3.

5 Organic Chemistry
5 Credits
Externally Assessed

Revision and Practice:

Naming
P79 in workbook
Need to still now the functional
groups from last year and their
reactivity
Five new functional groups in Yr13
These were introduced in 3.2
Spectroscopy
Now we learn how to name them and
Practice naming
and reactivity
about
theirP81-83
reactivity
on P85

Isomerisation
Functional

Structural

Positional

Chain

Isomer
s

C=C double bond

Geometric
Stereoisom
ers

NEW in Yr13

Optical
Isomerism P91 Part A, B and C

2 different
groups on each
carbon of C=C
Four different
atoms or groups
bound to a
central carbon
atom 3

Optical Isomers
Four different atoms or groups bound to a
central carbon atom
The central carbon is often called a chiral
or asymmetric carbon
Groups can be arranged 2 different ways
that are non-superimposable mirror
images of each other.
The two isomers are called enantiomers
E.g. butan-2-ol

Optical isomerism Part D: p 95, 96

Properties of Optical
Isomers
Identical physical and chemical properties
E.g. melting point, chemical reactivity

Can have different biological properties

since enzymes are also chiral compounds.
http://en.wikipedia.org/wiki/Thalidomide

Can be distinguished from each other by

how they rotate the plane of polarised
light.
Rotate by same angle but in opposite directions
Rotate to right: dextrorotatory d-enantiomer
Rotate to left: laevorotarory l-enantiomer
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Alkanes
General formula: CnH2n+2
Properties
Mp and Bp increase with chain size (more
intermolecular forces)
Non-polar: soluble in non-polar solvents but
not in water
Non-conducting

Reactions
Combustion
Substitution slow reaction with Br2 in the
presence of UV light
6

Alkenes
General formula: CnH2n
Geometric isomers
cis and trans

120 O

Properties
Similar to that of alkanes

Reactions
Combustion
Addition
Oxidation
Polymerisation

trigonal planar

Alkanes and Alkenes

Alcohols
General formula: CnH2n+1OH
OH = hydroxyl group
Classified as: primary, secondary and tertiary
Determined by the number of alkyl groups attached to the C
to which the OH is bonded.

Properties
Strong hydrogen bonds (H-bonds) between the polar hydroxyl
groups of neighbouring alcohol molecule
Higher Mp and Bp for equivalent alkanes (1 st 8 are liquids at RT)

Solubility:
Small chain alcohols are soluble in water can form H-bonds with
water
As alkyl chain length increases the non-polar properties limit
solubility in water. Alcohols with more than 6 C are insoluble in water
Alcohols are also soluble in non-polar solvents due to the non-polar
alkyl groups

Non-conducting

Classifying Alcohols P110

Alcohols
Reactions
Combustion
Oxidation
1 alcohols oxidise to aldehydes and then to
carboxylic acids
2 alcohols oxidise to ketones
3 cannot be oxidised

Chlorination (substitution)
Elimination (dehydration)
Alcohol Oxidation Investigation P112
116,
Alcocises P118 121 Q1,2,3, 7, 8, 9

Haloalkanes
General formula: CnH2n+1X
Classified as primary, secondary and tertiary
Relates to the number of C bound to CX

Properties
CX bond only slight polar so similar properties
to alkanes

Reactions
Nucleophilic substitution (OH -(aq), NH3(alc))
Elimination (heat/OH-(alc))
Unsymmetrical haloalkanes follow poor get poorer
Haloalkanes P125

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Amines
Classification
Primary: N has only one alkyl group, R-NH2
Secondary: N has two alkyl groups, R-NHR
Tertiary: N has three alkyl groups, R-NRR

Naming
Suffix amine
Longest alkyl chain gives base name
other alkyl groups attached to N are used
as prefix: N-alkyl.
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Amines
Properties
Bases
Turn damp red litmus blue

Strong H-bond between molecules gives high Mp

and Bp relative to alkanes
Low molar mass amines are soluble in water due
to H-bonding

Reactions
React with haloalkanes
Reaction water
Neutralisation of acids
Amines P131

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Aldehydes and Ketones

General formula: CnH2nO

C=O - carbonyl group
Aldehydes = alkanals suffix al
Ketones = alkanones suffix one
Properties
Polar C=O bonds give relatively strong intermolecular
forces
Higher Mp and Bp for equivalent alkanes but lower than alcohols
Increase with increasing molar mass

Solubility:
Small chain aldehydes and ketones are soluble in water can
form H-bonds with water
aldehydes and ketones are also soluble in non-polar solvents
due to the non-polar alkyl groups

Non-conducting

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Reactions of aldehydes and ketones

Preparation
Aldehydes: oxidation of 1 alcohols
Ketones: oxidation of 2 alcohols

Reduction
Sodium borohydride (NaBH4) provides an
H- to reduce the carbonyl
Aldehydes are reduced to 1 alcohols
Ketones are reduced to 2 alcohols
Aldehydes/ketones

