Organic

Chemistry A2
Chapter 25-30

Debra Crawford
 Thank you for downloading and reviewing my slides
 You are welcome to make changes
 Please repost the slides after you edits I would to see
your edits

 IF you have any questions or would like help in find

the answer key please email me at
d.ashelyc@yahoo.com

Debra Crawford
 Sources used in preparing this PowerPoint

 Cambridge International AS and A Level Chemistry Coursebook Second Edition by

Lawrie Ryan and Roger Norris ISBN: 978 1 107 63845 7

 Cambridge International AS and A Level Chemistry Revision Guide by Judith potter

and Peter Cann ISBN:978 1 107 61665 3

 Cambridge International AS and A Level Chemistry by Peter Cann and Peter Huges
ISBN: 978 1444 18133 3

 Revision Guide Cambridge International AS and A Level Chemistry Second Edition by

David Bevan ISBN: 978 1 4718 2940 6

 Organic Chemistry Second Edition by David Klein ISBN: 978 1 118 45228 8

 Student Study Guide and Solution Manual for Organic Chemistry Second Edition by
David Klein ISBN: 978 1 118 64795 0

 Some yahoo search images

 Meet 3 times a week for organic chemistry
 Meet once a week for a double class of lab in
preparation of paper 5

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Year plan
 Review of organic

 Spend about 3 weeks on each chapter

 Posters after chapter 28

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Review organic
chemistry from
AS year
What is organic chemistry?
 Studiesof organic molecules and reactions
 Covalent compounds
C
 Out number inorganic by 80:1 WHY?

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Types of formals
 Empirical formula
 Molecular formula
 Structural formula
 Displayed formula
 Skeletal formula
 3D displayed formula
 General formula

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Naming carbon chians
Number of carbons in chain Name
1 Meth-
2 Eth-
3 Prop-
4 But-
5 Pent-
6 Hex-
7 Hept-
8 Oct-
9 Non-
10 Dec-
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Bonding
 Sigma

 Pi

 Hybridisation of C
 sp
 sp2
 sp3
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Functional groups
 Alkanes
 Alkenes
 Halogenoalkanes
 Alcohols
 Aldehydes
 Ketones
 Carboxylic acids
 Esters

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Isomers
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Organic reaction -mechanisms
 Homolytic fission
 Heterolytic fission

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Homolytic fission
 When a covalent bond breaks by splitting the
shared pair of electrons between the two products
 Produces two free radicals, each with an unpaired
electron

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Free radical

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 Initiation
step
 Propagation step
 Termination step

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Heterolytic fission
 When a covalent bond breaks with both the shared
electrons going to one of the products
 Produces two oppositely charged ions

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Carbocation

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Electrophile
 Electron-deficient species which is therefore
attracted to parts of molecules which are electron
rich
 Positive ions or have a partial positive charge

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Nucleophile
 Electron-rich species which is therefore attracted
to parts of molecules which are electron deficient
 Nucleophile have lone pair of electrons and may
also have a negative charge

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Types of organic reactions
 Addition
 Elimination
 Substitution
 Hydrolysis
 Oxidation
 Reduction

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Addition

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Elimination and Substitution

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Hydrolysis

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Oxidation and Reduction

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Chapter 25
Benzene and its compounds
The benzene ring

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Joining of benzene
 Two ways

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Naming
 Isomerism

 Two ways to name position

 1,2,3,4,5,
 Or ortho-, meta- and para-

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Monosubstitution
 Bromobenzene
 Nitrobenzene
 Ethylbenzene
 Propylbenzen

 Phenol

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 Drawout all possible positional isomers of
C6H3Br2OH and name them.

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 When the benzene ring is the substituent

 Phenyl

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Reactions of arenes
 Electrophilic substitution with Cl/Br
 Nitration of benzene
 Alkylation of benzene

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Combustion
 Complete

 Incomplete

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Electrophilic substitution with Cl/Br
 Alkene

 Electrophilic addition
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 Arenes

 Electrophilic substitution
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Step 1 catalyst
 Warming
 Anhydrous AlCl or AlBr3 or FeBr3
3

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Nitration
 Warm 55˚C

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Friedel-Crafts reaction
 Electrophilic substitution

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Friedel-Crafts
Alkylation

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 sp3 hybridized
 NO incompatibile
2

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Frieldel-Crafts
Acylation

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Oxidation of side chain

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Hydrogenation

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Phenol
C H5OH
6
 Melting point 43˚C
 Crystalline solid

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Phenol naming
 Phenol
 Halogen
 Nitro
 Amino
 Alkyl
 Hydroxy substituent
 Aldehyde
 Ketone
 Carboxylic acid
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Acidity
 Weak acid

