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ALKANES The following table contains the systematic names for the first twenty straight chain alkanes.

It will be important to familiarize yourself with these names, as they will be the basis for naming many other organic molecules throughout your course of study. Names ofxx Straight Chain Alkanes Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Undecane Dodecane Tridecane Tetradecane Pentadecane Hexadecane Heptadecane Octadecane Nonadecane Eicosane Alkyl Groups Molecular Formula CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 C11H24 C12H26 C13H28 C14H30 C15H32 C16H34 C17H36 C18H38 C19H40 C20H42

we can use the prefix iso-. The prefix will be placed in front of the alkane name that indicates the total number of carbons. Examples to use isopentane which is the same as 2-methylbutane isobutane which is the same as 2-methylpropane To assign the prefixes sec-, which stands for secondary, and tert-, for tertiary, it is important that we first learn how to classify carbon molecules. If a carbon is attached to only one other carbon, it is called a primary carbon. If a carbon is attached to two other carbons, it is called a seconday carbon. Atertiary carbon is attached to three other carbons and last, a quaternary carbon is attached to four other carbons. Examples to use 4-sec-butylheptane (30g) 4-tert-butyl-5-isopropylhexane (30d); if using example, may want to move sec/tert after iso disc The prefix neoExamples to use neopentane this

Alkanes can be described by the general formula CnH2n+2. An alkyl group is formed by removing one hydrogen from the alkane chain, and is described by the formula CnH2n+1. The removal of this hydrogen results in a stem change from -ane to -yl. Take a look at the following examples. The same concept can be applied to any of the straight chain alkane names provided in the table above.

neoheptane Alkoxy Groups Alkoxides consist of an organic group bonded to a negatively charged oxygen atom. In the general form, they are written as RO-, where R represents the organic substituent. Similar to what we saw with alkyl groups above, the concept of naming alkoxides can be applied to any of the straigt chain alkanes provided in the table above.

Using Common Names with Branched Alkanes Some branched alkanes have common names that are still widely used today. These common names make use of prefixes such as iso-, sec-, tert-, andneo-. The prefix iso-, which stands for isomer, is commonly given to 2-methyl alkanes. In other words, if there is methyl group located on the second carbon of a carbon chain,

Three Basic Principles of Naming

1. 2.

Choose the longest, most substituted carbon chain containing a functional group. A carbon bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substitute present must have the lowest possible number. Take alphabetical order into consideration; that is, after applying the first two rules given above, make sure that your substitutes and/or functional groups are written in alphabetical order.

3.

Example In this example, there is no need to utilize the third rule. Since the two substitutes are identical, neither takes alphabetical precedence with respect to numbering the carbons. This concept will become more clear in the next example. Example

Rule #1 Choose the longest, most substituted carbon chain containing a functional group. This example does not contain any functional groups, so we only need to be concerned with choosing the longest, most substituted carbon chain. The longest carbon chain has been highlighted in red and consists of eight carbons. Rule #1 Choose the longest, most substituted carbon chain containing a functional group. This example contains two functional groups, bromine and chlorine. The longest carbon chain has been highlighted in red and consists of seven carbons.

Rule #2 Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substitute present must have the lowest possible number. Since this example does not contain any functional groups, we only need to be concerned with the two substitutes present, that is, the two methyl groups. If we begin numbering the chain from the left, the methyls would be assigned the numbers 4 and 7, respectively. If we begin numbering the chain from the right, the methyls would be assigned the numbers 2 and 5. Therefore, to satisfy the second rule, numbering begins on the right side of the carbon chain as shown below. This gives the methyl groups the lowest possible numbering.

Rule #2 Carbons bonded to a functional group must have the lowest possible carbon number. If there are no functional groups, then any substitute present must have the lowest possible number. In this example, numbering the chain from the left or the right would satisfy this rule. If we number the chain from the left, bromine and chlorine would be assigned the second and sixth carbon positions, respectively. If we number the chain from the right, chlorine would be assigned the second position and bromine would be assigned the sixth position. In other words, whether we choose to number from the left or right, the functional groups occupy the second and sixth positions in the chain. In order to select the correct numbering scheme, we need to utilize the third rule.