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Distinguishing between aldehydes

and ketones
Aldehydes can be distinguished from
ketones because they can be easily
oxidised to carboxylic acids whilst
ketones do not react
Oxidant
Colour change
potassium dichromate
(acidified)
potassium permanganate
(acidified)

Orange solution to green Oxidise

alcohols +
aldehydes
Purple solution to colourless

Tollens reagent Oxidise only Colourless solution forms silver

aldehydes precipitate or silver mirror
Benedicts solution

Blue solution forms orange-red

precipitate

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Carboxylic acids

General formula: CnH2nO2

-COOH suffix anoic acid
Carboxylic acids are weak acids
Properties
Strong hydrogen bonds (H-bonds) between the
carboxylic acid groups of neighbouring molecules
form dimers
Have much higher Mp and Bp than equivalent alkanes and
alcohols

Solubility:
Small alkyl chain carboxylic acids are soluble in water
can form H-bonds with water
Water-insoluble carboxylic acids are more soluble in a
NaOH solution, due to the formation of a carboxylate ion

Weakly conducting in aqueous solution

16

Carboxylic acids
Reactions
Preparation oxidation of primary
alcohols with a reflux condenser
Neutralisation
React with metal carbonates, metal
oxides and reactive metals to form ionic
salts suffix anoate

P147 Q1, P149 Q1-8, 10,

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Esters
R-COO-R where R and R are alkyl
chains
Naming:
Esters are made from carboxylic acids (or
acid chlorides) and alcohols. Both parts
contribute to the name
alcohol part comes first
acid part comes second
Dont forget to include the C in the COO when
naming the acid part

Name is written as two words because

there are two parent chains present

18

Esters
Properties
Esters are:
Colourless liquids
More volatile (lower Bp) due to no Hbonds
Not very soluble in water
Have characteristics smells often used
in perfumes.

Naming esters P154 Q1

19

Esters
Preparation
esterification reaction
acid chloride and alcohol
carboxylic acid, alcohol and conc. H2SO4 catalyst
(condensation reaction)

Hydrolysis of esters
Reverse of esterification
acidic conditions
basic conditions

Amide formation
Esters react slowly with NH 3
Ester reactions: P155 Q 2, 3, 5, 6, P 167

20

Acid Chlorides
General formula: CnH2n-1OCl
Derived from -COOH by substituting the OH
with a Cl.
Naming:
change the e of the alkane to oyl chloride
numbering starts from the COCl group

Properties
Low Mp and Bp since there is no H-bonding
between molecules
Pungent, fuming liquids
Naming p169 Q1

21

Acid Chlorides
Formation
Substitution using thionyl chloride, SOCl2
(or PCl5, PCl3)

Reactions
Highly reactive as C is attached to two
highly electronegative atoms giving it a
strong + charge
+ C is readily attacked by nucleophiles
such as NH3, H2O, aminoalkanes and
alcohols in nucleophilic substitution
22

Acid Chloride reactions: P169 Q 2, 3, 4, P172 Q 7 and reaction scheme

Amides
General formula: RCONHR
Amide: -CON Naming:
With primary amides (R = H) suffix = anamide
With amides with alkyl group on nitrogen use:
Prefix: N-alkyl for the alkyl group on the N, E.g. Nmethyl
Then length of C chain, e.g. ethan
Suffix: amide
E.g. CH3CONHCH3

Naming p173 Q1

23

Amides
Properties
White crystalline solids (except
methanamide)
High Mp and Bp due to strong H-bonding
Lower molar mass amides are soluble in
water
Not basic (unlike amines)

Reactions
Preparation of primary amides
Carboxylic acid + ammonia
Ester + ammonia
Acid chloride + ammonia

24

Amides
Preparation of N-substituted amides
Acid chloride + amine

Hydrolysis of amides
Acidic conditions
Basic conditions

Reactions P174 Q2, 4

25

Amino Acids
Contain both NH2 and COOH
Building blocks of peptides and
proteins
20 used in proteins
Differ in their side chains off the second
carbon

26

27

Amino Acids
Contain both NH2 and COOH
Building blocks of peptides and proteins
20 used in proteins
Differ in their side chains off the second carbon

All natural amino acids, except glycine

(aminoethanoic acid), form optical isomers
Amino acids tend to exist as ions
(zwitterion) and are therefore very soluble
in water
28

Condensation Polymers
Polymerisation involving the elimination of a
simple molecule (such as water) as monomers
join together
Include:
Polyesters
Polyamides
Proteins

Can involve one monomer with a COOH and a

OH or NH2 or two monomers
a dicarboxylic acid or a diacid chloride and diol
a dicarboxylic acid or a diacid chloride and diamine
29

Peptides
When two amino acids (AA) are joined together
a peptide (amide) bond is formed, making a
dipeptide
When many AA join together a polypeptide is
made
A polypeptide with a known function is called a
protein e.g. insulin, collagen, enzymes
Hydrolysis of peptides and proteins produces
the various AA from which it was made
Acidic and basic conditions will produce AA in
different forms
P178 and 179

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