Organic Chemistry : Contents

1. Introduction
Some basic knowledge to get in Organic Chemistry.
- Introduction Part 1
- Introduction Part 2


2. Alkane
The easiest molecule to start.
 
3. Alkene 
Just like Alkane, only some double bonds.


4. Aromatic 
When carbon gets into cycle.
- Examples of Miscellaneous Reactions of Aromatic Compounds 1
- Examples of Miscellaneous Reactions of Aromatic Compounds 2


5. Carbonyl Group
Oxygen has a double bond with Carbon. 
- Aldehyde and Ketone 1
- Aldehyde and Ketone 2


6. Carboxylix Acid
The well-known organic acid.


7. Carboxylic Acid Derivatives
Some functional groups similar to carboxylic acid.  
- Ester and Amide 1
- Ester and Amide 2


8. Amine
Let's try out Nitrogen.

Organic Chemistry : Amine

Amine is a Nitrogen functional group. (Excluding Amide, which we have known as a more specific functional group.) It can be -NH₂ or, possibly, H in -NH2 can also be replaced with other groups such as -NHCH₂CH₃.

Primary amine	Secondary amine	Tertiary amine

  IUPAC Names
- Find the longest carbon chain containing the amine group.
- The position of any group attached to Nitrogen atom is denoted as N. (We need to ignore alphabet arrangement for N position because N position must be arranged at the first if exists.)
- Then, the name is formed by changing the -e of the alkane one to -amine.
- The position of Nitrogen attached to Carbon is indicated by number before -amine.
- Example :  CH₃CH₂CH(NHCH₂CH₃)CH(CH₂CH₃)CH₂CH₂CH₃ = N,4-diethyl-3-heptanamine.
Fun Facts :  a well-known illegal drug, amphetamine, is actually 1-phenyl-2-propanamine.

 Physical Properties


Boiling Point
With N-C bonding, it has higher boiling point than other unpolar organic substances, but still lower than other O-C-bonding polar ones such as Carboxylic acid or Alcoho.

Solubility
With its polar, it is soluble with water, except only aromatic amine. As usual, the bigger of molecule, the lower solubility.

Base of Amine
 Since Nitrogen has 5 electrons and 3 of them are used for 3 single bonds, there are 2 of them left. Those 2 can be used to donate to Hydrogen ion (Proton.) Thus, Amine is base.


Reaction

1. Amide can be yield by reduction of Nitro.

2. Reaction with Nitrous acid.

- Primary

 

Example :

- Secondary

Example : 

- Tertiary

You will get nothing! (Just a weak base reacting with weak acid.)

 Reference : BCC M.5 Chemistry Book.
http://en.wikipedia.org/wiki/Amine
http://www2.chemistry.msu.edu
http://www.chemguide.co.uk
http://www.pharmgkb.org

Organic Chemistry : Ester and Amide 2

Ester Reaction

1.  Ester can be yield as below. Do it backward called Hydrolysis

 

 2. Saponification

 

 3. Transesterification

 4. Reduction

 Amide Reaction

1. Hydrolysis

2. Reduction

3. Hoffmann Rearrangement

 Reference : BCC M.5 Chemistry Book.
http://en.wikipedia.org/wiki/Ester
http://en.wikipedia.org/wiki/Amide
http://image.wistatutor.com

Organic Chemistry : Ester and Amide 1

From previous group, -COOH, sometimes we have some slightly different organic substance, just replace H in -COOH into others. For example, -COOCH₃ , -COONH₂. These are called Carboxylic Acid Derivatives. Here, we will study only two big ones, Ester and Amide.
- Ester : Replace H in -COOH with some other group such as -COOCH₂CH₃.
- Amide : Replace H in -COOH with N such as -COONHCH₂CH₃.

