4.3 Naming Bicyclic Compounds

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    RULES FOR NAMING BRIDGED AND FUSED BICYCLIC COMPOUNDS

    1 Name the substituents before the parent chain just as with other alkanes.
    2 Start the name of the parent chain with the bicyclo- prefix.
    3 List the number of carbon atoms between bridgeheads in each path. List these three numbers in brackets from highest to lowest separated by periods.
    To do this:
    Identify the ‘bridgehead carbons.’
    Identify the 3 pathways from one bridgehead carbon to the other and note how many carbon atoms are in between the bridgehead carbon atoms on each path (not including the bridgehead carbons).
    4 End the name of the parent chain with the alkane name that corresponds to all carbon atoms in the ring system including the bridgehead carbon atoms.
    5 Number the parent chain beginning with one of the bridgehead carbons as #1.
    Number through the path between bridgehead carbons with the most carbons 1st.
    Continue through the 2nd bridgehead carbon and number the path with the 2nd most carbons.
    Continue numbering the last remaining path with the fewest carbons.
    Choose the bridgehead carbon to be #1 which results in the first substituent encountered having a lower chain locator. If there is a tie repeat with the next substituent just as with other alkanes.

    Naming Bridged Bicyclic Compounds Practice

    Identify and number the parent chain in each of the following. Then provide the IUPAC name. (These are the examples named in the video lesson.)

    bridged bicyclic compounds 1
    bridged bicyclic compounds 2

    Naming Fused Bicyclic Compounds Practice

    Identify and number the parent chain in each of the following. Then provide the IUPAC name. (These are the examples named in the video lesson.)

    fused bicyclic compounds

    NAMING SPIRO BICYCLIC COMPOUNDS

    1 Name the substituents before the parent chain just as with other alkanes.
    2 Start the name of the parent chain with the spiro- prefix.
    3 List the number of carbon atoms in each ring excepting the spiro carbon. List these two numbers in brackets from lower to higher separated by a period.
    4 End the name of the parent chain with the alkane name that corresponds to all carbon atoms in the ring system including the bridgehead carbon atoms.
    5 Number the parent chain beginning with one of the carbons in the smaller ring adjacent to the spiro-carbon as #1.
    Number through the smaller ring ending with the spiro-carbon.
    Continue numbering through the second ring.
    Choose the carbon of the smaller ring adjacent to the spiro-carbon to be #1 which results in the first substituent encountered having a lower chain locator. If there is a tie repeat with the next substituent just as with other alkanes.

    Naming Spiro Bicyclic Compounds Practice

    Identify and number the parent chain in each of the following. Then provide the IUPAC name. (These are the examples named in the video lesson.)

    bicyclic compound .1
    bicyclic compound .2

    Priority of Organic Functional Groups in Nomenclature

    TABLE OF FUNCTIONAL GROUP PRIORITY FOR NOMENCLATURE
    Functional Group Suffix (Parent Chain) Prefix (Substituent) Example Name
    Carboxylic Acid -oic acid carboxy- ethanoic acid
    Acid Anhydride -oic anhydride alkanoyloxy- ethanoic anhydride
    Ester -oate alkoxycarbonyl- methyl propanoate
    Acyl Halide -oyl halide halocarbonyl- propanoyl chloride
    Amide -amide carbamoyl- ethanamide
    Nitrile -nitrile cyano- propanenitrile
    Aldehyde -al formyl- propanal
    Ketone -one oxo- propan-2-one
    Alcohol -ol hydroxy- propan-2-ol
    Thiol -thiol -mercapto propane-2-thiol
    Amine -amine amino- propan-2-amine
    Alkene -ene N/A but-1-ene
    Alkyne -yne N/A but-1-yne
    Ether N/A alkoxy- 1-methoxypropane
    Sulfide N/A alkylthio- 1-methylthiopropane
    Alkyl Halide N/A halo- 1-chloropropane