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Title: F324 A2 chemistry
Description: These notes cover all aspects of the module F324, the only thing required is to fill in the boxes with diagrams and add curly arrows to the mechanisms.

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F324 notes
Arenes
Structure and bonding in benzene:






Each Carbon makes 3 -bonds: 1x C-h and 2x
c-c
All bond lengths between carbons are equal
P-orbitals on adjacent carbons overlap
sideways to form a π-system
π-system had 6 e- delocalised across all
carbons in the ring
π-system e- density above and below the ring
...
H2SO 4

+ H2O

≤ 10°

(Conc
...




[H] = reducing agent NaBH4 (2 per reduction)
Wet tests for carbonyl compounds:
1) H+/Cr2O72
Observation: orange to green
2) Tollen’s reagent
Conditions: Tollen’s + heat + ethanol (solvent)
Observation: Silver mirror
3) 2,4 – DNPH
Orange precipitate with pure carbonyls – aldehyde and ketone, re-crystallise and find MP of
crystals and compare to a data bank of crystals
...


Mechanism in words:
1) Hydride ion nucleophilically attacks the C to make a dative covalent bond
2) The C=O π-bond break heterolytically towards O to generate an oxyanion (O -)
3) 1 lone pair from O- forms a dative covalent bon to H from water
Esterification
Esters are used for perfumes/flavourings
...
C : No
...
If there is H directly next to N, O or
F within a molecule, H bonding will take
place between molecules
...

Amino acids:
α amino acids – amine and carboxylic acid attached to same
carbon
...


F324 notes
Above the isoelectric point: everything that can be protonated will be deprotonated
...


Below
+

At
0

Above
-

Formation of polypeptides:

Synthesis:

NH2
NH2
Aromatic amine

Aliphatic amine

Preparation of aliphatic amine:
Halogenoalkane + ammonia

Mechanism:

aliphatic amine

NH2
aliphatic amine

F324 notes
Condtions:



Excess of ammonia – minimises reaction with product
Ethanolic ammonia – prevents formation of an alcohol

Preparation of an aromatic amine:

NO2

NH2
+

6 [H]

+

Sn/Conc
...

Optical isomerism

Carbon attached to 4 different groups
causes chirality
...

1x chiral carbon = 2 versions
2x chiral carbon = 4 versions

Problems with chirality:
For the patient –



One isomer may have harmful side effects
One isomer may be biologically inactive; increased dose required (liver)

F324 notes
For the pharmaceutical company –



One isomer may be biologically inactive; increased dose required (money)
Chiral seperation is expenssive and difficult

Methods to prevent chirality:
During synthesis –



Use naturally occuring enzyme
Chiral pool synthesis

After synthesis –


Chiral seperation
Polyesters and polyamides

Polyesters:
Method 1:

Method 2:

Polyamides:
Method 1:

F324 notes
Method 2:

Hydrolysis of polymers:
Polyester:

Acid:

Alkali

Polyamide:

Acid:

Alkali

Analysis
Chromatography:
Seperates components in a mixture between a stationary phase and a mobile phase
...
Adsorbtion is the process where a solid holds gas or liquid on the surface of a solid
...

RF value: ratio of distance migrated by a substance compared with solvent front
...

Highy temperatures so unsuitable for biological molecules
...

Limitations of gas chromatogtaphy:



Similar substances have similar retnetion time
If unknown substance, no retention time recorded

GC may be combined with mass spectroscopy to make it more useful – can be used in forensic
investigations
...

13C

spectrum tells you:



Number of different carbon environments
Types of carbon environments

High resolution 1H spectrum tells you:





Number of proton environments
Type of proton environment
Relative number of protons in different environments
Number of adjacent protons

Sometimes you see a peak at 0, tetramethylsilane (TMC) is assinged this number and used to
calibrate the scale
...

All normal solvents have protons and would produce their own peaks deuterated solvents e
...
CDCl 3
is used – these do not produce a signal due to 2H
...
When added, N-H or O-H groups siganl disappears
as D replaces H; these protons are said to be labile
...

5 scenarios for signal splitting:
1
...
Protons on adjacent carbons on one side only simply follows n+1 rule
3
...
Protons on adjacent carbons on more than one side with unequal amount of protons forms
a mulitplet
...
OH and NH (SH) do not get involved in splitting
Title: F324 A2 chemistry
Description: These notes cover all aspects of the module F324, the only thing required is to fill in the boxes with diagrams and add curly arrows to the mechanisms.