inhibit something or trigger a series of biochemical reactions, chemicaas have to be exactly the right shape and size to fit

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molecular recognition

describes the intermolecular interaction between tow or mole molecules

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medical active

allowed due to a drug having the reconnect molecular recognition with a receptor

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pharmacophore

part of a the drug that fits into a receptor and makes it medically active

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fit of a pharmacophore depends on

  • size and shape so it can fit the receptor

  • bond formation, allowing for temporary bonds with receptor, include dipole dipole interactions, hydrogen bonds and ionic interactions

  • orientation, if they have E/Z optical isomers then only one will fit

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modification

once the pharmacophore part has been identified other parts can be changed to make it more effective or reduce side effects, eg noradrenaline (found in body) has changed to be salbutamol and isoprenaline

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optical isomers

molecules that are mirror images of each other, also called enantiomers

<p>molecules that are mirror images of each other, also called enantiomers</p>
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chiral carbon

a carbon atom which has 2 diffenert groups attached to it, so the groups have 2 possible arrangements

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optically active

optical isomers rotate plane polarised light, one rotates it clockwise, the other anticlockwise the same amount

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plane polarised light

light which only vibrates in one direction unlike normal light which vibrates in all directions

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drawing optical isomers

identify chiral carbon, this sits in the middle of the rain then there is 2 straight lines, a dash and a wedge with the functional groups

<p>identify chiral carbon, this sits in the middle of the rain then there is 2 straight lines, a dash and a wedge with the functional groups</p>
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multiple chiral centre

occurs in molecules meaning they will have multiple optical isomers

<p>occurs in molecules meaning they will have multiple optical isomers</p>
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carboxylic acids

-COOH group, CnH2nO, carboxy- / -oic acid eg ethanoic acid

weak acids as they partially dissociate in water

<p>-COOH group, CnH2nO, carboxy- / -oic acid eg ethanoic acid</p><p>weak acids as they partially dissociate in water</p>
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acid anhydride

O between C=O, CnH2n-2O3, -oic anhydride, eg ethnic anhydride

<p>O between C=O, CnH2n-2O3, -oic anhydride, eg ethnic anhydride</p>
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esters

O-C=O, CnH2nO2, -oate, eg methyl ethanoate

<p>O-C=O, CnH2nO2, -oate, eg methyl ethanoate</p>
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acyl chlorides

Cl-C=O, CnH2n-1OCl, -oyl chloride, eg ethanol chloride

carboxylic acid derivatives

easily lose their chlorine

<p>Cl-C=O, CnH2n-1OCl, -oyl chloride, eg ethanol chloride</p><p>carboxylic acid derivatives</p><p>easily lose their chlorine</p>
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amides

-C=O-NH2, CnH2n-1ONH2, -amide, eg ethanamide

<p>-C=O-NH2, CnH2n-1ONH2, -amide, eg ethanamide</p>
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aldehydes

H-C=O, CnH2nO, -al eg ethanal

a person of a carbonyl group with it at the end and a H

<p>H-C=O, CnH2nO, -al eg ethanal</p><p>a person of a carbonyl group with it at the end and a H</p>
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Ketones

-C=O, CnH2nO, -one, propanone

version of carbonyl group with it in the middle of the chain

<p>-C=O, CnH2nO, -one, propanone</p><p>version of carbonyl group with it in the middle of the chain</p>
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alcohols

-OH, CnH2n+1OH, -ol / hydroxyl eg ethanol

<p>-OH, CnH2n+1OH, -ol / hydroxyl eg ethanol</p>
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phenols

-benzene ring with a OH, RC6H4OH, -phenol, eg 3-ethylphenol

<p>-benzene ring with a OH, RC6H4OH, -phenol, eg 3-ethylphenol</p>
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primary amine

-NH2 group, CnH2n+3N, -amine / amino- eg aminoethane

<p>-NH2 group, CnH2n+3N, -amine / amino- eg aminoethane</p>
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arenes

-benzene ring, RC6H5, -benzene / phenyl- eg ethyl benzene

<p>-benzene ring, RC6H5, -benzene / phenyl- eg ethyl benzene</p>
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ethers

R-O-R’, CnH2n+2O, alkoxy-, eg methoxy ethane

<p>R-O-R’, CnH2n+2O, alkoxy-, eg methoxy ethane</p>
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carbonyl group

functional group C=O, found in aldehydes and ketones

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diol

contain 2 -OH groups

<p>contain 2 -OH groups</p>
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acid anhydrides

contain a -C=OOC=O- group, R group on each end

<p>contain a -C=OOC=O- group, R group on each end</p>
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primary amines

formed when one of the hydrogens in ammonia Is replaced with an organic group

smell fishy

basic so tested for by seeming if it runs damp red litmus paper blue

<p>formed when one of the hydrogens in ammonia Is replaced with an organic group</p><p>smell fishy</p><p>basic so tested for by seeming if it runs damp red litmus paper blue</p>
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test for amides

add acyl chloride, positive result gives white fumes and HCl gas

violent reaction and produces secondary amide

<p>add acyl chloride,  positive result gives white fumes and HCl gas</p><p>violent reaction and produces secondary amide</p>
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dative covalent bond

formed between lone pair of electrons on nitrogen and a proton, makes it a positively charged cation

<p>formed between lone pair of electrons on nitrogen and a proton, makes it a positively charged cation</p>
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secondary amide

formed when nitrogen in amide has a second R group attached, have the prefix N-alkyl-

