Naming And Drawing Hydrocarbons Study Guide
Iupac Naming And Formulae. Iupac Naming And Formulae 4.3 IUPAC naming and formulae (ESCKG) What is IUPAC naming? (ESCKH) In order to give compounds a name, certain rules must be followed. When naming organic compounds, the IUPAC (International Union of Pure and Applied Chemistry) nomenclature (naming scheme) is used. This is to give consistency to the names. It also enables every compound to have a unique name, which is not possible with the common names used (for example in industry). We will first look at some of the steps that need to be followed when naming a compound, and then try to apply these rules to some specific examples.
A good general rule to follow is to start at the end (the suffix) and work backwards (from right to left) in the name. Table 4.6: The prefix of a compound's name is determined by the number of carbon atoms in the longest chain that contains the functional group. Number the carbons in the longest carbon chain ( Important: If the molecule is not an alkane (i.e. Has a functional group) you need to start numbering so that the functional group is on the carbon with the lowest possible number). Start with the carbon at the end closest to the functional group. Look for any branched groups:. Name them by counting the number of carbon atoms in the branched group and referring to, these groups will all end in -yl.
Note the position of the group on the main carbon chain. If there is more than one of the same type of branched group then both numbers must be listed (e.g. 2,4 -) and one of the prefixes listed in must be used. Important: If the molecule is an alkane the branched group must be on the carbon with the lowest possible number. The branched groups must be listed before the name of the main chain in alphabetical order (ignoring di/tri/tetra). If there are no branched groups this step can be ignored. Table 4.8: Naming halogen atoms in organic molecules.
Give the halogen atom a number to show its position on the carbon chain. If there is more than one halogen atom the numbers should be listed and a prefix should be used (e.g.
3,4-diiodo- or 1,2,2-trichloro-). See for a list of the prefixes. The halogen atoms must be listed before the name of the main chain in alphabetical order (ignore di/tri/tetra).
If there are no halogen atoms this step can be ignored. Combine the elements of the name into a single word in the following order:. branched groups/halogen atoms in alphabetical order (ignoring prefixes). prefix of main chain.
name ending according to the functional group and its position on the longest carbon chain. Naming hydrocarbons (ESCKJ) Naming alkanes The suffix for an alkane is -ane. Worked example 1: Naming the alkanes. Look for any branched groups, name them and give their position on the carbon chain There are two methyl groups attached to the main chain. The first one is attached to the second carbon atom and the second methyl group is attached to the third carbon atom. Notice that in this example it does not matter how you have chosen to number the carbons in the main chain; the methyl groups are still attached to the second and third carbon atoms and so the naming of the compound is not affected. This group will be 2,3-dimethyl.
Look for any branched groups, name them and give their position on the carbon chain There is one methyl group attached to the main chain. If we number as shown in red (on the left) the methyl is attached to the fourth carbon atom.
If we number as shown in blue (on the right) the methyl is attached to the third carbon atom. After functional groups, the branched groups should have the lowest numbers possible. Therefore the blue numbering (on the right) is correct. The methyl is attached to the third carbon atom (3-methyl). There are four carbon atoms in the longest chain so the prefix is but. The functional group is an alkane, so the suffix is -ane. There is one branched group which is a methyl group and this is at position 2.
The molecule is 2-methyl butane. Note that in this example it does matter which way you number the chain as the branched group needs to have the lowest number possible and so the compound is not 3-methylbutane. Naming alkenes The suffix for an alkene is -ene. Worked example 6: Naming the alkenes. There is a triple carbon-carbon bond.
This compound is an alkyne and will have the suffix -yne. There are six carbon atoms in the longest chain, therefore the prefix will be hex. The triple bond is between the third and fourth carbon atoms regardless of how you number the chain (-3-yne). There are two branched methyl groups. Depending on the order of numbering they are either on the fourth carbon atom (left to right) or the second carbon atom (right to left).
The lower numbering is correct (right to left) and as there are two methyl groups this is 2,2-dimethyl. The molecule is 2,2-dimethylhex-3-yne. Draw the structural representation of the compound: The compound has a triple carbon-carbon bond, therefore it is an alkyne and the suffix is -yne. There are four carbon atoms in the longest chain so the prefix is but. There are no branched chains. The double bond occurs between the first and second carbon atoms. The compound is therefore but-1-yne or butyne.
Note that the way we number the carbon atoms matters. The double bond is given the lowest possible number and so this compound is not but-3-yne. Draw the structural representation of the compound: The compound has a double carbon-carbon bond, therefore it is an alkene and the suffix is -ene. There are three carbon atoms in the longest chain so the prefix is prop. There are no branched chains. The double bond occurs between the first and second carbon atoms. The compound is propene.
Note that the way we number the carbon atoms matters. The double bond is given the lowest possible number and so this compound is not prop-2-ene. Also, we do not include the 1 in the name as this is the only position that the double bond can occur in propene. Naming alkyl halides (ESCKK) All the same rules apply when naming the alkyl halides as for naming the hydrocarbons.
