Organic chemistry

Nomenclature and homologous series of alkanes

Neptune

Incredibly much around us consists largely of carbon compounds.

Especially living beings consist of carbon molecules which are therefore also called organic molecules.
These organic molecules are - logically - the subject of organic chemistry.

You already know the valence bar notation,

which is often used to describe organic molecules.

However, because chemists do not always want to draw the whole molecule
to show what they mean (this can quickly lead to mistakes),
the chemists' organisation IUPAC has come up with a method to give each
of these molecules a unique name.

Single chained carbon atoms (with hydrogen atoms, so that the octet rule applies) form the
homologous series of alkanes. The first molecules formed in this way have trivial names,
which you unfortunately have to learn by heart.

CH4

methane ethane propane butane

With this knowledge you should be able to master the first level.

With Nomenclature Neptune, you can easily build

organic molecules in valence bar notation.

Simply place the corresponding building blocks

from the bottom bar into the construction field and connect Construction field
them by dragging. The hydrogen atoms are always
automatically added or removed.

You can delete bindings by dragging them again or you can Slide mode
drag bricks into the trash can in the lower left
corner to remove them. Binding mode

carbon
You are given the task of building certain molecules. building block Delete
When you're done, tap the check mark in the app.
With this knowledge you should get to Alkane - Level 4.

From five or more carbon atoms chained together,

the naming of the unbranched alkanes is based pentane pentagram Pentagon

on Greek numerals and is easier to remember. hexane hexagon

heptane hexane + C: "x" becomes "pt"

octane octave

nonane nine

decane decimeter decade (10 years)

undecane
}
Uno
+10

dodecane duet

Page 1 planetary-apps.com With this knowledge you should get to Alkane - Level 6.
 Nomenclature of
Nomenclature single-branched alkanes
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Alkanes may have side branches.

methane

butane
If you have such a molecule, you must always find the main chain first.
With branched alkanes the main chain is always the longest chain, even over corners.
In the example above the longest continuous chain is butane.

All chains attached to the main chain are called side chains. You name them by simply writing "-yl"
instead of the ending "-ane"
In the example, methyl is a side chain.
This name is made up of the stem of methane and the ending -yl.

Once you have the main chain and side chain(s),

all you have to do is determine the positions.
The numbering always goes from one end of the main chain
to the other. In principle, there are always two possibilities.
Here methyl would either be in position 2 or 3.

Select the numbering where the side chain has the lower position.
So here methyl would be in position 2.

The naming is then as follows:

[position]-[side chain name][main chain name]
So the name of the molecule above is 2-methylbutane.

With this knowledge you should get to Alkane - Level 12.

Another example:

Executive summary:
1. Main chain = find and name the longest chain
2. Find and name side chain (yl instead of an)
3. Number the main chain to create the smallest
position Main chain: nonane
4. Write side chain name as prefix with Side chains: propyl and methyl
position in front Possible numberings:
4 and 5 (from above) or 5 and 6 (from below)
Smallest positioning → 4 → from above
4-propyl and 5-methyl
alphabetically: M before P → methyl
before propyl
Arrangement:
5-methyl-4-propylnonane
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 Nomenclature of multi-branched alkanes
Nomenclature without duplications
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If you can name molecules with one side chain, more side chains are no problem.

Search for the main chain again.

If there are several possibilities for the longest chain,
choose the main chain with more side chains.
Name it and all side chains.

You choose the numbering so that the

first occurring position (no matter which side chain)
is as small as possible.
If there are several possibilities for this,
the second occurring position should be as small as
possible, and so on.
in the selection between 2 and 3 you take the numbering
that puts methyl at 2.

Sort the side chains by alphabet (without numbering) and write them separated by
hyphens before the name of the main chain.
Pay attention again: Only the first letter of the name is capitalized.
E for ethyl comes before M for methyl. So the name of the molecule is 4-ethyl-2-methylhexane.

With this knowledge you should get to Alkane - Level 12.

Another example:

Executive summary:
1. Find & name side chains
2. As small a position as possible for the Main chain: nonane
first side chain and all others after Side chains: propyl and methyl
3. Side chains sorted alphabetically Possible numberings:
before the names of the main chain
4 and 5 (from above) or 5 and 6 (from below)
Smallest positioning → 4 → from above
4-propyl and 5-methyl
alphabetically: M before P → methyl
before propyl
Arrangement:
5-methyl-4-propylnonane

Page 3 planetary-apps.com
 Possible problems with the nomenclature
Nomenclature of branched alkanes
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Several options for numbering

Sometimes there are two possible variants for the smallest possible position of the side chain.