Rule #3 After applying the first two rules, take alphabetical order into consideration. Alphabetically, bromine comes before chlorine. Therefore, bromine is assigned the second carbon position and chlorine is assigned the sixth carbon position.

difference principle. If we number the chain from the left, bromine, the methyl group and chlorine would occupy the second, fifth and sixth positions, respectively. This is illustrated in the second drawing below. If we number the chain from the right, chlorine, the methyl group and bromine would occupy the second, third and sixth positions, respectively. This is illustrated in the first drawing below. The position of the methyl, therefore, becomes a point of difference. In the first drawing it occupies the third position. In the second drawing it occupies the fifth position. To satisfy the second rule, we want to choose the numbering scheme that provides the lowest possible numbering of this substitute. Therefore, the first of the two carbon chains shown below is correct.

Example

So the first numbering scheme is the one to use

Rule #1 Choose the longest, most substituted carbon chain containing a functional group. This example contains two functional groups, bromine and chlorine, and one substitute, the methyl group. The longest carbon chain has been highlighted in red and consists of seven carbons.

Once you have determined the correct numbering of the carbons, it is often useful to make a list including functional groups, substitutes, as well as the name of the parent chain. Parent chain: heptane 2-Chloro 3-Methyl 6-Bromo 6-bromo-2-chloro-3-methylheptane Rule #2 Carbons bonded to a functional group must have the lowest possible carbon number. After taking functional groups into consideration, any substitutes present must have the lowest possible carbon number. This particular example illustrates the point of Problems

2.

Number the carbon atoms of the longest continuous chain, starting at the end closest to the double bond. Thus,

3.

is numbered from right to left, placing the double bond between the second and third carbon atoms of the chain. (Numbering the chain from left to right incorrectly places the double bond between the third and fourth carbons of the chain.)

4.

The position of the double bond is indicated by placing the lower of the pair of numbers assigned to the double-bonded carbon atoms in front of the name of the alkene. Thus, the compound shown in rule 2 is 2-pentene.

5.

The location and name of any substituent molecule or group is indicated. For example,

Alkenes: Nomenclature

Alkenes are normally named using the IUPAC system. The rules for alkenes are similar to those used for alkanes. The following rules summarize alkene nomenclature. 6. is 5-chloro-2-hexene. Finally, if the correct three-dimensional relationship is known about the groups attached to the doublebonded carbons, the cis or trans conformation label may be assigned. Thus, the complete name of the compound in rule 4 (shown differently here)

7.

1.

Identify the longest continuous chain of carbon atoms that contains the carbon-carbon double bond. The parent name of the alkene comes from the IUPAC name for the alkane with the same number of carbon atoms, except the -ane ending is changed to -ene to signify the presence of a double bond. For example, if the longest continuous chain of carbon atoms containing a double bond has five carbon atoms, the compound is a pentene.

8.

is cis-5-chloro-2-hexene.

Compounds containing just carbons and hydrogens are the most basic compounds encountered in organic chemistry. These compounds are referred to as hydrocarbons. On the most basic level, hydrocarbons can be divided into three groups: those containing just single bonds, those containing one or more double bonds, and those containing one or more triple bonds. Before discussing how to name these compounds, it is instructive to examine how they are represented by chemists. Drawing Hydrocarbons Recall that when carbon makes four bonds, it adopts the tetrahedral geometry. In the tetrahedral geometry, only two bonds can occupy a plane simultaneously. The other two bonds point in back or in front of this plane. In order to represent the tetrahedral geometry in two dimensions, solid wedges are used to represent bonds pointing out of the plane of the drawing toward the viewer, and dashed wedges are used to represent bonds pointing out of the plane of the drawing away from the viewer. Consider the following representation of the molecule methane:

chemistry, hydrocarbons can be represented in a shorthand notation called a skeletal structure. In a skeletal structure, only the bonds between carbon atoms are represented. Individual carbon and hydrogen atoms are not drawn, and bonds to hydrogen are not drawn. In the case that the molecule contains just single bonds (sp3 bonds), these bonds are drawn in a "zig-zag" fashion. This is because in the tetrahedral geometry all bonds point as far away from each other as possible, and the structure is not linear. Consider the following representations of the molecule propane:

