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ORGANIC CHEMISTRY 1.2- AMINES

i) STRUCTURES OF AMINES
Amines are derivatives of ammonia in which one or more hydrogen have been replaced by alkyl group or aryl group.

General formula:
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
If two hydrogens have been replaced we have;
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
2° amine
If 3 hydrogens have been replaced we have;
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
3° amine
NOTE:
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

Quatenary salt of amine
ii) (NOMENCLATURE) IUPAC SYSTEM
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES 4 – aminobutanoic acid


iii ) PREPARATION OF AMINES
1.ALKYLATION OF AMMONIA WITH HALOALKANES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
1EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES amine can be obtained by reaction of alkyl halide with excess ammonia.
Why excess ammonia?
So as to prevent the formation of 20 amine or 30 amine. Therefore, this is not a suitable for preparation of amine because the substitution of hydrogen does not stop at the first stage.

EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
2. REDUCTION OF NITROALKANES (R – NO2)
10 amines can be obtained by reduction of nitroalkane. The reducing agent is LiAlH4 or Sn/HCl or Fe/HCl
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
3. REACTION OF AMIDES WITH LiALH4
1EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES amides can be reduced to 10 amines
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
4.AMMONIATION OF CARBONYL COMPOUND FOLLOWED BY REDUCTION WITH HYDROGEN IN THE PRESENCE OF NICKEL
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

5. REDUCTION OF NITRILES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
6. REACTION OF ALCOHOLS WITH AMMONIA
Catalytic ammoniation of alcohol gives a mixture of amines.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
7. HOFFMAN’S DEGRADATION OF AMIDES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
It is important reaction in the conversion of amide to amine with one carbon less.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
(i) By Hoffman’s degradation reaction
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Solution:
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
4.PROPERTIES OF AMINES
a)PHYSICAL PROPERTIES OF AMINES
Boiling point and melting point
Amines have high boiling and melting points due to their ability to form hydrogen bonding as compared to hydrocarbons.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
(i) Its boiling point is lower than alcohol (R – OH)
Reason: In oxygen, there are 2 lone pairs which increase its chance of hydrogen bonding.
It also has lower boiling point than carboxylic acid.
10 amines have high boiling point than 20 amines. For 30 amines, there is no possibility of H –bonding since Nitrogen is not attached to hydrogen.
(ii) Solubility:
Lower aliphatic amines are soluble in water.
Reason:- They can form hydrogen bond with water.
As the molecular mass increases, solubility decreases.
Reason: -The long chain of hydrocarbon (R) is insoluble since it is water phobic. As the alkyl group becomes bigger, solubility decreases.
Amines containing 6 or more carbon do not dissolve in water.
E.g: aniline is insoluble due to this reason.
b)CHEMICAL PROPERTIES OF AMINES
1. Basic character
Amines are the most important organic bases. Aliphatic amines are slightly stronger Lewis bases than ammonia. Lone pair an the nitrogen is readily available to accept proton in amines than it is an ammonia .

R R— Positive inductive effect
| |
R-NH2 R-N-H R-N-R
20 amine the strongest base among the three
The stability of hydrated ion decrease from 10 amine 30 amine
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Reason:- 30 amines forms a very unstable ammonia salt. Although it can easily donate a lone pair of electrons as compared to 10 and 20 amines, it forms very unstable hydrated ion.
Note:
The inductive effect on alkyl group tends to make 30 amines more basic while hydration effect tends to make 1EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES amine more basic. As a result of the combined effect of these two the observed order of the base strength will be;
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Methylammonium chloride
Q. Between the following amines, which is stronger base
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Reason:- In Aniline there is negative mesomeric effect since lone pair is withdrawn from the amine group.
Mesomerism of aniline
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
For aromatic compounds, the lone pair is less readily available for protonation (addition of proton)
EFFECT OF SUBSTITUENT GROUP ON THE BASICITY OF ANILINE
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
· All activators make aniline more basic while deactivators make aniline less basic.
Electrons supplying groups
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Electrons withdrawing groups
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
2. Alkylation (reaction with haloalkanes)
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINESEcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Example:
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Quatenary salt
3. Reaction with ketones and aldehydes
Both aliphatic and aromatic 10 amines react with aldehydes and ketones to form a base known as Schiff’s bases.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINESSchiff’s base
E.g:
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
-Lewis acid is a substance that accepts a lone pair of electrons
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
4. Reaction of 10 amines with chloroform (carbylamines reaction)
· Both aliphatic and aromatic amines on heating with chloroform and alcoholic KOH given isocyanides (carbylamines)
· The isocyanide form has offense smell. It is used to identification test for 10 amine
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Carbylamines (offense smell)
This reaction is a Test for 1EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINESamine
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
(i) Convert;
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
5 . Acylation
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
N – methylethanamide
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
N – phenylethanamide
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
6. Reaction with Nitrous acid EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

Note: It is used as a distinguishing test between different classes of amines.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES Amine
· Aliphatic EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES amine reacts with HONO to form alcohol and nitrogen gas (you will see bubbles)
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
E.g:
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
– For aromatic amine react with HNO2 in cold (below 5ºC) to form diazonium salt.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES Amine
· EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES amines react with nitrous acid to give N – nitrosoamine which separate out as a yellow oily liquid.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES




