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Foundation Science Lecture 1A 2011

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Foundation Science Lecture 1A 2011 Powered By Docstoc
					 Foundation
   Science
  CHM403
 Foundation
Chemistry II
Organic Chemistry
    Lecture 1
 Naming Hydrocarbons
      (nomenclature)




Hydrocarbons: IUPAC names
                    Objectives
1. What is organic chemistry?
2. What are hydrocarbons? What structural features identify
    alkanes? Alkenes? Alkynes? Aromatic hydrocarbons?
3. How are alkanes, alkenes, alkynes, and aromatic hydrocarbons
    named using IUPAC nomenclature?
4. What are the physical and chemical properties of alkanes,
    alkenes, alkynes, and aromatic hydrocarbons?
5. What is an alkyl group?
6. What are some products from reactions of alkanes? How are
    they formed?
7. What are the major reactions of alkenes? What are the
    products of those reactions?
           Division of Organic
                Chemicals


                        Groupings of Organic Compounds


                               Organic Comounds


        Aliphatic compounds                         Aromatic compounds
contain straight or branched chains or     carbon-based rings or multi-rings with
rings containing single carbon bonds     alternating single & double carbon bonds
            Introduction
• Organic chemistry is the study of
  carbon-containing compounds
   – especially compounds containing C-C
     bonds
• The field of organic chemistry is very
  important for a wide variety of reasons.
   – A huge number of carbon-containing
     compounds are known.
     • More than 16 million known compounds
     • About 90% of new compounds made each
       year contain carbon
            Introduction
• Most of the advances in the
  pharmaceutical industry are based on a
  knowledge of organic chemistry.
   – Many drugs are organic compounds
• Life as we know it is based on organic
  chemistry.
   – Most biologically important compounds
     contain carbon:
    • DNA, RNA
    • proteins
    • carbohydrates
           Hydrocarbons
• The simplest organic compounds are
  the hydrocarbons:
  – organic compounds that contain only
    carbon and hydrogen
  – four general types:
    • alkanes
    • alkenes
    • alkynes
    • aromatic hydrocarbons
          Hydrocarbons
• Alkanes:
  – hydrocarbons that contain only single
    bonds
• Examples:
  – Methane      CH4
  – ethane             H   H
                 H–C–C–H
                       H   H
          Hydrocarbons
• Alkenes:
  – hydrocarbons that contain a C = C
    double bond
    H2C = CH2 (ethylene)
• Alkynes:
  – hydrocarbons that contain a C   C triple
    bond
    H – C C – H (acetylene)
               Hydrocarbons
• Aromatic hydrocarbons:
  – contain a planar ring structure in which the carbon
    atoms are connected by a combination of both s and p
    bonds
           H
           C
   H-C         C-H
                            benzene
   H-C         C-H
           C
           H
    Naming: common vs. IUPAC
• Common names used in the 1800’s are still
  used for some compounds today:
       O                                    O
                H    C     C      H
       C            Acetylene               C
  H       OH                          H3C        CH3
  Formic acid                            Acetone
• The International Union of Pure and Applied
  Chemistry (IUPAC) was established in 1900s
• Frequent revisions to nomenclature
• Systematic method allows an infinite number of
  compounds to be named given a few rules
Mnemonic for first four prefixes

            First four prefixes
            •   Meth-   Monkeys
            •   Eth-    Eat
            •   Prop-   Peeled
            •   But-    Bananas
         Other prefixes

               • Pent-
  Decade


   ?
 Decimal
               • Oct-
               • Dec-
Decathalon • Hex-, Hept-, Non-
          Hydrocarbons
• Compounds containing only two
  elements
  – Carbon and hydrogen
    Alkanes: Structures and
            Names

• Objectives
  – Identify an alkane
  – Determine what an isomer of an alkane
    is
  – Identify different types of alkanes
             Alkanes
• Saturated Hydrocarbons
• Called saturated because each
  carbon is bonded to four other atoms
• Only single bonds
• Methane
• Ethane
• Propane
             Homology
• Related compounds
• Homologs
 – Have properties that vary in a regular
   and predictable manner
 – A manner of organization
 – Similar to P.T.
             Isomers
• Different compounds having the
  same molecular formula
• Butane
• Isobutane (isolated branched chain)
• Another name?
               Isomers
• Pentane
• Isopentane
• Neopentane
              Alkanes
• CnH2n+2
• Representation
  – Structural Formulas
  – Condensed Structural Formulas
  – Butane
          Alkyl Group
• A group of atoms that results when
  one hydrogen atom is removed from
  an alkane
• CnH2n+1
• Change –ane ending to –yl
• Methyl
• Ethyl
• Propyl
      IUPAC Nomenclature
• Define IUPAC
• Examine the rules for IUPAC naming
• Determine the correct names of
  alkanes
     IUPAC Nomenclature
• Geneva, Switzerland 1892
• International Union of Pure and
  Applied Chemistry
• IUPAC System of Nomenclature
  – (isobutane, isopentane are common
    names)
            IUPAC Rules
• 1. Name the longest chain in the
  parent compound. End in –ane.
  (Root name)
  – Number each carbon
  – See Example
• 2. Note the alkyl groups attached
• 3. Number the carbon that the
  group is attached to.
  – Must use the lowest number possible.
  – See Example
       IUPAC Rules Con’t
• 4. Use prefixes to indicate the
  amount of attached groups
  – See Example
• 5. If there are more than two or
  more different substituents, list them
  in alphabetical order. If at equal
  points, lower alphabetical order
  given lowest number
  – See Example
Name each of the following
      Name each of the following

A.                  B.



 C.