Full structure of propane Skeletal structure of propane

Only the bonds between carbons have been drawn, and these have been drawn in a "zig-zag" manner. Note that there is no representation of hydrogens in a skeletal Two dimensional representation of methane structure. Since, in the absence of double or triple bonds, carbon makes four bonds total, the presence of hydrogens is implicit. Whenever an insufficient number of bonds to a carbon atom are specified in the structure, it is assumed that In the above drawing, the two hydrogens connected by solid lines, as well as the carbon in the center of the molecule, exist in a plane (specifically, the plane of the computer monitor / piece of paper, etc.). The hydrogen connected by a solid wedge points out of this plane toward the viewer, and the hydrogen connected by the dashed wedge points behind this plane and away from the viewer. In drawing hydrocarbons, it can be time-consuming to write out each atom and bond individually. In organic the rest of the bonds are made to hydrogens. For example, if the carbon atom makes only one explicit bond, there are three hydrogens implicitly attached to it. If it makes two explicit bonds, there are two hydrogens implicitly attached, etc. Note also that two lines are sufficient to represent three carbon atoms. It is the bonds only that are being drawn out, and it is understood that there are carbon atoms (with three hydrogens attached!) at the terminal ends of the structure.

Alkane nomenclature When hydrocarbons contain only single bonds, they are called alkanes. Alkanes are named using a prefix for the number of carbon atoms they contain, followed by the suffix -ane. The following table lists the rules for naming alkanes. 7 Hept Heptane

Numb er of carbo n atoms

8 Prefi x Compou nd name Image

Oct-

Octane

Non-

Nonane

Meth -

Methane

Alkane nomenclature is straightforward; the only difficulties come if one of the hydrogen or carbon atoms on the molecule is replaced by another atom or group. When 2 EthEthane this takes place, the group which replaces the hydrogen or carbon is called a substituent. Since the only kind of molecules we've discussed so far are alkanes, let's consider the situation in which one of the Prop hydrogen atoms on an alkane has been replaced by another Propane alkane. Consider the following molecule, 3-methypentane:

But-

Butane

Skeletal structure of 3-methylpentane 5 Pent Pentane

Hex-

Hexane

Consider the long chain of five carbon atoms at the top of the image. If this were all that composed the molecule, it would simply be called pentane. However, one of the hydrogens on the carbon third from the end has been

replaced with an alkane, specifically methane. How are we to name this molecule?

prefixes are ignored when considering alphabetical order. Consider the following compound:

1.

First, we identify the longest chain of carbon atoms. We name this alkane. It will serve as the root name for the molecule. In the example above, the root name is pentane.

2.

Next, we number the carbon atoms, starting at the end that gives the substituent the lowest number. In the example above, we can count from either end and arrive at 3 for the substituent.

Skeletal structure of 4-ethyl-2,2-dimethylheptane

The longest carbon chain has seven carbon atoms, so the root name is heptane. Numbering from the right gives the lowest number to the first substituent. There are two methyl substituents at the second carbon atom, so we use the prefix 2,2-dimethyl. There is another substituent on the fourth carbon atom, so we use the prefix ethyl. Ethyl comes before methyl alphabetically, so we name the compound 4-ethyl2,2-dimethylheptane. Let's consider one final example, when the substituent is not a linear alkane. If the substituent is branched, we consider these branches to be substituents of the original

3.

Next, we name the substituent as if it were an independent alkane. However, we replace suffix -ane with -yl. This name will serve as the prefix. In the example above, methane is the substituent, so we call it methyl.

4.

