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alcohol ol
aldehyde al
ketone one
This is a two carbon chain (eth) with no double bonds (an). There are
three chlorine atoms all on the first carbon atom.
First sort out the carbon skeleton. It's a three carbon chain with no
double bonds and a methyl group on the second carbon atom.
Notice that the whole of the hydrocarbon part of the name is written
together - as methylpropane - before you start adding anything else on
to the name.
This time the longest chain has 5 carbons (pent), but has a double
bond starting on the number 2 carbon. There is also a methyl group on
the number 3 carbon.
Note: You could equally well draw this molecule the other way round, but
normally where you have, say, 1-bromo-something, you tend to write the
bromine (or other halogen) on the right-hand end of the structure.
• ]
Alcohols
This is a two carbon chain with no double bond. The diol shows 2 -OH
groups, one on each carbon atom.
Note: There's no particular significance in the fact that this formula has the
carbon chain drawn vertically. If you draw it horizontally, unless you stretch the
carbon-carbon bond a lot, the -OH groups look very squashed together. Drawing
it vertically makes it look tidier!
Aldehydes
If you are going to write this in a condensed form, you write it as -CHO
- never as -COH, because that looks like an alcohol.
This time there are 5 carbons in the longest chain, including the one in
the -CHO group. There aren't any carbon-carbon double bonds. A
methyl group is attached to the number 2 carbon. Notice that in
aldehydes, the carbon in the -CHO group is always counted as the
number 1 carbon.
Ketones
Where
The old name for 2-hydroxypropanoic acid is lactic acid. That name
sounds more friendly, but is utterly useless when it comes to writing
a formula for it. In the old days, you would have had to learn the
formula rather than just working it out should you need it.
This time, not only is there a chlorine attached to the chain, but the
chain also contains a carbon-carbon double bond (en) starting on
the number 3 carbon (counting the -COOH carbon as number 1).
When the carboxylic acids form salts, the hydrogen in the -COOH
group is replaced by a metal. Sodium propanoate is therefore:
Notice that there is an ionic bond between the sodium and the
propanoate group. Whatever you do, don't draw a line between the
sodium and the oxygen. That would represent a covalent bond. It's
wrong, and makes you look very incompetent in an exam!
Salts are always named with the metal first - think of sodium
chloride or potassium iodide. So for consistency you would
need to reverse the formula of sodium propanoate -
NaOOCCH2CH3. But if you reverse the formula, you can't see
immediately that it is related to propanoic acid. So you learn to
live with the inconsistency.
Esters
An ester name has two parts - the part that comes from the acid
(propanoate) and the part that shows the alkyl group (methyl).
Make sure that you draw the ethyl group the right way round. A
fairly common mistake is to try to join the CH3 group to the oxygen.
If you count the bonds if you do that, you will find that both the CH3
carbon and the CH2 carbon have the wrong number of bonds.
Acid anhydrides
Draw two molecules of acid arranged so that the -OH groups are
next to each other. Tweak out a molecule of water - and then join
up what's left. In this case, because you want propanoic anhydride,
you draw two molecules of propanoic acid.
Amides
The old name for this would have been methyl cyanide. You might
think that that's easier, but as soon as the chain gets more
complicated, it doesn't work - as the next example shows.
Primary amines
a.
b.
c. (CH3)2CHCH2CH2CH2CHCH2
d.
Solution:
a. This consists of a six-membered ring, so the root is cyclohex. There are no double or
triple bonds, nor any elements but carbon and hydrogen, so the suffix is ane, making
cyclohexane. There is a branch with a one-carbon chain, which adds a methyl prefix. You
would start numbering at the end as close to the branch as possible. However, since this is a
cyclic compound, there is no end, so you would start at the branch. Since there is only one
branch, the numbering is redundant. The best name is methylcyclohexane, but 1-
methylcyclohexane is acceptable.
b. The longest chain has five carbons, making the root word pent. There are no carbon–
carbon double bonds, so pent is followed by an to make pentan. The functional group is a
ketone, so the suffix is one—making pentanone. The location of the functional group needs to
be identified. If you start numbering the compound (at either end), the functional group is on
carbon 3 making the full name 3-pentanone.
c. This longest chain is seven carbons long. It branches at the end. There is a double
bond at the other end. The seven-carbon chain makes it hept. The double bond adds hepten.