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 Resonance
 Induction
 Solvation effects

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Resonance

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Induction

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Solvation effect

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Reactions of phenol
 Reaction of –OH group
 Breaking O-H bond
 Substitution of OH in benzene ring

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O-H bond
 Dissolves in alkaline solutions

 Sodium

 Bases

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Esterification

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Substitution reaction

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Coupling

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Test for phenols
 Br
2

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Preparing phenols

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Uses of phenols
 Antiseptics/disinfectants
 1867 dilute solution of phenol in water

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Uses of phenols
 Analgesics
 painkilling and fever-reducing
 Willow bark (16th century)
 salicylic acid
 1893

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Chapter 26
Carboxylic Acids and Their
Derivatives
The acidity of carboxylic acids
 H+ reactes with bases to make salts
 Carboxylates
 Sodium ethanoate
 CH3COO-Na+

 Weak acid
 Most are undissociated in water

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 Relative acidities from demonstration

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Acidity and benzene

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Oxidation of two carboxylic acids
 Methanoic acid

 Ethanedionic acid

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HCOOH
 acidified dichromate(VI)

 Potassium manganite(VII)

 Fehling’s solution and Tollens’ reagent

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HOOCCOOH
 Potassium manganite(VII)

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Acyl chlorides
 -OH group of carboxylic acid is replaced with Cl

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How to make

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Why do we want arcy chlorides
 Carboxylic acid are quite unreactive

 Arcy chlorides are more reactive than carboxylic

acid

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 Intermolecular forces

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 Please explain the effects of the carboxyl group.

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Reactions
 Water
 Alcohols
 Phenols
 Ammonia
 Amines

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Water

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 Aryl
chlorides, such as chlorobenzene, will not
undergo hydrolysis

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Alcohols

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Phenols

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Ammonia

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Amines

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Reduction

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 Predictthe major product(s) for each of the
following reactions:

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Chapter 27
Organic Nitrogen Compounds
Amines
 Three classes

 Primary
 Secondary
 Tertiary

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Naming Amines
 Primary

 amine

 When not the main group amino-

 All besides halogens

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 Secondary and Tertiary

 Name each group

 If amine is not main group use N- is show that it is on

the N
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Naming

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 Draw and name
1. Cyclohexylmethylamine
2. Tricyclobutylamine
3. 2,4-Diethylphenylamine
4. 2-Methylcyclohexanamine
5. ortho-Aminobenzaldehyde

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 What is the hybridizion on N in an amine

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Intermolecular forces

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Basicity of amines
 Base is a H+ proton acceptor

N donates its lone pair to the H+ forming a co-

ordinate bond

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Delocalization Effects

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Formation of amines
 NH
3
 CN-

 Reduction

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Nucleophilic substitution
 Hot ethanolic ammonia

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 Excess ammonia must be used

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 Replacehalogen
 Cyano group

 Nitrile

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Nucleophilic substitution
 Heated under reflux

 Sodium cyanide
 Potassium cyanide

 In ethanol

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Bromine water

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Reactions as nucleophiles
 alkyl and acyl halides

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 excess of a bromoalkane, amines can be
successively alkylated, first to secondary and then
to tertiary amines
 alkylated to quaternary ammonium salts

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Reaction with nitrous acid
(nitric(III) acid)
 Nitrous acid, HNO2, is unstable

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Diazotisation

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Coupling

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Amino acids
 Amino group -NH2
 Carboxylic group –COOH

 2-amino-carboxylic acid
 RCH(NH2)COOH

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 White solids
 High melting points
 Solubility

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 Zwitterion

 Amphoteric

 Resist change in pH

 Chiral center Carbon

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Reactions of amino acids
 Acylated
 Nitrous acid
 Esterifed
 Buffers
 Reactions for
 R groups

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Peptides
 Condensation reaction

 Amino Acids
 2- dipeptide
 3 – tripeptide

 Polypeptide
 Protein

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 ORDER MATTERS

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 How many possible tripeptides can be formed
from the three amino acids Gly, Ala and Ser, if
each tripeptide contains all three amino acids?