The compound is named "numberprefixrootname". In the example above, the name is 3methylpentane

Let's try some more complicated examples. What happens if the alkane has more than one substituent? In this case, the rules above are followed, and the carbons on the longest chain are numbered to give the lowest number possible to one of the substituents. The substituents are then all named in the prefix, separated by a dash, in alphabetical order (e.g. 3-ethyl-2-methyl). If the same substituent is attached several times, the numbers of all carbon atom to which it is attached are repeated, separated by commas, before it to indicate the number of substituents. In addition, the prefixes di- (2), tri- (3), or tetra- (4) are used. The

substituent (confused yet?). The substituent's substituents must be named using the rules outline above. The final name of the original substituent is placed in parentheses. Consider the following molecule:

Alkyne nomenclature Hydorcarbons containing one or more triple bonds are called Alkynes. Alkynes are named using the same general procedure used for alkenes, replacing the suffix with -yne. If a molecule contains both a double and a triple bond, the carbon chain is numbered so that the first multiple bond gets a lower number. If both bonds can be assigned the same Skeletal structure of 5-(1-methylpropyl)nonane number, the double bond takes precedence. The molecule is then named "n-ene-n-yne", with the double bond root name preceding the triple bond root name (e.g. 2-hepten-4-yne). Alkynes: Nomenclature The longest chain of carbon atoms is clearly located at the bottom of the molecule. This chain gives it the root name nonane. The substituent is located at the second carbon atom. The substituent, however, is branched. If we were to name it alone, we would call it 1-methylpropane. But it is a substituent, so we must use the suffix -yl. The molecule is named 5-(1-methylpropyl)nonane. Alkene nomenclature Alkenes are hydorcarbons containing one or more double bonds. Alkenes are named using the same general naming rules for alkanes, except that the suffix is now -ene. There are a few other small differences: Although some common alkyne names, such as acetylene, are still found in many textbooks, the International Union of Pure and Applied Chemistry (IUPAC) nomenclature is required for journal articles. The rules for alkynes in this system are identical with those for alkenes, except for the ending. The following rules summarize alkyne nomenclature.

1.

Identify the longest continuous chain of carbon atoms that contains the carbon-carbon triple bond. The parent name of the alkyne comes from the IUPAC name for the alkane of the same number of carbon atoms, except the -ane ending is changed to - yne to signify the presence of a triple bond. Thus, if the longest continuous chain of carbon atoms containing a triple bond has five atoms, the

The main chain of carbon atoms must contain both carbons in the double bond. The main chain is numbered so that the double bond gets the smallest number. 2.

compound is pentyne. Number the carbon atoms of the longest continuous chain, starting at the end closest to the triple bond. Thus,

Before the root name, the number of the carbon atom at which the double bond starts (the smaller number) is written.

If more than one double bond is present, the prefixes di-, tri-, tetra-, etc. are used before the -ene, and (strangely) the letter "a" is added after the prefix for the number of carbon atoms. 3. is numbered from right to left, placing the triple bond between the second and third carbon atoms of the chain. (Numbering the chain from left to right

incorrectly places the triple bond between the third and fourth carbons of the chain.) 4. The position of the triple bond is indicated by placing the lower of the pair of numbers assigned to the triple-bonded carbon atoms in front of the name of the alkyne. Thus the compound shown in rule 2 is 2pentyne. 5. The location and name of any substituent atom or group is indicated. For example, the compound

19. To name alkynes as substituent groups, such as this molecule:

20.

21. First, count the longest parent chain. The longest parent chain is an octane. The substituent, located on carbon four, is an ethyne group. To name alkynes as substituents, you take the name, ethyne, and make it ethynyl. If the substituent was a three carbon chain with a triple bond, it would be called propynyl.

ALCOHOLS The following is list of some common primary alcohols based on the IUPAC naming system.

6. 7. 8.

is 5-chloro-2-hexyne. Nomenclature of Alkynes Alkynes are named similarly to alkenes. Much like alkenes, you change the ending of the molecule name to designate a triple bond. Instead of the -ane or the -ene, you use -yne. You number the carbon to the lowest possible carbon number.

