Functional Groups in Organic Chemistry Page 1

Hydrocarbons Alkyl Halides

The two carbons with the double bond are sp2–hybridized, and the geometry is
If we draw any alkane and remove one of the hydrogens, this brings
These, as the name suggests, are compounds that consist of carbon and hydrogen trigonal planar with a 120o angle between the atoms. The double bond is made of R X
the possibility of placing other atoms or groups on the position. For
atoms. And depending on the connectivity and bonding types, we divide them into one and one bond. X = halogen
example: Cl
five main categories: I
Br
Alkynes
Alkanes, alkenes, alkynes, cycloalkanes and aromatic compounds.
The difference between alkynes and alkenes is the change
The hydrocarbon chain is often represented with letter R to keep the structure short.
Alkanes R R'
of the double bond to a triple bond. The ending changes
This R is what we call an alkyl group, which by itself is shown with a line on the
R Alkanes are the first group of organic compounds. They
R = H, Alkyl from -yne:
position where we removed the hydrogen:
R C R are made of carbons and hydrogens that are only
R connected with single ( ) bonds. Alkynes have two hydrogens less H3C CH2 CH3 CH2 CH2
R = H, Alkyl
You must know the first ten alkanes and their names: than the corresponding alkenes and
ethyl propyl phenyl
therefore the general formula is
Number of CnH2n-2
Formula Name
C atoms Nitriles
Alkyl groups together with the -CN (cyano) group make the nitriles:
Cycloalkanes Cycloalkanes have the same hybridization as the alkanes and R C N
CN CN
only single bonds are present in the molecule. One important CN
CH2 difference is the change of the general formula to CnH2n as
n
there are no terminal CH3 groups: Acetonitrile is a common solvent in organic laboratories and many other nitriles are

used in synthetic polymers and glues.

C3H6 C4H8 C5H10 C6H12
cyclopropane cyclobutane cyclopentane cyclohexane

Aromatic compounds Alcohols If instead of the halogen, we put an OH (hydroxyl group) on an

All aromatic compounds are cyclic and have a double bond on alkyl halide, we get an alcohol. For the general formula, we have
R OH
every second carbon. It goes interchangeably single-double. Here R-OH and below are some common examples: OH
Benzene are some comon aromatic compounds: OH
Key features: General formula - CnH2n+2 . For every n carbon, the molecule
H3C OH OH
has 2n+2 hydrogens. O O
CH3 OH NH2 C C Methanol Ethanol Isopropanol Phenol
All the carbons are sp3-hybridized, only single bonds, all the bonds are OH H

non-polar, therefore, alkanes and all the other hydrocarbons are non-polar, Toluene Methanol – important organic solvent, very toxic, causes blindness
Phenol Aniline Benzoic acid Benzaldehyde
hydrophobic molecules. Ethanol – the alcohol in beverages
O
O
SO3H C Isopropanol – this is the rubbing alcohol
CH3
Phenol – an important aromatic alcohol with many applications
Anisole Benzenesulfonic acid Acetophenone Styrene

Thiols
Alkenes All the carbon atoms in benzene are
The Structure of Benzene
The sulfur analog of alcohols is the thiol functional group:
Alkenes are similar to alkanes with the only difference C=C sp2 carbons
R SH
R R sp2 hybridized connected by sp2–sp2 bond trigonal planar geometry SH
being the presence of a double bond. The R groups can be
s
om

H H SH
at

single bonds and each has a p orbital H SH

he

R R H or hydrocarbon chains (see below about the alkyls). H

ft
eo

H H
an

This double bond changes the suffix from -ane to -ene. perpendicular to the plane of the atoms. p orbitals - 90o to the plane
pl

R = H, Alkyl
Thiols are reducing agents and play an important role in preventing

Notice that not every cyclic compound with a double bond(s) is oxidative damage in cells. One noticeable example is the glutathione which

aromatic – it must have a certain number of alternating p bonds. as antioxidant in plans and is used by humans as a supplement.
cyclohexene
For example, a ring with one double bond is a cycloalkene:
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 Functional Groups in Organic Chemistry Page 2
Ethers Ethers are different from alcohols in that the hydrogen of the Aldehydes Connecting a hydrogen with a carbonyl group gives an aldehyde:
hydroxyl group is replaced with another alkyl group. So, to O
R O R' O O O
recognize the ether in an organic molecule, look for the R H
H H H H3C H
bridging oxygen:
Formaldehyde Acetaldehyde Benzaldehyde
O O O

Dimethyl ether Diethyl ether Methyl propyl ether

The simplest aldehyde with one carbon atom is the formaldehyde followed by the

acetaldehyde.e synthesis of many chemicals.chemical industry. It is also produced Amides

The most commonly used ether is the diethyl ether which is an organic solvent in the human body from ethanol by the Alcohol dehydrogenase enzymes and is Amides are the combination of the carbonyl and amines:
O
and was previously used as a general anesthetic. partly responsible for the cause of the hangover. R
O
N R' O O
N
R'' H N N
Thioether (Sulfides) H

Since sulfur is often divalent (makes two bonds) it also serves as Ketones Putting alkyl groups on both sides of the carbonyl switches
Depending on the number of carbons connected to the nitrogen, we have primary,
R S R'
a bridge for two alkyl groups: from aldehydes to ketones:
O O secondary and tertiary amides. Notice that the carbonyl carbon is also counted:
R
S O O
R O O
S O
S
N N
Acetone Diethyl ketone Acetophenone NH2
H
These are called thioethers or sulfides.
1o 2o 3o
Some of the ketones such as ketoses (e.g. fructose) are of great biological

Amines Amines are the derivatives of ammonia (remember importance. Acetone is a commonly used solvent in organic labs and a nail Amides (peptidic bond) are essential in chemistry and biology as they are part of

NH3 from General chemistry). Replacing one hydrogen polish remover. many peptides and nucleobases.
R N R
R of ammonia with an alkyl group forms an amine with a
R = H or Alkyl general formula of R-NH2: Carboxylic acids
The combination of the carbonyl with OH gives the
H O
HN NH2
N R carboxylic acid functional group: O
NH2 OH
O O OH Acid Chlorides
OH OH
Acid chlorides are derivatives of carboxylic acids where the
Depending on how many alkyl groups are connected to the nitrogen, we have O
Acetic acid Butanoic acid Benzoic acid
R acidic proton is replaced by chlorine:
primary, secondary, and tertiary amines: O
Remember, however, that you cannot indicate them as two different Cl O O
Cl
functional groups! If they are together it is the carboxy group. Cl Cl
NH2 N N
H
ketone carboxylic acid
1o 2o
These are very reactive and are mainly used in organic
3o O Wrong
O

R OH R OH synthesis.
alcohol
Carbonyl-containing functional groups Functional groups with two carbonyls
Esters
O O O
Having another alkyl group in place of the hydrogen of You may not see them as often, but acid anhydrides and imides are also important
C C C
R H R R R Cl O
R carboxylic acid, makes the esters: functional groups in organic chemistry:
O R'
Aldehydes Ketones Acid chlorides O R'
O O O O O O O N O
C
O O O
O O R O R' R R'
Carbonyl C C C
R OH R NH2 R OR Esters occurr both naturally and synthetically. Most esters have a characteristic Anhydride Imide

Carboxylic acids Amides Esters smell responsible for the aroma of fruits, flowers, and wine.
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