N- nitrosoamine

(Yellow oil liquid)
It is a distinguishing test since we see yellow oil liquid
Eg:
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES Amine
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES Amine reacts with nitrous acid to form a soluble trialkylammonium salt which is colourless.
It is not a distinguishing test since there is no observable change.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Aromatic 3EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES amines react with HONO to give green colour p – nitrosoamine
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
This is a distinguishing Test since there is a green colored
Reaction of amines with metal ions Ag+ & Cu2+
Reaction of aromatic amine due to benzene ring
1. reaction with bromine water
· Aniline undergoes halogenations even in the absence of catalyst. With bromine it gives
2, 4, 6 – tribromoaniline (white solid)
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Here benzene ring is highly activated due to the presence of amine

To obtain mono substituted derivative, aniline should be first acylated then halogenation. After halogenations, the acyl group is removed by hydrolysis to obtain mono substituted aniline.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
2. Nitration
Direct Nitration is not possible because aniline gets oxidized. Amine group should be protected by acylation, then nitration and finally hydrolysis.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
3. Sulphonation
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

We have different products due to H – bonding. At 1800C, H – bonding will not be effective hence SO3H will be at para position.
4. Diazonium salt
· It is used to form many other products.
· Reaction is nucleophilic substitution EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

H/W
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
3. Why is phenylamine more soluble in EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES than in H2O?
4. Define the term “base.” Write down structural formula of the following compounds and arrange them in order of increasing basic strength;
Methylamine, ammonia, ethylamine, ethanamide, phenylamine. Give reasons.
5. Give structural formula of the organic products that are obtained when;
(a)Ethylamine
(b)Phenylamine
(c)Phenylmethylamin
(d)N – methylphenylamine are treated with;
(i) Chloromethane
(ii) A mixture of NaNO2 and HCl
(iii) Benzoylchloride
ANSWERS
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Phenylamine is more soluble in HCl since they will form a stable hydrated ion but it is less soluble in water due to the large hydrophobic part i.e. the benzene ring.
4. A base is a substance which releases OH as the only negative ion.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
QUESTIONS
1.An aromatic compound contains 80% carbon, 9.6% hydrogen and nitrogen. Its relative molecular mass is 135g/mol. It is slightly basic and form salts but given no other reaction nitric (III) acid. Identify the structure of this compound.
2. An organic base A contains 61% carbon, 15.3% hydrogen, 23.7% nitrogen. When treated with nitric (III) acid A yield an alcohol B and nitrogen gas is evolved. The alcohol B contains 60% carbon, 13.33% hydrogen and on careful oxidation yields compound C, which has a vapour density of 29. Compound C forms an oxime with hydroxylamine (H2 N – OH) but does not react with Fehling’s solution. Suggest structures for the compounds A, B and C and indicate the cause of the above reactions.
3. How does the introduction of nitro group – 2 – and – 4 – positions of phenylamine affect its basicity? Give reasons


(a) Give the conditions under which the following reactions proceed
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
(b) Write the structural formula for each of the organic compound formed when compound M reacts with each of the following;

EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

ANSWERS:
1.

C
H
N
Percentage
80
9.6
10.4
R.M.M
12
1
14
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINESby R.M.M
6.666
9.6
0.7428
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINESby smallest number
8.97
≈ 9
12.924
≈ 13
1
1

Structure of the compound is C9 H13 N
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Molecular formula: EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
Probable structural formula:
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
2.
C
H
N
Percentage
61
15.3
23.7
R.M.M :
12
1
14
Percentage divide by
R.M.M
5.083
15.3
1.69
divide by the
smallest no
3
9.05
1
Empirical formula C3 H9 N
The organic base will be EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
3. The nitro group attached to position – 4 – will make phenylamine to be more basic than the nitro group attached to position – 2
Reason:- This is because in – 2 – nitrophenylamine there might be hydrogen bonding between the hydrogen and oxygen hence basicity will decrease.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
QUESTIONS
Give the equations for preparation of propanoic acid stating with;
(a) Haloalkane
(b) Ethene
Give equations (including reagents and conditions) for the following conversions;

EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
3. Arrange the following compoounds in order of their increasing acidity. Explain the differences in their acidity.
a) ethanol
b) Ethanoic acid
c) Pentanoic acid
d) Ethanedioic acid
e) 1, 2 – benzenedicarboxylic acid
f) Trichloroethanoic acid
g) Butenedioic acid
4. Convert the ethanoic acid into;
a) Ethylethanoate
b) Ethanoylchoride
c) Ethanol

d)Trichloromethanoic acid
e) Ethanamide
For each each conversion give a chemical equation
5. A compound A of molecular formula C4H8O2 gives propane when fused with alkali. When A reacts with Na2CO3(aq), CO2 is evolved. When A reacts with molecular formula C8H14O4 which on strong heating yield 2, 4 – dimethylpentanone. Establish the structural formula of A & B and give reason.
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES
EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES


EcoleBooks | CHEMISTRY A LEVEL(FORM SIX) NOTES - ORGANIC CHEMISTRY 1.2- AMINES

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