IUPAC Names

Ester
- Find the longest carbon chain containing the ester group, where the position of the carbonyl carbon must be the first.
- Call the secondary group that replaces the H in -COOH, then call the other side. (the carbon chain side)
- Then, the name is formed by changing the -e of the alkane one to -oate.
- Example :  CH₃CH₂CH₂CH₂-COOCH₂CH₃ = ethylpentanoate

Amide
- Find the longest carbon chain containing the amide group, where the position of the amide  carbon must be the first.
- Call the secondary group (-NRR') that replaces the H in -COOH, then call the other side. (the carbon chain side)
- The position of the Nitrogen atom is denoted as N. (We need to ignore alphabet arrangement for N position because N position must be arranged at the first if exists.)
- Then, the name is formed by changing the -e of the alkane one to -oate.
- Example :  CH₃CH₃CH₂CH(CH₂CH₃)CH₂-COONHCH(CH₃)₂ = N-1-methylethyl-3-ethylhexanamide


Physical Properties

Boiling Points
Amide is the organic substance with the highest boiling point because of dimers (same as carboxylic acid, but stronger.) Ester's boiling point is really low, since the polar around carbonyl group is pretty weak compared to Aldehyde, Ketone, or Carboxylic acid.

Solubility

Carboxylic Acid Derivatives are mostly the same as old carboxylic acids. So small carboxylic acids derivatives are usually soluble.





 Reference : BCC M.5 Chemistry Book.
http://en.wikipedia.org/wiki/Ester
http://en.wikipedia.org/wiki/Amide
http://image.wistatutor.com

Organic Chemistry : Carboxylix Acid

Carboxylic acids are organic substance with carboxyl group; R-COOH, where R is some monovalent functional group. (lower priority groups.) A carboxyl group (or carboxy) is a functional group consisting of a carbonyl (RR'C=O) and a hydroxyl (R-O-H) so it has the formula -C(=O)OH, which is usually written as -COOH.

 

IUPAC Names

- Find the longest carbon chain containing the carboxy group.
- Then, the name is formed by changing the -e of the alkane one to -oic acid. 
- The position of the carboxy group is always the first.
- Example :  CH(CH₃)₂COOH = 2-methylpropanoic acid.

Physical properties

Solubility

Carboxylic acids are polar because there are both hydrogen-bond acceptors (the carbonyl) and hydrogen-bond donors (the hydroxyl). So they can do hydrogen bonding to water.  However, only small carboxylic acids (1 to 5 carbons) are soluble.

Boiling points

Carboxylic acids have highboiling points because of their two hydrogen bonds per pair of molecules (called dimers.) 

Acidity

Carboxylic acids are weak acids. Here are some examples :

Carboxylic Acids	pKa
Formic acid (HCO2H)	3.77
Acetic acid (CH3COOH)	4.76
Chloroacetic acid (CH2ClCO2H)	2.86
Dichloroacetic acid (CHCl2CO2H)	1.29
Trichloroacetic acid (CCl3CO2H)	0.65
Trifluoroacetic acid (CF3CO2H)	0.5
Oxalic acid (HO2CCO2H)	1.27
Benzoic acid (C6H5CO2H)	4.2

 

Reactions

We can do reduction.

 

And we can also use Carboxylic acid to have other organic function groups. 

 Reference : BCC M.5 Chemistry Book.

http://en.wikipedia.org/wiki/Carboxylic_acid 

http://tutorvista.com

http://www.bmrb.wisc.edu

 

Organic Chemistry : Aldehyde and Ketone 2

Now, let's move on to the reactions they can have.

1. Oxidation
Can be used to know whether substance is Aldehyde or Ketone. Note that Aldehyde is always easier to do reactions.
- Tollen's Reagent >> give Ag as positive test, this is why it can be called Silvor Mirror Test
- Benedict' Reagent >> give Cu2O, a yellow, orange, or red dregs.
- Fehling's Reagent >> same as Benedict's

2. Reduction

3. Clemensen Reduction

 

 Reference : BCC M.5 Chemistry Book.

http://en.wikipedia.org/wiki/Aldehyde

http://en.wikipedia.org/wiki/Ketone 

Organic Chemistry : Aldehyde and Ketone 1

We have studied organic substances that consist of only Carbons and Hydrogens. (All we have studied is the difference when the bondings and structures are different.) From now, we are going to add a new one; Oxygen.

