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Hydrocarbons

               Objectives

 Describe the bonding in hydrocarbons.

 Distinguish between straight-chain alkane
and branched-chain alkane.
Organic Chemistry
• Includes the Chemistry of      • Carbon compounds number
  virtually all carbon             more than a million, with
  compounds, regardless of         many valuable properties:
  their origin.
                                 • One main reason is carbon´s
• Before scientists believed       unique bonding ability.
  that organic compounds
  could only be sinthesized by   • The simplest of the organic
  organisms, but Friedrich         compounds are the
  Wöhler(1800-1882) refuted        Hydrocarbons .
  that theory in 1828.
Basic Principle of Carbon Bonding:
• Carbon has four (4)
  valence
  electrons, therefore will
  always form four
  covalent carbon-
  hydrogen bonds.

Note:
  Remembering this will
  help you complete and
  correct structures for
  organic molecules.
Types of Formulas:
• Structural Formulas:

   Convenient to write.
   Two-dimensional
    representations of
    three-dimensional
    molecules
Molecular Models:



Represent shapes
of molecules
more accurately
Carbon has the ability to make stable
 carbon-carbon bonds and to form
 chains. This is the main reason for
 the numerous carbon compounds.
   Carbon + Hydrogen→ Methane

      C + H2               CH4
Straight-Chain Alkanes:
• Contain any number of carbon atoms, one after the
  other, in a chain

• They always end in –ane

• To draw the structural formula for a straight-chain
  alkane, write the symbol for carbon as many times as
  necessary to get the proper chain length.

• Then, fill in with hydrogens and lines representing
  covalent bonds.

   – Each covalent bond is equivalent to two electrons.
Butane
Homologous Series:
The straight chain of alkanes are an example of
a homologous series.
  A group of compounds form a homologous series if
  there is a constant increase/increment of change in
  molecular structure from one compound in the
  series to the next.

The -CH2- group is the increment of change in
straight –chain alkanes.

As the number of carbons in the straight-chain
alkane increases, so does the boiling point and
their melting point.
• Molecular Formula:
• CH4 Methane
  • Complete Structural
         Formulas:
• Show all the atoms and
  bonds in a molecule.
                           Complete Structural Formula
  • Condensed Structural
           Formulas:
• Leave out some bonds
   and/or atoms from the
   structural formula.
   Although they do not
   appear, you must
   understand that these
   bonds and atoms are
                           Condensed Structural Formula
   there.
Nomenclature/ Naming System:
 IUPAC: International Union of Pure and Applied
Chemistry.
   All the names end in –ane.
   The root part of an alkane´s name indicates how many carbon
   atoms it contains.

Scientists also rely on a combination of systematic,
semisystematic, and common names to identify organic
compounds.


 Some organic compounds are best known for their
common names.
Basic Alkanes:
Branched-Chain Alkanes
• An alkane with one or more
  alkyl groups
  – An alkyl group is a
    hydrocarbon substituent
     • Substituent: an atom or group
       of atoms that can take the
       place of a hydrogen atom on a
       parent hydrocarbon molecule.
  – An alkyl group consists on an
    alkane with one hydrogen
    removed.
  – Sometimes referred to as
    radicals.
  – Change the suffix –ane from
    the parent structure to -yl
Rules for Naming Branched-Chain Alkanes:
1.   Find the longest chain of carbons in the molecule. We consider this
     the parent structure.

2. Number the carbons in the main chain sequence. Start at the end that
will give the groups attached to the chain the smallest numbers.

3. Add numbers to the names of the substituent groups to identify their
positions on the chain. These numbers become prefixes to the name of
the parent alkane.

4. Use prefixes to indicate the appearance of a group more than once in
the structure. Ex. Di-, tri-, tetra-; penta-, etc.