<p>formed when nitrogen in amide has a second R group attached, have the prefix N-alkyl-</p>
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hydrolyse

process carried out to amides, either under acidic or basic conditions

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dilute acid

conditions amide heated with that produces a carboxylic acid and ammonium salt

<p>conditions amide heated with that produces a carboxylic acid and ammonium salt</p>
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dilute alkali

conditions amide heated with to produce a carboxylate ions and ammonia gas

<p>conditions amide heated with to produce a carboxylate ions and ammonia gas</p>
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dicarboxylic acids

molecules containing 2 carboxylic functional groups, end in -diotic acid

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more reactive metals

carboxylic acids react with them in a redox reaction forming salt and hydrogen gas

<p>carboxylic acids react with them in a redox reaction forming salt and hydrogen gas</p>
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carbonates

carboxylic acids react with them to form a salt, carbon dioxide and water

<p>carboxylic acids react with them to form a salt, carbon dioxide and water</p>
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neutralised

carboxylic acids with aqueous alkalies to form salta and water

<p>carboxylic acids with aqueous alkalies to form salta and water</p>
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esters

made by reacting an alcohol with a carboxylic acid, the name is a combination of the two

gives the molecule -C=OO- functional group

made in a condensation reaction releasing water

<p>made by reacting an alcohol with a carboxylic acid, the name is a combination of the two</p><p>gives the molecule  -C=OO- functional group</p><p>made in a condensation reaction releasing water</p>
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acid hydrolysis

reversible reaction which spilts an ester into a carboxylic acid and an alcohol, due under reflux and requires lots of water to push the equilibrium to the right

<p>reversible reaction which spilts an ester into a carboxylic acid and an alcohol, due under reflux and requires lots of water to push the equilibrium to the right</p>
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base hydrolysis

irreversible reaction with an easter which produces a carboxylate salt and an alcohol, done under reflux

<p>irreversible reaction with an easter which produces a carboxylate salt and an alcohol, done under reflux</p>
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acyl chloride and alcohol

a irreversible vigorous reaction that quickly produces an ester

Cl is subsituted by an oxygen, nucleophilic substitution

<p>a irreversible vigorous reaction that quickly produces an ester</p><p>Cl is subsituted by an oxygen, nucleophilic substitution</p>
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addition polymers

formed by alkenes joining together by the double bond breaking

produces unreactive chain

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condensation polymers

usually involve 2 types of monomer with a at least 2 function groups which react together forming a link losing water in the process eg natural ones like proteins or polyester and polyamides

can be hydrolysed under acidic or basic conditions to break it down

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polyamides

made form dicarboxylic acid and diamine monomers, form amide links between them when the -OH and H react releasing water

<p>made form dicarboxylic acid and diamine monomers, form amide links between them when the -OH and H react releasing water</p>
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polyesters

made from dicarboxylic acid and diol monomers, ester links are formed between -OH and H releasing water

<p>made from dicarboxylic acid and diol monomers, ester links are formed between -OH and H releasing water</p>
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87

nylon

a type of polyamide, either made from one monomer or 2 monomers

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2 monomers

nylon formed in condensation reaction between diamine and dicarboxylic acid

named by nylon-x,y where x and y are the number of carbon atoms in each monomer

<p>nylon formed in condensation reaction between diamine and dicarboxylic acid</p><p>named by nylon-x,y where x and y are the number of carbon atoms in each monomer</p>
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89

1 monomer

nylon made from monomers coating an amide and carboxylic acid which can react with themselves

named by nylon-x where x I the number of carbon atoms in the monomer

<p>nylon made from monomers coating an amide and carboxylic acid which can react with themselves</p><p>named by nylon-x where x I the number of carbon atoms in the monomer</p>
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90

mass spectrometry

used to identify organic compounds by mass

compounds are bombarded by electrons and break up into fragments

charged ions are detected and create a fragmentation pattern

<p>used to identify organic compounds by mass</p><p>compounds are bombarded by electrons and break up into fragments</p><p>charged ions are detected and create a fragmentation pattern</p>
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M peak

highest peak that tells you the mr of a molecule

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M+1 peak

very small peak with the highest mass due to carbon 13 isotope

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lost fragments

don’t show up on mass spectrometer due to been uncharted radical or unstable so break down before detected or doens’t form a positive charge easily, can be workout however by the difference between peaks

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high resolution mass spectrometers

able to give m/z values to at leats 4 decimal places, allows you to compare elements and compounds using relative atomic masses so can more accurately determine what something is

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NMR spectroscopy (nuclear magnetic resonance)

analytical technique to work out structure of molecules

a sample is placed in a string magnetic field and exposed to a range of radio wave frequencies

the nuclei absorb energy, amount depends on its environment

the pattern of absorptions gives you positions of atoms in the molecule

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carbon 13 NMR

tells you about the number and types if different carbon environments in a molecule

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high resolution proton NMR

tells you about number of hydrogen atoms in a molecule and their environments

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shielding

happens to carbon atoms due to hydrogen surrounding it, affects frequencies they absorb

<p>happens to carbon atoms due to hydrogen surrounding it, affects frequencies they absorb</p>
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chemical shift

the difference in frequencies absorbed compared to a standard substance- tetramethylsilane (TMS) has 12 hydrogens producing identical environments, produces a single peak at 0

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hydrogen environments

effected by atoms up to 3 bonds away

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