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Amides
R and R can be alkyl, aryl or hydrogen

 Extensively hydrogen bonded

 Hδ+ atoms (on nitrogen)
 Lone pairs on N and O

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Reactions of the amides
 Preparation
 Hydrolysis
 Reduction

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Preparation

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Hydrolysis

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Reduction

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Electrophoresis
 Biochemical analysis
 Separate, identity and purify proteins

 Paper
 Gel

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 Isoelectric point (pI)

 Amino acids have zwitterionic forms

 pH where that form is most likely

 The greater the different between the buffer and pI the

further the amino acid will travel in paper electhoresis

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Finding pI

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Chapter 28
Polymerisation
Addition polymerisation

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Condensation polymerisation
 Type I
 Type II

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Synthetic polyamides
 Polyamide
 Peptide link

 -NH
2
 -COOH
 -COCl

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Kevlar

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Biochemical polymers
 Protein
 16% of the human body

 Condensation polymerization
 Unbranched
 Unique sequence of amino acids
 Sequence determined by DNA
 Particular biological function

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Protein Structure
 Primary
 Secondary
 Tertiary

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Primary
 Orderof amino acids
 Numbered from N-terminal
 Covalent bonding

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Secondary
 Three‑dimensional conformations of regions of the
protein

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a-helix
a helix forms when a portion
of the protein twists into a
clockwise spiral
 Each turn has approximately
four amino acid residues,
 Each C=O group experiences
hydrogen bonding with an N-
H group that is four residues
farther along on the chain.

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Β-pleated sheet
 Hydrogen bonding occurs between the C=O group
and N-H group of neighboring strands
 R groups (side chains) are positioned above and
below the plane of the sheet, in an alternating
pattern

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Tertiary
 Further folding of polypeptide chain

 Disulfide bridges
 Weak van der Waals’ forces
 Relatively weak hydrogen bonds
 Ionic bonds (salt bridges)

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Disulfide bridges

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Weak van der Waals’ forces

 Non-polar
 Total can be considerable

 A large proportion of amino acids

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Relatively weak hydrogen bonds

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Ionic bonds (salt bridges)
 Between side chains

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Hydrolysis of proteins

excess of
acid
alkali,
reflux
refllux
HCl NaOH

Cl–H3N+
H2N RCH
RCH
COO–Na+
COOH
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The importance of hydrogen bonding
in DNA
 Deoxyribonucleic acid
 Can copy itself
 Stores information for making proteins

 Monomers
 Nucleoside phosphates

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Nucleoside phosphates
 Sugar
 Deoxyribose
 5 membered ring
 Phosphate group

 Nitrogen-containing base
 Four types

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`

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Complementary base pairs
 A always pairs with T
 forming two hydrogen bonds between them
G always pairs with C
 forming three hydrogen bonds between them

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DNA replication
 The hydrogen bonds and van der Waals’ forces
between the base pairs in part of a DNA molecule
are broken.
 This part of the double helix unwinds.
 Nucleotide triphosphates are brought up one by
one to the separated part of the chain.
 Enzymes catalyse the polymerisation reaction..

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Polyesters

 Dicarboxylic acids
 Diols

 Acid hydrolysis of polyesters

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Terylene®
 benzene-1,4-dicarboxylic acid
 ethane-1,2-diol

 antimony(III) oxide
 280 °C

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Poly(lactic acid)
 PLA
 lactic
acid
 2-hydroxypropanoic acid

 raw material is starch from corn

 biodegradable

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Designing useful polymers
 Density

 Low-density
 High density

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Non-solvent-based adhesives
 Traditional adhesives
 Flammable
 Pollution

 Silicon bonded to
oxygen
 -Si-O-Si-

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 Thermosets

 Verystrong
 Cannot be melted
 Cannot be remolded

 Reaction is initiated by presence of moisture

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Degradable polymers
 What are problems with plastics?

 Biodegradable
 Photodegradable

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Biodegradable
 Decomposed
 By microorganisms

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Photodegradable
 C=O
 Ultraviolet

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Conducting polymers
 Conduct electricity

 Conjugated double bonds

π bonds

 One dimensional delocalized electrons

 Doping
 Adding other substances to increase conductivity
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Advantages over metals
 Not corrode
 Less dense
 Can be shaped easier

Disadvantages to metals
 Less conductive

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Polymer deductions
1. Predict the type of polymerisation reaction for a
given monomer or pair of monomers
2. Deduce the repeat unit of a polymer obtained
from a given monomer or pair of monomers
3. Deduce the type of polymerisation reaction that
produces a given section of a polymer molecule
4. Identify the monomer(s) present in a given
section of a polymer molecule.

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 Addition polymers
 C=C

 Condensation
 Linking
 Ester
 Amide

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Review
Chapters 24-28
Organic Chemistry Review
What are mechanism
 Shows the movement of electrons
 Changes in bonds

 What do the arrows mean?