               D.
    Draw the structural
  formulas for each of the
         following

• 4-propylheptane
• 3-ethyl-2-methylpentane
• 3-isopropyl-3-methyloctane
     Properties of Alkanes
• Objectives
  – Determine the physical and
    physiological properties of alkanes
      Physical Properties
• Nonpolar
  – Insoluble in water
• Less dense than water
  – Less than 1.0g/ml
• Related to one another
  – See chart
• Boiling points
  – Increase with higher molar mass
   Physiological Properties
• Gases serve as anesthetics
• Liquid alkanes
  – Light liquids
  – Harmful to lungs

  – Heavy liquids
    • Mineral oil
    • Petroleum jelly
     Chemical Properties:
     Reactions of Alkanes
• Objectives
  – Determine the chemical properties of
    alkanes
      Chemical Properties
• Do not react with many laboratory
  agents
• Usually very flammable
  – Undergo combustion reactions

   CH4 + 2 O2  CO2 + 2 H2O + Heat

    2 CH4 + 3 O2  2 CO + 4 H2O
   (Harmful carbon monoxide reaction)
 Halogenated Hydrocarbons
• Objectives
  – Define what halogenated hydrocarbons
    are
  – Name halogenated hydrocarbons using
    common and IUPAC names
Halogenated Hydrocarbons
• Have one or more hydrogen atoms
  replaced by halogen atoms
  – Usually these are formed under UV light
    or very high temps




  – Results in an alkyl halide
        Common Names
• First part of name is alkyl group
• Second part is the halogen, ending in
  –ide
• Name these:
  – CH3CH2Br
  – (CH3)2CHCl
  – CH3I
  – CH3CH2CH2F
          IUPAC Names
• Rules similar to those used for
  naming alkanes
• Substitute in the prefixes fluoro-,
  chloro-, bromo-, and iodo-
Give the IUPAC name for each of
    the following compounds
          Cycloalkanes
• Define what a cycloalkane is
• Name and draw cycloalkanes
          Cycloalkanes
• Carbon atoms that are joined in a
  ring or circle
• Simplest: cyclopropane



• Another: cyclohexane
               Naming
• Add cyclo-
• Otherwise fairly similar to regular
  naming

• Draw structures for the following
  compounds
  – Cyclooctane
  – Ethylcyclohexane
  – 1,1,2-trimethylcyclobutane
    Draw these structures
• Cyclopentane
• 1-ethyl-2-methylcyclopentane
• 1-ethyl-1,2,5,5-
  tetramethylcycloheptane
               Alkenes
• Objectives
  – Define alkene
  – Name alkenes using IUPAC rules
             Alkenes
• End in -ene
• Unsaturated hydrocarbons




• Have a double bond (CH3=CH2)
           IUPAC Rules
1. Name the longest chain.
2. Indicate the position of the double
   bond with the lowest number
   possible.
3. Substituent groups named like
   alkanes




         5-methyl-2-hexene
Name each of the following
 Draw the structure for the
         following
• 3,4-dimethyl-2-pentene
• 3-ethyl-2-methyl-1-hexene
• 3-isopropylcyclopentene
     Properties of Alkenes
• Objectives
  – Determine the properties of alkenes
      Properties of Alkenes
• Similar to alkanes

• Occur widely in nature
• Ethylene
  – Triggers fruit ripening
  – Can be used artifically
• Others
  – Carotene
     • Vitamin A
  – Fruit coloring
    Chemical Properties:
    Reactions of Alkenes
• Define addition reactions
• Discuss hydrogenation and hydration
• Write equations for reactions
  between alkenes and other
  substances
       Addition Reactions
• One of the bonds in the double bond is
  broken and each of the involved carbon
  atoms then bonds to another atom or
  group




• Hydrogenation—addition of hydrogen to
  an unsaturated molecule
       Halogen addition
• Alkenes readily add halogen
  molecules
            Hydration
• Addition of water to an alkene
           Equations
• Write equations for the reaction
  between CH3CH=CHCH3 and each of
  the following
• H2
• Br2
• H2O (H2SO4 catalyst)
• Write equations for the reaction of   with
  each of the following.
• H2 (Ni catalyst)
• Cl2
• H2O (H2SO4 catalyst)
            Alkynes
• Define alkyne
• Name alkynes using IUPAC naming
  rules
                Alkynes
• Carbon atoms share 3 pairs of electrons,
  forming a triple bond
• Acetylene



• Alkynes have similar properties to those of
  alkanes and alkenes
• Naming is the same, except they end in
  -yne
THE END

				
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