Here you have to decide between 4-ethyl-3-methylethane

and 3-ethyl-4-methylethane depending on the direction
of the numbering.

In this case, the lower position of the side chain whose name is
further ahead in the alphabet is to be preferred.
E for ethyl comes before M for methyl, so ethyl gets the smaller position
3, so this molecule is called 3-ethyl-4-methylhexane.

With this knowledge you should get to Alkane - Level 16.

Side chains of the same name

Some molecules have several side chains that have the same name as methyl.
If this occurs, one saves some writing work and introduces a binding summarizing notation.

2-methyl

The name 2-methyl-3-methyl-5-methylheptane

is a bit too long for us. heptane

3-methyl 5-methyl
First write down all positions where the corresponding side chain occurs,
separated by commas.
Methyl is at positions 2,3 and 5, so you write 2,3,5.
Prefix Number of side chains

Between the positions and the names of the side chain there is a prefix, di 2
which you can see in the table on the right. The prefixes are nothing
new from five side chains on, they correspond to the names of the tri
corresponding long chains (e.g. octa for 8 side chains). 3
Of course you have to keep the name of the side chain itself.
With the prefix "tri" for 3 side chains you get "trimethyl" instead of just "methyl". tetra 4
Now name exactly as you would with only one side chain of a type.
With correct upper and lower case, the molecule at the top is thus: penta 5
2,3,5-trimethylheptane
... ...

Page 4 planetary-apps.com With this knowledge you should get to Alkane - Level 25.
 Nomenclature of unbranched alkenes
Nomenclature with one double bond
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What are alkenes?

Alkenes are hydrocarbon molecules which contain double bonds, i.e.

unsaturated hydrocarbons (= not only single bonds).

Position of a double bond 1 3 5

2 4
The position of a double bond corresponds to the
lower position of one of the atoms it connects.
Provided the numbering indicated,
the double bond is located here at position 2.

Numbering of the main chain (one double bond)

The main chain is numbered so that the position

of the double bond is as small as possible. 15 2 4 3 3 42 51

The double bond is either a position 3 or

at position 2, so the numbering goes from
right to left

Nomenclature

Name the molecule like an alkane, but replace ane with -[position]-ene.

With this knowledge you should be able to master the first level of the alkenes.

More examples:

eth-1-ene (= ethylene)

Executive summary:
1. Smallest possible position for double bond
2. Replace ane with -[position]-en pent-2-ene

pent-1-ene
(sometimes: pentene)

Page 5 planetary-apps.com
 Building alkenes
Nomenclature
Neptune

Simply select the double-binding tool before attaching a binding.

It is only available in levels where you actually need a double bind.
Slide mode
Single bond
Double bond

With this knowledge you should get to Alkene - Level 2.

Nomenclature of unbranched alkenes

with more than one double bond

Numbering of the main chain (several double bonds)

- Consider the positions of the double bonds 3 3

1 5 2 4 42 51
in both possible directions.
- The direction in which the position
of the first double bond is smallest is to be preferred. The position of the first double bond is 1 in
- If the first positions are identical, the positions both directions, so it depends on the position
of the second double bond are compared of the second double bond.
(analogous for the third, fourth, ...). It is either 3 or 2, so the numbering is from right
to left.

Nomenclature

- List the positions of the double bonds separated by commas.

- From the list of side chain prefixes, find the prefix matching the number of double bonds.
- If there are at least two double bonds in the main chain, you need a bond-a.
- Name the molecule as if it were an alkane and replace an with

[possible connection "a"]-[positions]-[prefixes]ene

Do not forget to put hyphens in front of the positions and in front of the prefix.

The example molecule above is therefore penta-1,2,4-triene.

Page 6 planetary-apps.com With this knowledge you should get to Alkene - Level 4.
 Nomenclature of branched alkenes
Nomenclature
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Finding the main chain

The longest chain with the most double bonds serves as the main chain.

The marked chain here is no longer the longest chain,

but the one with the most double bonds and therefore
becomes the main chain.

3-propylpenta-1,3-diene

Several options for numbering the main chain

1 4
If there are several possibilities, 2 3
2-methylbut-2-ene
the previous rules can be applied.
32
This principle will be repeated again and again. 4 1
One rule dominates, but if there are several possibilities,
the next more important rule is used.
The positioning of the double bonds is 2 in both
directions, but since the position options for the side
chain are 2 and 3, the main chain is numbered
from right to left.

Nomenclature
In comparison to the naming of branched alkanes, only the name of the main chain changes.