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Preparation of Nitriles

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Preparation of Nitriles from Amides

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Chapter 29
Analytical Chemistry
Chromatography
 Paper chromatography
 Two-way chromatography
 Thin-layer chromatography
 High-performance liquid chromatography
 Gas-liquid chromatography

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History of Chromatography
 Invented by Mikhail Tsvet
 Russian scientist
 Early20th century (1900’s)
 Coloured plant pigments

 Today most chromatography is carried out on

colourless compounds

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Paper chromatography
 Think back to IG

 Mobile phase
 Stationary phase
 R value
f

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Two-way chromatography

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Thin-layer chromatography
 Technique is similar to paper chromatography

 Theory is different

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 TLC relies on the fact that the attractive forces that
cause different compounds to be adsorbed onto a
solid surface differ from one compound to another

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High-performance liquid
chromatography

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Output High Performance Liquid
Chromatography

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Gas chromatography

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 In order to compare

 Flow rate
 Temperature
 Length and diameter of column
 Chemical make up of the solvent
 Polarity of the stationary phase

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 Retention time

 Measurement of the time it takes a substance to

reach the defector / travel through the stationary
phase

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Which peaks are good?

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Proton (1H) nuclear magnetic
resonance
 NMR
 Nuclear magnetic resonance
 Each H atom behaves like a tiny magnet

 Line up with or spin against magnetic field

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 Tetramethylsilane
 TMS
 Si(CH )
3 4
 Inert
 Volatile
liquid
 Mixes well with most organic compounds
 Only one peak

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Chemical shift δ
 Measured in ppm (parts per million)
 Shift away form the TMS line

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Low-resolution NMR
 Single peak for each non-equivalent hydrogen
atom

 Zero point on the x-axis is on the right

 Area under the peak tells use the relative number

of equivalent H atoms
 Shown with labels 1H, 2H, 3H

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High resolution NMR
 Peaks that appear as a single peak on low
resolution are often a group of close peaks
 Splitting pattern
 Caused by interference is called spin–spin coupling
 Depends on the number of hydrogen atoms on the
adjacent carbon atom or atoms
n + 1 rule

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 Equivalent protons don’t split

 Splittingis most commonly observed when

protons are separated by either two or three σ
bonds;

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16.17 Below are NMR spectra of several compounds.
Identify whether these compounds are likely to contain
ethyl, isopropyl, and/or tert-butyl groups:

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-OH and –NH- signal
 Field strength at which they resonate depends on
the acidity and hydrogen-bonding ability
 Easy proton exchange with other O—H or N—H
protons in the sample,
 These protons often do not cause the splitting of
the peaks of adjacent proton of the solution

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Deuterium exchange
 Heavy water D2O (D = 2H)
 Peaks due to the —OH or —NH2 protons
disappear
 Deuterium atoms do not absorb in the same region
of the electromagnetic spectrum as protons

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Analyzing a 1H NMR Spectrum
1. Always begin by inspecting the molecular
formula
2. Consider the number of signals and integration of
each signal
3. Analyze each signal
4. Assemble the fragments into a molecular
structure

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Carbon-13 NMR spectroscopy
 Simpler than a 1H spectrum
 Absorbances in a 13C spectrum usually appear as
singlets
 Very small natural abundance of 13C atoms
(1.1%), the chances of two adjacent carbon atoms
in a molecule both being 13C atoms is only just
over 1 in 100, and so the splitting of a peak due to
adjacent 13C atoms is very unlikely

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 Solvent CDCl3
 Small peak at 80ppm

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Predicting the number of signals and approximate
location of each signal
in a 13C NMR spectrum

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Putting it together

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DEPT 13C NMR Spectroscopy
a broadband-decoupled 13C spectrum does not
provide information regarding the number of
protons attached to each carbon atom in a
compound
 DEPT 13C NMR spectroscopy utilizes two rf
transmitters and relies on the fact that the intensity
of each particular signal will respond to different
pulse sequences in a predictable fashion,
depending on the number of protons attached
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Mass spectrometry
 Mass spectrometry
 study of the interaction between matter and an
energy source other than electromagnetic radiation.
 Usedprimarily to determine the molecular weight
and molecular formula of a compound.

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 Compound is first vaporized and converted into ions
 Which are then separated and detected. The most
common ionization technique involves bombarding
the compound with high-energy electrons.
 These electrons carry an extraordinary amount of
energy, usually around 1600 kcal/mol, or 70 electron
volts (eV).
 When a high-energy electron strikes the molecule, it
causes one of the electrons in the molecule to be
ejected.
 This technique, called electron impact ionization
(EI), generates a high-energy intermediate that is
both a radical and a cation.
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 This radical cation, symbolized by (M)+•, is called
the molecular ion, or the parent ion.
 The molecular ion is often very unstable and is
susceptible to fragmentation, which generates
two distinct fragments.