In this, we will consider Oxygen that has a double bond to Carbon only (called Carbonyl group), which can be classified as Ketone or Aldehyde , depending on the Carbon Oxygen is bonding to as below:

Note that "R" stands for any alkyl.

IUPAC Names 

Aldehydes
- Find the longest carbon chain containing the aldehyde group. Carbon with aldehyde group is always numbered as first one.
- Then, the name is formed by changing the -e of the alkane one to -al. 
- Examples : HCHO = methanal, CH₃CH₂CH₂CHO = butanal.

Ketones
- Find the longest carbon chain containing the kerone group.
- Then, the name is formed by changing the -e of the alkane one to -one. 
- The position of the carbonyl group is denoted by a number.
- Example :  CH₃-CO-CH₃ = 2-propanone.

 Physical Properties
The carbonyl group is polar as the EN of the oxygen is greater than carbon. So, oxygen has negeative polar while carbon has positive so that Aldehydes and Ketones can do hydrogen bonding with water. They are more soluble in water if they are not too big - more than 4 carbons. However, polar in Aldehydes and Ketones gives them somewhat higher boiling and melting points. (But still lower than some like alcohol or carboxylic acid.)

 Reference : BCC M.5 Chemistry Book.

http://en.wikipedia.org/wiki/Aldehyde

http://en.wikipedia.org/wiki/Ketone 
http://www.chm.bris.ac.uk 
http://www.elmhurst.edu

Examples of Miscellaneous Reactions of Aromatic Compounds 2

2. Reaction of : Toluene + Nitric Acid

Let's make a bomb!!

First, nice to meet you, Toluene.

Toluene (or toluol) is Benzene that has been replaced its Hydrogen with methyl (CH₃.) For the process, we can do Friedel–Crafts reaction (but no details will be explained here.) Toluene's pictures :

In the reaction to create the bomb, we need to replace another three nonneighboring Toluene's Hydrogen with NO₂. In the first time, we use H₂SO4 and HNO₃ (Nitric Acid) to have mono-nitrotoluene or MNT from Toluene. Do Nitration again to MNT then we will get  dinitrotoluene or DNT. Last, use dehydrate mixture of HNO₃ and H₂S₂O7 with DNT and we will get trinitrotoluene or TNT.

Conclusion : replace Hydrogen with NO₂ 3 times.

And well, trinitrotoluene or TNT (C₆H₂(NO₂)₃CH₃ as shown at the right side) is exactly the one we commonly hear as a bomb.


Refrerences :
http://en.wikipedia.org/wiki/Toluene
http://en.wikipedia.org/wiki/Trinitrotoluene
http://en.wikipedia.org/wiki/Mononitrotoluene

Examples of Miscellaneous Reactions of Aromatic Compounds 1

1. Polymerization of Styrene

We can have Polysterene (a kind of foam) by using continuously many Sterenes. Sterene, or  Vinyl Benzene, is Benzene that has been replaced one of its Hydrogen with C2H2. So its formula is C₆H₅CH=CH₂ as shown below.

Now, when we let Sterenes do a reaction at their C2H2 (because around their hexagon, they are aromatics, which are hard to do any reactions.) by destroying a pi bond in each of Sterenes in the free radical way so that unbonded electrons after the free radical will be used to be a sigma bond with other similar Sterenes.

Bit of knowledge >>> Polysterene we get do not always need to have the aromatic groups (the hexagons you see) at the same side. For example: below are some of unneccessary ones.

References :
 http://en.wikipedia.org/wiki/Styrene
 http://en.wikipedia.org/wiki/Polystyrene
 http://www.pslc.ws/mactest/styrene.htm