Name Methanol

Molecular Formula CH3OH

9. 10. The above molecule is called 2-pentyne. 11. Alkynes have the lowest priority (other than alkanes, which are THE lowest). This means that when you have both a double bond and triple bond, the double bond gets the priority in numbering. Let's look at this molecule:

(methyl alcohol) Ethanol (ethyl alcohol) C2H5OH

12. 13. This molecule is called 1-penten-4-yne. 14. 15. The simplest possible alkyne is the two carbon triple bond, which would be called ethyne. However, in keeping with "historical" names, the name "acetylene" is popular. This isn't anything that you can deduce, it's one of the random names that organic chemists like to use. So, remember that this molecule, 16. 17. is called acetylene (although ethyne is still a good name to use). 18.

Propanol

C3H7OH

Butanol Pentanol

C4H9OH C5H11OH

Hexanol Heptanol

C6H13OH C7H15OH

Octanol

C8H17OH

Rules for naming the alcohols 1. Find the longest chain containing the hydroxy group (OH). If there is a chain with more carbons than the one containing the OH group it will be named as a subsitutent. Place the OH on the lowest possible number for the chain. With the exception of carbonyl groups such as ketones and aldehydes, the alcohol or hydroxy groups gets first priority for naming. When naming a cyclic structure the -OH is assumed to be on the first carbon unless the carbonyl group is present, in which case the later will get priority at the first carbon. When multiple -OH groups are on the cyclic strucuture, number the carbons on which the -OH. Remove e from the parent alkane chain and add ol. When multiple alcohols are present use di, tri, etc before the ol but after the parent name. ex) 2,3-hexandiol. IF the carbonyl group is present the -OH group is named as hydroxy, with the carbonyl group chaning the parent chain name so that it ends with al or one.

Cyclic alcohol (two -OH

2.

groups): diol Other functional group on the cyclic

cyclohexan-1,4-

3.

4.

5.

structure: 3-hexeneol (the alkene is in bold and indicated by numbering the carbon closest to the alcohol)

Ethane: CH3CH3 ----->Ethanol: (the alcohol found in beer, wine and other consumed sprits)

A complex alcohol: 4ethyl-3hexanol (the parent chain is in red and the substiuent is in blue)

Alkyl halides IUPAC nomenclature of alkyl halides Secondary alcohol: Other functional groups on an 2-propanol

12MAR The IUPAC rules permit alkyl halides to be named in two different ways, calledfunctional nomenclature. class In

nomenclature and substitutive

functional class nomenclature the alkyl group and the halide (fluoride, chloride, bromide, or iodide) are

designated as separate words. The alkyl group is named on the basis of its longest continuous chain beginning at the carbon to which the halogen is attached.

Substitutive nomenclature of alkyl halides treats the alcohol: 3-bromo-2-pentanol halogen as a halo-(fiuoro-, chloro-, bromo-, or iodo-) substituent on an alkane chain. The carbon chain is

numbered in the direction that gives the substituted carbon

The chain is numbered so as to give the halogen the lowest possible number Alkyl halide style:

The root name is based on the longest chain containing the halogen.

This root give the alkyl part of the name. The type of halogen defines the halide suffix, e.g. chloride The chain is numbered so as to give the halogen the lowest possible number. Examples

the lower number.

When the carbon chain bears both a halogen and an alkyl substituent, the two are considered of equal rank, and the chain is numbered so as to give the lower number to the substituent nearer the end of the chain.

IUPAC

Nomenclature Rules Functional group suffix = halide (i.e. fluoride, chloride, bromide, iodide) Substituent name = halo- (i.e. fluoro, chloro, bromo, iodo) Structural unit: haloalkanes contain R-X where X = F, Cl, Br, I Notes : Haloalkanes can also be named as alkyl halides despite the fact that the halogens are higher priority than alkanes. The alkyl halide nomenclature is most common when the alkyl group is simple. Haloalkane style: The root name is based on the longest chain containing the halogen. This root give the alkane part of the name. The type of halogen defines the halo prefix, e.g. chloro-

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