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 Cations are separated by their mass-to-charge
ratio (m/z). The charge (z) on most ions is +1, and
therefore, m/z is effectively a measure of the mass
(m) of each cation
 plot is then generated
 mass spectrum
 tallest
peak in the spectrum is assigned a relative
value of 100%
 Base peak

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 peak m/z = 17. This peak, called the (M+1)+• peak

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Analyzing the (M)+• Peak
 Some compounds, the (M)+• is the base peak
 Most compounds will easily fragment, and the
(M)+• peak will not be the most abundant ion
 In some cases, it is possible for the (M)+• peak to
be entirely absent, if it is particularly susceptible
to fragmentation

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 When analyzing a mass spectrum, the first step is
to look for the (M)+• peak, because it indicates the
molecular weight of the molecule
 Can be used to distinguish compounds

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 Useful information can also be obtained by
analyzing whether the molecular weight of the
parent ion is odd or even
 Odd molecular weight generally indicates an odd
number of nitrogen atoms in the compound
 Even molecular weight indicates either the
absence of nitrogen or an even number of nitrogen
atoms
 nitrogen rule

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High-resolution mass spectra
 can distinguish between ions that appear to have
the same mass on a low resolution mass spectrum
 molecular ion peak at 45 could be caused by
C2H7N or CH3NO
C H7N+ peak at 45.057 846
2

 CH NO+ peak at 45.021 462

3

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Using the [M + 1] peak
 Two stable isotopes of carbon, 12C and 13C
 Relative abundances are 98.9% for 12C and 1.1%
for 13C

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How many carbons in each

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M+2 and M+4 peaks
 Cl
 Br

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15.24 Below are mass spectra for four different compounds. Identify
whether each of these compounds contains a bromine atom, a chlorine

atom, or neither .

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Simple fragmentation

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Applications of the mass spectrometer
 Canbe link to gas-liquid chromatography
 Compared to known compounds

 Inresearch used to confirm structure of

undiscovered molecules

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Chapter 30
Organic Synthesis
Designing new medicinal drugs
 Predictthe shape
 Functional groups
 Molecule modelling

 Identifying macromolecules

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Chirality in pharmaceutical synthesis
 Enantiomers
 Optically active

 Racemic mixtures

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Prue enantiomers
 Lowerdosage
 Minimizes rick of side effects

 Opticalresolution
 Using optically active starting points
 Using a chiral catalyst

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Synthetic routes
 Work backwards
 Starting with commonly available raw materials

 Adding C atoms

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Goals
 Predicting the reactions of complex molecules you
have never seen before, containing more than one
functional group
 Suggesting a series of reaction to make a given
compound from a given staring point

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Review all
organic
chemistry
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R = hydrogen or methyl or other alkyl unless stated otherwise
R = hydrogen or methyl or other alkyl unless
stated otherwise

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R = hydrogen or methyl or other alkyl unless
stated otherwise
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R = hydrogen
or methyl or
other alkyl
unless stated
otherwise

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R = hydrogen or methyl or other alkyl unless stated otherwise
R = hydrogen or methyl or other alkyl unless
stated otherwise
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R =
hydrogen or
methyl or
other alkyl
unless
stated
otherwise

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 Aldehydes
 Ketones
 Carboxylic acids
 Phenols
 Esters
 Acyl chlorides
 Amides
 Amines
 Triiodomethane

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Chapter P2
Practical Skills two
Written examination of practical skills
 Paper 5
 Not in the LAB
 Two question 30 points

 Planning
 Analysis, conclusions, and evaluations

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Test percentage to A-level
40 points grade
30 points
12% 16%

23%
39%
60 points
100 points 12%

40 points

Paper 1 Paper 2 Paper 3 Paper 4 Paper 5

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Planning
 Two parts

 Defining the problem

 Methods

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Defining the problem
 Make a hypothesis/prediction

 Identify independent and dependent variables

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Methods
 How to do experiment
 Can’t ask you for help if directions are unclear

 Need to understand basic techniques and why used

 Draw apparatus and understand how to use data in

relevant calculations

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 How to lay out data

 Safety precautions
 Fume hood
 Gloves

 Accuracy of data

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Analysis
~Dealing with Data
 Read table of data
 Use data to find patterns and anomalous
 Averages
 Graphs
 Scales for axis
 To include (0,0)

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Evaluations
 Identify anomalous

 Quality of results and apparatus

 Appropriate
 Accurate

 Percent error

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Conclusions
 Compare to hypothesis

 Graph

 Improvements

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