Since there is no other functional group, this makes it heptene. The double bond starts with an
end carbon, so that carbon is carbon number 1, and so 1-heptene. If you continue numbering
the carbons, the branch is on carbon 6. The branch has one carbon, a methyl. The name is 6-
methyl-1-heptene.
d. The longest chain is six carbons long, although there are three ways to make a
six-carbon chain. The root word is hex. The best choice is the chain that
includes the functional groups. In this example, the only functional group is an
alkene. Thus hexene. The chain is numbered, so that the functional group will
have the lowest value. The longest chain, numbered in that manner, would be
Either system will give the same name. The alkene is at carbon 2. There is one
carbon branch (methyl) at carbon 2 and a two-carbon one (ethyl) at carbon 3.
Therefore the name would be 1-methyl-2-ethyl-2-hexene.
When naming ethers, name either side of the oxygen using the rules above and a yl
suffix. String the two pieces together as separate words and add the third word, ether,
at the end. If both pieces are the same, use the name only once with the prefix di.
(e.g., dimethyl ether, not methyl methyl ether.)
Name each carbon chain attached to the nitrogen according to the preceding rules,
ending with the suffix yl. String each piece together as one word ending with amine.
If two pieces are the same, use the prefix di rather than repeating the name. If three
pieces are the same, use the prefix tri rather than repeating the name (as with ethers).
>> Example 2
a. CH3CH2OCH2CH2CH2CH3
b. (CH3CH2)2NH
c. CH3NH2
d. CH3OCH3
Solution:
a. This is an ether. One side of the oxygen has two carbons (ethyl) and the other has
four carbons (butyl). Therefore the name of the compound is ethyl butyl ether.
b. This is a secondary amine (it has a nitrogen attached to two carbons). The carbon
chains attached to the nitrogen are the same and have two carbons (ethyl), so the name of this
compound is diethylamine.
c. This is a primary amine. The one-carbon group is a methyl. Therefore the name of
this compound is methylamine.
d. This is an ether. The groups on either side of the oxygen are both methyl groups.
Therefore the name of this compound is dimethyl ether.
>> Example 3
a. 2,2-dimethylbutane
b. 3-propyl-5-hexynal (hexanynal)
c. 1-octanol
d. tripropylamine
e. 3-methylpentanoic acid
f. 5-ethyl-2-heptyne
Solution:
a. The butane is a four-carbon chain. There are two methyl (one-carbon) groups
on the second carbon.
CH CH CH CH CH CH CH CH OH
3 2 2 2 2 2 2 2
d. tripropylamine. The amine is a nitrogen that has three bonds. There are three
propyl groups attached to the amine, so there is no space for other hydrogens.
All the groups are the same (tri) and have three carbons (propyl). The structure
could be written as
(CH CH CH ) N or
3 2 2 3
e. 3-methylpentanoic acid. There are five carbons in the chain (pent), no double or triple
bonds (an), and a carboxylic acid at the end (oic acid). Carboxylic
This is only an issue for alkenes. In addition, if the groups attached to one of the
carbons in the double bond are the same, there are no geometric isomers.
The prefixes cis and trans are used when one group on the carbons opposite the
double bond is the same. If those groups are on the same side, it is a cis isomer; if
they are on opposite sides, a trans isomer.
>> Example 4
Identify the following as cis and trans isomers. Name each compound.
a.
b.
c.
Solution:
a. The group that is the same is the H group. It is on the same side (bottom) of
the double bond; therefore it is a cis isomer.
The longest carbon chain is from the upper left to the upper right, seven
carbons (hept). The double bond (en) is between the 3 and 4 carbons (3). As
above, it is the cis isomer. Consequently, the name is cis-3-heptene.
b. The group that is the same on either side of the double bond is CH CH (ethyl).
3 2
The longest chain is again from the upper left to the upper right, and seven
carbons long (hept). The double bond is between the 3 and 4 carbons (3- and
ene). There is also a two-carbon branch from carbon 4. So the name is trans-
4-ethyl-3-heptene.
c. The group that is the same is the ethyl group on the carbon to the right.
Because those are the same carbon, this compound does not have a geometric
isomer.
The longest chain is from the lower left to the upper or lower right. It doesn't
matter; thelength will be nine carbons (non). The double bond (en) is closer to
the right end, so the numbering should start from there. That makes the double
bond between carbons 3 and 4. There is also a two-carbon branch on carbon 3.
The name is 3-ethyl-3-nonene.