We will only be dealing with the haloalkanes (i.e. There are no other functional groups). The halogen atom is treated in the same way as a branched group. Worked example 12: Naming the haloalkanes. Draw the structural representation: There are halogen atoms and only single carbon-carbon bonds, therefore this is a haloalkane and the suffix is -ane. There are four carbon atoms in the longest chain containing all the halogen atoms, therefore the prefix is but. There is a fluorine atom attached to the first carbon atom (1-fluoro).
There are two iodine atoms attached to the second carbon atom (2,2-diiodo). These must be put in alphabetical order, ignoring any prefixes on the halogen atoms. F comes before i (1-fluoro-2,2-diiodo).
This molecule is 1-fluoro-2,2-diiodobutane Naming alcohols (ESCKM) The rules used to name the alcohols are similar to those already discussed for the hydrocarbons. The suffix of an alcohol is –ol (see ). Worked example 15: Naming the alcohols. Draw the structural representation of the compound: There is a hydroxyl group, therefore the compound is an alcohol and the suffix is -ol. There are four carbon atoms in the longest chain so the prefix is but. There are only single carbon-carbon bonds, therefore the prefix becomes butan.
There are no branched groups. The hydroxyl group is attached to the second carbon atom.
The molecule is 2-butanol or butan-2-ol. Note that the way we number the carbon atoms matters. The hydroxyl group is given the lowest possible number and so this compound is not butan-3-ol.
There is a hydroxyl group, therefore the compound is an alcohol and the suffix is -ol. There are five carbon atoms in the longest chain so the prefix is pent. There are only single carbon-carbon bonds, therefore the prefix becomes pentan. There are no branched groups. The hydroxyl group is attached to the second carbon atom. The molecule is 2-pentanol or pentan-2-ol.
Note that the way we number the carbon atoms matters. The hydroxyl group is given the lowest possible number and so this compound is not pentan-4-ol. There are two hydroxyl groups, therefore the compound is an alcohol and the suffix is -diol.
There are seven carbon atoms in the longest chain so the prefix is hept. There are only single carbon-carbon bonds, therefore the prefix becomes heptan. The hydroxyl groups are both attached to the third carbon atom (-3,3-diol). The branched methyl chain is attached to the fourth carbon atom.
The molecule is 4-methylheptan-3,3-diol. Note that the way we number the carbon atoms matters. The hydroxyl groups are given the lowest possible numbers and so this compound is not 4-methylheptan-5,5-diol. Naming carbonyl compounds (ESCKN) A carbonyl group consists of a carbon atom that is bonded to an oxygen atom through a double bond (C (= )O). There are many different functional groups that contain a carbonyl group. Naming aldehydes If the carbonyl group is on the end of the carbon chain, the organic compound is called an aldehyde. An aldehyde has the suffix -al.
Worked example 18: Naming aldehydes. Draw the structural representation: This compound contains a carbonyl group and an oxygen atom attached to two different carbon atoms. Therefore this is an ester and the suffix is -oate. There are two carbon atoms in the chain without the carbonyl group (from the alcohol), therefore this group is ethyl. There are two carbon atoms in the chain with the carbonyl group (from the carboxylic acid), therefore the prefix is ethan. There are no branched groups. This molecule is therefore ethyl ethanoate.
Draw the structural representation: There is a carbonyl group and a hydroxyl group attached to the same carbon atom. This compound must be a carboxylic acid and have the suffix -oic acid. There is one carbon atom in the longest chain therefore the prefix is methan. There are no branched chains (there can be no branched chains). This molecule is methanoic acid. Building molecules Using atomic model kits build molecules of butane, but-1-ene, but-1-yne, butan-1-ol, butanoic acid, butyl butanoate, butan-2-one, butanal.
If you don't have an atomic model kit remember that you can use jelly tots (or playdough) and toothpicks. Use different colour jelly tots to represent the different atoms and extra toothpicks to represent double and triple bonds. Identify the functional group in each of these molecules. Move the functional group around the molecule. You should find that you can do so with but-1-ene, but-1-yne and butan-1-ol. It will not be possible with butanoic acid and there is no functional group to move in butane.
Can you see that if you move the carbonyl group in butan-2-one you will either still get butan-2-one or you will get butanal? Similarly, when moving the carbonyl group in butanal you can only get butanal or butan-2-one. Build a model of the molecule below:. Compare this to butyl butanoate. What differences are there between these two molecules?
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Naming And Drawing Hydrocarbons Study Guide Answers
What similarities are there? What is the name of the new molecule?.
Continue by building different compounds for your friends. Make them identify the functional group, the number of carbon atoms and therefore the name of the compound. IUPAC naming.
Naming an organic compound requires several steps. What follows is a minimal outline.
Consult your textbook for more details and examples. Find the longest continuous chain of carbon atoms. This longest chain may not be written in a straight line. Name that longest chain with the appropriate alkane name. Find the substituents and name each of them with the appropriate group name. Number the carbons in the chain such that the lowest number is given to the group nearest one end of the chain.
Organic Chemistry Naming Hydrocarbons Pdf
List the groups alphabetically in front of the longest chain name. Precede each group name with a prefix indicating how many of them are present in the molecule. In front of the prefix, list the numbers of each group in the molecule and separate the numbers with a hyphen.