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Carbon: Not Just Another Element

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Title: Carbon: Not Just Another Element


1
Carbon Not Just Another Element
  • Chapter 23

2
Learning Objectives
  • Students understand
  • General principles of structure and bonding
    applied to organic compounds
  • Why carbon forms a vast array of diverse chemical
    compounds
  • Students will be able to
  • Classify organic compounds based on formula and
    structure
  • Recognize and draw structures of structural
    isomers and stereoisomers for carbon compounds
  • Draw structures of molecules, given the name
    and/or the formula, and name organic compounds
    using standard nomenclature rules

3
23.1 Why Carbon?
  • Organic compounds contain the element carbon,
    which can bond with other carbon atoms to form
    straight chains and branched chains.
  • Isomers
  • identical composition but linked in different ways

4
23.2 Hydrocarbons
  • Carbon and hydrogen only
  • Alkanes, cycloalkanes
  • Alkenes
  • Alkynes
  • Aromatic compounds

5
Alkanes
  • Alkanes contain only single bonds between carbon
    atoms.
  • Alkanes and other organic compounds are best
    represented by structural formulas and can be
    named using systematic rules determined by the
    International Union of Pure and Applied Chemistry
    (IUPAC).

6
Alkanes
  • Each alkane has the general formula CnH2n2 n is
    the number of carbon atoms.
  • Straight-chain hydrocarbons, also called
    unbranched or normal, all carbon atoms are
    connected in a long chain.
  • The name of each alkane ends in the suffix -ane.

7
Alkanes
  • The root of the name corresponds to the longest
    carbon chain in the compound
  • Substituent groups are identified by a name and
    position in the carbon chain
  • called alkyl group
  • 2 or more of the same alkyl group (use
    di-,tri-tetra-) otherwise list in alphabetical

8
Name Formula Name Formula
Methane CH4 Hexane C6H14
Ethane C2H6 Heptane C7H16
Propane C3H8 Octane C8H18
Butane C4H10 Nonane C9H20
Pentane C5H12 Decane C10H22
9
Saturated Compounds
  • Saturated hydrocarbons have all carbon-carbon
    single bonds.
  • Unsaturated hydrocarbons contain carbon-carbon
    multiple bonds.

10
Cyclic Alkanes and Alkane Properties
  • Alkanes that contain hydrocarbon rings are called
    cyclic alkanes.
  • Alkanes are nonpolar compounds that have low
    reactivity and lower melting points and boiling
    points (weak C-C bonds strained hydrocarbons)
    than polar molecules of similar size and mass.

11
Alkenes and Alkynes
  • Alkenes and alkynes are hydrocarbons that contain
    at least one double or triple bond, respectively.
  • Alkenes and alkynes are nonpolar compounds with
    greater reactivity than alkanes but with other
    properties similar to alkanes.

12
Alkenes and Alkynes
  • Alkenes and alkynes can also be named using IUPAC
    rules.
  • Look at the longest chain to figure out the
    parent name.
  • Alkenes have the general formula of CnH2n.
  • Root ending is -ene
  • Alkynes have the general formula of CnH2n-2.
  • Root ending is -yne

13
Naming Isomers
  • Look at the longest continuous chain that
    determines the root name. This is the last part
    of the name.
  • Next name the alkyl group that substitutes on the
    parent chain.
  • Specify the location of the groups by numbering
    longest chain sequentially.
  • hexane vs. 2-methylpentane vs. 2,3
    dimethylbutane vs. 2,2 - dimethylbutane

14
Naming Isomers
  • Alkenes exhibit cis-trans isomerism because
    rotation around the double bond is restricted.
  • In cis isomerism the heavier groups are on the
    same side of the double bond.
  • In trans isomerism the heavier groups are on
    opposite sides of the double bond.

15
  • cis 2-pentene
  • trans-2-pentene

16
Aromatic Hydrocarbons and Petroleum
  • Aromatic hydrocarbons contain benzene rings as
    part of their molecular structures. Nonaromatic
    hydrocarbons are called aliphatic hydrocarbons.
  • Extra stability due to resonance stabilization

17
Aromatic Hydrocarbons
  • May contain two or more benzene rings fused
    together
  • Some are carcinogenic
  • Major sources are petroleum and natural gas
  • Fractional distillation can separate petroleum
    into components

18
23.3-23.4 Functional Groups
  • Halide
  • Alcohol R-OH
  • Ether R-O-R
  • Aldehyde R-(CO)-H
  • Ketone R-(CO)-R
  • Carboxylic acid R-(CO)-OH
  • Ester R-(CO)-O-R
  • Amide R-NH2, R-NHR, R-NRR
  • Amine H-NH2, H-NHR, H-NRR
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