Nomenclature Alkanes Alkenes Aromatics

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					EES 4200 Nomenclature Worksheet for Alcohols, Alkyl Halides, Alkenes, and
Aromatics

Please also refer to your textbooks (Ouellette and Banks) for more detailed
explanations of IUPAC nomenclature of these compound classes.

Alcohols
                                   Name: 1-pentanol
H3C
                                   Note: Start counting carbons from the end that results in the
                                   lowest number for the carbon with the hydroxyl group. In this
                                   case, this carbon is the 1-carbon! This is a terminal, or primary,
                          OH       alcohol.

H3C
                                   Name: 3-pentanol

      HO            CH3            Note: Regardless of the direction of the counting, the third
                                   carbon is the one bearing the hydroxyl group.

            CH3
                                   Name: 2-methyl-3-pentanol
H3C
                                   Note: The position of the hydroxyl group dictates the sequence of
                                   counting carbons. Always strive for the lowest numbers; therefore, this
      HO            CH3            is NOT 4-methyl-2-pentanol. The –OH group takes precedence in
                                   numbering and should always be the lowest possible number.

   OH
                        Name: cyclohexanol

                        Note: The “1-“ is not required since the C with the
                        hydroxyl group is automatically assigned the “1” position.



   OH
                            Name: 3-isobutylcyclohexanol

                            Note: Again, since the C with the hydroxyl group is always the “1” carbon,
                            the “1-“ designation is not necessary in front of the “cyclohexanol.” Note that
                            the counting around the ring should proceed in a way that results in the lowest
                            number for the other substituents.
      H3C         CH3
          OH                    Name: 1-methyl-1,4-pentanediol
H3C
                                Note: This is a di-substituted alcohol. Note the “diol” on the
                                end, and the 2 numbers that signify positions of both hydroxyl
                                groups. Note that the numbers should be the lowest as
                         OH     possible!



Alkyl Halides


                                        Name: 1-chlorohexane

H3C                             Cl      Note: Always strive to obtain the lowest number
                                        possible.



                    Br
                                        Name: 3-bromo-1-chlorohexane

                                        Note: Present the substituents in alphabetical order.
H3C                             Cl      Strive for the lowest numbers possible. Therefore,
                                        this would NOT be 4-bromo-6-chlorohexane.


                    Br

                                      Name: 4-bromo-6-chloro-3-hexanol
H3C                             Cl
                                      Note: Recall that the –OH group takes precedence for
               OH                     alkyl groups and halogens.




Alkenes


H3C
                                      Name: 2-hexene

                                      Note: The first C of the C=C is used in the numbering
                                      scheme. Always use the lowest number possible.
                              CH3




                                                                                                 2
H3C
                          CH3
                                                  Name: 4-methyl-2-hexene

                                                  Note: The –ene group has precedence over the
                                                  alkyl group (and also over halogens). Thus, the first
                                       CH3
                                                  C of the C=C should have the lowest possible
                                                  number.



H3C
                          CH3                            Name: 3-methyl-1,4-hexadiene

                                                         Note: Note the addition of the “diene” at the end of the
                                                         name to signify two double bonds. Examples of other
                                                         di-substituted alkenes include butadiene, pentadiene,
                                       CH2
                                                         octadiene, dodecadiene, etc.



Aromatic Compounds

Some common names have been used to frequently that they have been
accepted as IUPAC names. Names of environmentally relevant compounds
include the following:
                       CH3                OH
                                                                        CH2
                                                                                                    O


                                                                                                    OH

Benzene             Toluene             Phenol              Styrene                  Benzoic Acid

You should know be able to recognize these compounds by structure and
name.

          Cl                  Name(s): 1,2-dichlorobenzene, or ortho-dichlorobenzene

                              Note: If the substituents are on neighboring carbons, they are
               Cl             designated as following ortho-substitution.

          Cl

                              Name(s): 1,3-dichlorobenzene, or meta-dichlorobenzene

                              Note: If the substituents are on the 1 and 3 carbons, they are
                              designated as following meta-substitution.
          Cl




                                                                                                           3
               Cl
                                             Name(s): 1,4-dichlorobenzene, or para-dichlorobenzene

                                             Note: If the substituents are on the opposite (1- and 4-)
                                             carbons, they are designated as following para-substitution.
Cl
                         Cl


Cl                                           Name: 1,3,5-trichlorobenzene


                         Cl

      Cl             Cl
                                             Name: Pentachlorophenol

Cl                            Cl             Note: The –OH group takes precedence. Since chlorines
                                             substitute all remaining carbons on the ring, no numbers are
                                             necessary! If one were to number this, however, the C with
      HO             Cl                      the –OH group is always the 1-C. (2,3,4,5,6-
                                             pentachlorophenol).

More Examples: Please do not forget that Ouellette has examples of
nomenclature for each of the compound classes (just check the chapters for
these classes). Banks will provide examples to work as well!

                                             Name: trichlorofluoromethane (also called CFC-11)
           F
                                             Note: What does this other nomenclature system mean?
Cl                  Cl                       For CFCs and HCFCs with one carbon, the right number denotes the number of
                                             fluorines and the left number denotes one more than the number of hydrogens. For
                                             CFCs and HCFCs (with hydrogens) with more than one carbon, the far right
       Cl                                    number is the number of fluorines, the middle number is one less than the number
                                             of carbons, and the left number is one more than the number of hydrogens. Can
                                             you draw one representation of CFC-12 and CFC-134 (a replacement of CFC-12)?



HO
                                                                   Name: 4-buten-1-ol

                                                                   Note: The –OH rules over halogens and alkyl groups.
                                                                   Thus, the C with the –OH must be lower in number.
                                                                   Note the use of “en” and “ol” in the name.
                                                  CH2


                                   OH                          Name:    2-bromo-6-methyl-6-hepten-3-ol
H3C                                             CH3
                                                               Note: This one is loaded! Recall that the –OH must always
                                                               have the lowest designation possible. The longest chain must
                                                               include the C=C! Recall also that the alkene has precedence
           CH2                          Br
                                                               over the alkyl and halogen groups, which are then alphabetized
                                                               in front of the –en and –ol designations.

                                                                                                                      4

				
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