5. List the names of the alkyl substituents in alphabetical order.

6. Use proper punctuation. Commas( ,) are used to separate numbers,
hyphens(-) are used to separate numbers and words. The entire name is
written without spaces.
2,3,3-trimethylpentane
To draw the formula when given the name:
• With an alkane name and knowledge of the
  IUPAC rules, it is easy to reconstruct the
  structural formula.
• Steps:
1. Find the root word(ending in –ane) in the
   hydrocarbon name.
2. Number the carbons on this parent chain.
3. Identify the substituent groups. Attach the
   substituents to the numbered parent chain at
   the proper positions.
4. Add hydrogens as needed.
Properties of Alkanes:
Other Properties of Alkanes:

-They are non-polar
-Hydrocarbons of low molar mass tend to be
gases or low-boiling liquids.
-Non-polar organic molecules are insoluble in
water.
-Rule: “Like dissolves like”
   -Polar dissolves polar and non-polar dissolves
   non-polar.
   - Non-polar will never mix with a polar.
Practice Problems: Name the following compounds
Unsaturated Hydrocarbons:

                 Objectives:

• Explain the difference between unsaturated
  and saturated hydrocarbons.
• Differentiate between the structures of
  alkenes and alkynes.
Alkenes
• Alkanes are said to be saturated compounds
  because they contain a maximum number of
  hydrogens.

• Alkenes and alkynes, on the other
  hand, contain double and triple bonds
  respectively.

• They are said to be unsaturated compounds
  because they contain fewer number of
  hydrogens in their structure.
IUPAC Naming System for Alkenes:
1. Find the longest chain in the molecule that
   contains the double bond. This is the parent
   alkene. As a base, you use the base name of
   alkanes and change the suffix –ane to –ene.
2. The chain is numbered in the same way that
   alkanes, except that the carbon atoms of the
   double bond get the lowest possible numbers.
3. Substituents on the chain are named and
   numbered in the same way they are for alkanes.
   Ethene and propene are the simplest alkenes.
Ethene 3D
 Ethene 2D:




Propene 2D     Propene 3D
Name the following alkenes:
Alkynes:
• Are hydrocarbons
  containing carbon-
  carbon triple covalent
  bonds
• They are unsaturated
  compounds
• They are not plentiful in
  nature
• The simplest alkynes
  are:
  ethyne, propyne, butyn
  e
• Ethyne is commonly called
  acetylene.
Name the following compound:
Hydrocarbons