With this knowledge you should get to Alkene - Level 9.

More examples:

2,4-dimethylhexa-1,5-diene 2-Ethyl-3-propylbuta-1,3-diene

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 Nomenclature of unbranched alkynes
Nomenclature
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What are alkynes?

Alkynes are hydrocarbon molecules that contain triple bonds.

They behave exactly like the alkenes in terms of their names, only with the different ending yne.

Position of a triple bond

The position of a triple bond corresponds - as with alkenes - to the lower position of one of the atoms it
links.

Numbering of the main chain 2 6 44 6 2

The main chain is numbered in the same way as the

alkenes, i.e. in such a way that the position of the first 17 35 5 3 7 1
(second, third, ...) triple bond is as small as possible. The first triple bond is - independent of the
direction - at position 1, so the inner triple
bond is decisive for the numbering. For
those, positions 4 and 3. The smaller
position is preferred, so here the main chain
is numbered from right to left.

Nomenclature

Name the molecule like an alkane, but replace

-[possibly connection "a"]-[positions separated by commas]-[prefix from the table]yne.

With this knowledge you should be able to master the first two levels of the alkynes.

25 43 61
Numbering of the main chain for double bonds

Number the main chain so that the first (second, third, ...)
position of multiple bonds (whether double or triple
bonds) is as small as possible.
If there are still both possibilities for numbering, ignore
the triple bonds and determine them only by the double
bonds.
1 6 34 52
The first multiple bond is - regardless of the
direction - at position 1, so the inner
multiple bond is decisive for the numbering.
for those, positions 3 and 3 are possible. If
the possible positions were different, the
numbering would be clear, but as with
alkenes, it only has to be determined
according to the double bonds. So the
numbering here goes from left to right.

Naming with any multiple bonds

Name the molecule like an alkene and simply add the alkyne ending at the end:
-[Items separated by commas]-[Prefix from table]yne

Page 8 planetary-apps.com With this knowledge you should get to Alkynes - Level 3.
 Nomenclature of branched alkynes
Nomenclature
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Finding the main chain

The main chain can be found as follows:

- Find the chains with the most multiple bonds.
- Take the longest one.
- If there are still several possibilities for the main chain,
choose the one with the most double bonds. Although the marked chain is not the
longest, it is the longest chain with the
most double bonds (one) and thus the
main chain of the molecule.

Nomenclature This molecule is therefore called 3-

propylhept-1-ene.
In comparison with the naming of denied alkenes, only
the main chain name changes.

2.
1.

3.

All three options shown here have the

same number of multiple bonds. Main
chain 1 has only length 5, so 2 and 3
remain to choose from. Main chain 3 has
more double bonds (one) in this selection,
so the main chain of the molecule shown
is chain 3.
Multiple bonds in side chains have not yet been explained;
therefore we cannot yet name this molecule.

With this knowledge you should get to Alkynes - Level 8.

More examples:

2,3-Dipropylhexa-1,3-dien-5-yne
6-methyl-3-propylhept-1-en-4-yne

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 Nomenclature of
Nomenclature saturated alcohols
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-
What are alcohols?
OH
Hydroxy group
Alcohols are hydrocarbons with at least one hydroxy group.
(but must be bound to C)

Finding the main chain

Similar to alkenes and alkynes, this time the longest

chain with the most attached hydroxy groups is
sought for alcohols.
Again, under certain circumstances, the longest chain
may not become the main chain because fewer hydroxy
groups are bound to it than to another (see example). Although the longest chain is heptane, the
hydroxy groups ensure that the main chain
is the marked one.

Numbering of the main chain

The numbering of the main chain also works in exactly

the same way as for alkenes or alkynes: Consider the
possible positions of the hydroxy group(s) - that is, the 1 4 23 41

positions of the carbon atoms to which they are 32

attached - and take the direction that the smaller first Possible positions for the hydroxy groups
(second, third, ...) position has. here are 2,4 or 1,3, so the chain is
numbered from right to left.

Nomenclature

Name alcohols exactly as before and add a suffix as with unsaturated hydrocarbons:

[name of the alkane]-[positions separated by commas]-[prefix from the table]ol

In contrast to the naming of alkenes and alkynes, the ending of an alcohol does not replace the ending
on the alkane.

Also, note that the "e" at the end of the name of the alkane name is dropped, so you will have an
ending of -an instead of -ane.

With this knowledge you should get to Alcohols - Level 4.

More examples:

butan-2-ol methan-1-ol pentan-2,3,4-triol

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 Nomenclature of
Nomenclature unsaturated alcohols
Neptune

2
Finding the main chain

Even with unsaturated alcohols, the main chain is

the longest chain with the most bound hydroxy
groups. Multiple bonds have a lower priority than
hydroxy groups. Therefore, the presence of a 1
multiple bond influences the finding of the main 3
chain only if there would otherwise be several
possibilities to find a main chain with the same
number of hydroxy groups. In this case, the main
chain finding rule for alkenes and alkynes is The chains 1-2, 2-3 and 1-3 all have the same
applied for the remaining possibilities. If this does number of bound hxdroxy groups (2), but
not yield a clear result, only the length of the chain different lenghts and different numbers of
is important. If this does not yield a result either, multiple bonds. After the number of hydroxy
the positions of the first (second, third, ...) hydroxy groups, the number of multiple bonds is
group are kept as small as possible, then those of most important, which makes the chain 1-3
the first (second, third, ...) multiple bond and so on. presipitate. The remaining chains 1-2 and 2-
3 both have exactly one multiple bond and
are of equal length. If they are numbered
correctly, the positions of the hydroxy groups
in chain 1-2 (or better: 2-1) are 1 and 4; in
chain 2-3 (better: 3-2) they are 1 and 6, so
chain 1-2 is the main chain and is numbered
from 2 to 1.

Nomenclature

Name again as you would name an alkene or alkyne and simply append the ending for alcohols.
If there is a multiple bond in the main chain, the ending at the stem alkane is dropped again,
otherwise it remains.
By the way: The possible endings are in this order, en, in and ol, because they correspond to the order of the respective priorities.

With this knowledge you should get to Alcohols - Level 9.

More examples:

3,4,5-trimethylhex-3-en-1-yne-1,6-diol 2,3-diethyl-4-methyloct-3-en-5-yne-1,7-diol

Page 11 planetary-apps.com
 Nomenclature of aldehydes
Nomenclature
Neptune

What are aldehydes?

O
Aldehydes are hydrocarbons with at least one formyl group. C
H
Formyl group
(without C)

Finding and numbering the main chain

The Formyl group has a higher priority than all previous characteristic groups. Thus, the criteria for
the main chain are now: number of formyl groups, number of hydroxy-G., number of multiple bonds,
chain length, number of double bonds, smallest possible positions for characteristic groups with the
highest possible priority

Likewise, one tries to have the lowest possible positions for the first (second, ...) formyl group; then,
if this does not lead to a clear main chain, one applies the selection criteria for alcohols to the other
possibilities, etc.

Nomenclature

Since the formyl group (for us for the time being) can only be at the end or ends of the main chain anyway, it
is not necessary to specify a position for its corresponding ending. Just add to the name the
molecule would have if it were a normal carbon atom with bound hydrogen atoms, al (or dial at
both ends in the case of formyl groups).

Special feature for hydroxy groups

Once a formyl group is present in a molecule, hydroxy groups are no longer identified in the name by
a suffix (which appears at the back of the name) but by a prefix at the front.
When naming them, you treat them like normal side chains called Hydroxy and sort them
alphabetically into possible remaining prefixes (side chains).

With this knowledge you should get to Aldehyde - Level 15.

Examples:

3-ethylpentanal 5-hydroxy-3,4-dimethylpent-3-enal 2-ethyl-3-hydroxyhex-3-endial

Page 12 planetary-apps.com
 Nomenclature of ketones
Nomenclature
Neptune

What are ketones? O

Ketones are hydrocarbons with at least one oxo group. C
Oxo group
(without C)

Finding and numbering the main chain

The oxo group has a higher priority than all previous characteristic groups except the formyl group.
This results in the main chain determination and numbering according to priorities.

Designation

The oxo group needs specified positions again. So simply append the corresponding ending to the
name again, this time -[comma-separated positions]-[prefix]one.

Build ketones

To build ketones in the nomenclature helper, simply use the building block for aldehydes and bind it
to two neighbouring C atoms.

Special feature for hydroxy groups

Just like hydroxy groups in aldehydes, hydroxy groups in ketones are named as prefix.

Special feature in aldehydes

In aldehydes, oxo groups are no longer called suffixes, but also prefix oxo and are treated similar to
side chains or hydroxy groups (alphabetical sorting together with the side chains).

With this knowledge you should get to Ketone - Level 12.

Examples:

hept-6-en-2,3,5-trione 4-hydroxy-3-propylhexan-2-one 5-ethyl-3-hydroxy-4-oxohept-2-endial

Page 13 planetary-apps.com