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Hydrocarbons

  • 1. Hydrocarbons Objectives Describe the bonding in hydrocarbons. Distinguish between straight-chain alkane and branched-chain alkane.
  • 2. Organic Chemistry • Includes the Chemistry of • Carbon compounds number virtually all carbon more than a million, with compounds, regardless of many valuable properties: their origin. • One main reason is carbon´s • Before scientists believed unique bonding ability. that organic compounds could only be sinthesized by • The simplest of the organic organisms, but Friedrich compounds are the Wöhler(1800-1882) refuted Hydrocarbons . that theory in 1828.
  • 3. Basic Principle of Carbon Bonding: • Carbon has four (4) valence electrons, therefore will always form four covalent carbon- hydrogen bonds. Note: Remembering this will help you complete and correct structures for organic molecules.
  • 4. Types of Formulas: • Structural Formulas:  Convenient to write.  Two-dimensional representations of three-dimensional molecules
  • 5. Molecular Models: Represent shapes of molecules more accurately
  • 6. Carbon has the ability to make stable carbon-carbon bonds and to form chains. This is the main reason for the numerous carbon compounds. Carbon + Hydrogen→ Methane C + H2 CH4
  • 7. Straight-Chain Alkanes: • Contain any number of carbon atoms, one after the other, in a chain • They always end in –ane • To draw the structural formula for a straight-chain alkane, write the symbol for carbon as many times as necessary to get the proper chain length. • Then, fill in with hydrogens and lines representing covalent bonds. – Each covalent bond is equivalent to two electrons.
  • 9. Homologous Series: The straight chain of alkanes are an example of a homologous series. A group of compounds form a homologous series if there is a constant increase/increment of change in molecular structure from one compound in the series to the next. The -CH2- group is the increment of change in straight –chain alkanes. As the number of carbons in the straight-chain alkane increases, so does the boiling point and their melting point.
  • 10. • Molecular Formula: • CH4 Methane • Complete Structural Formulas: • Show all the atoms and bonds in a molecule. Complete Structural Formula • Condensed Structural Formulas: • Leave out some bonds and/or atoms from the structural formula. Although they do not appear, you must understand that these bonds and atoms are Condensed Structural Formula there.
  • 11. Nomenclature/ Naming System:  IUPAC: International Union of Pure and Applied Chemistry. All the names end in –ane. The root part of an alkane´s name indicates how many carbon atoms it contains. Scientists also rely on a combination of systematic, semisystematic, and common names to identify organic compounds.  Some organic compounds are best known for their common names.
  • 13. Branched-Chain Alkanes • An alkane with one or more alkyl groups – An alkyl group is a hydrocarbon substituent • Substituent: an atom or group of atoms that can take the place of a hydrogen atom on a parent hydrocarbon molecule. – An alkyl group consists on an alkane with one hydrogen removed. – Sometimes referred to as radicals. – Change the suffix –ane from the parent structure to -yl
  • 14. Rules for Naming Branched-Chain Alkanes: 1. Find the longest chain of carbons in the molecule. We consider this the parent structure. 2. Number the carbons in the main chain sequence. Start at the end that will give the groups attached to the chain the smallest numbers. 3. Add numbers to the names of the substituent groups to identify their positions on the chain. These numbers become prefixes to the name of the parent alkane. 4. Use prefixes to indicate the appearance of a group more than once in the structure. Ex. Di-, tri-, tetra-; penta-, etc. 5. List the names of the alkyl substituents in alphabetical order. 6. Use proper punctuation. Commas( ,) are used to separate numbers, hyphens(-) are used to separate numbers and words. The entire name is written without spaces.
  • 16. To draw the formula when given the name: • With an alkane name and knowledge of the IUPAC rules, it is easy to reconstruct the structural formula. • Steps: 1. Find the root word(ending in –ane) in the hydrocarbon name. 2. Number the carbons on this parent chain. 3. Identify the substituent groups. Attach the substituents to the numbered parent chain at the proper positions. 4. Add hydrogens as needed.
  • 18. Other Properties of Alkanes: -They are non-polar -Hydrocarbons of low molar mass tend to be gases or low-boiling liquids. -Non-polar organic molecules are insoluble in water. -Rule: “Like dissolves like” -Polar dissolves polar and non-polar dissolves non-polar. - Non-polar will never mix with a polar.
  • 19. Practice Problems: Name the following compounds
  • 20.
  • 21. Unsaturated Hydrocarbons: Objectives: • Explain the difference between unsaturated and saturated hydrocarbons. • Differentiate between the structures of alkenes and alkynes.
  • 22. Alkenes • Alkanes are said to be saturated compounds because they contain a maximum number of hydrogens. • Alkenes and alkynes, on the other hand, contain double and triple bonds respectively. • They are said to be unsaturated compounds because they contain fewer number of hydrogens in their structure.
  • 23. IUPAC Naming System for Alkenes: 1. Find the longest chain in the molecule that contains the double bond. This is the parent alkene. As a base, you use the base name of alkanes and change the suffix –ane to –ene. 2. The chain is numbered in the same way that alkanes, except that the carbon atoms of the double bond get the lowest possible numbers. 3. Substituents on the chain are named and numbered in the same way they are for alkanes. Ethene and propene are the simplest alkenes.
  • 24. Ethene 3D Ethene 2D: Propene 2D Propene 3D
  • 25. Name the following alkenes:
  • 26. Alkynes: • Are hydrocarbons containing carbon- carbon triple covalent bonds • They are unsaturated compounds • They are not plentiful in nature • The simplest alkynes are: ethyne, propyne, butyn e • Ethyne is commonly called acetylene.
  • 27.
  • 28. Name the following compound: