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    Nomenclatures: Determining R/S Nomenclature at A Glance in Three Easy Steps

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    YekitaS
    1. The document discusses nomenclature rules for determining R/S stereochemistry and E/Z stereochemistry of alkenes. 2. For R/S nomenclature, it describes a 3-step method using the "drive-the-car" analogy to assign stereochemistry based on the priority of groups and whether they are clockwise or counterclockwise around a steering wheel. 3. For E/Z nomenclature of alkenes, it explains that Cahn-Ingold-Prelog priority rules are used to assign configurations based on whether the two highest priority groups are on the same (Z) or opposite (E) sides of the double bond.

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    Nomenclatures: Determining R/S Nomenclature at A Glance in Three Easy Steps

    Uploaded by

    YekitaS
    17 views3 pages
    1. The document discusses nomenclature rules for determining R/S stereochemistry and E/Z stereochemistry of alkenes. 2. For R/S nomenclature, it describes a 3-step method using the "drive-the-car" analogy to assign stereochemistry based on the priority of groups and whether they are clockwise or counterclockwise around a steering wheel. 3. For E/Z nomenclature of alkenes, it explains that Cahn-Ingold-Prelog priority rules are used to assign configurations based on whether the two highest priority groups are on the same (Z) or opposite (E) sides of the double bond.

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    Nomenclatures

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    1. The document discusses nomenclature rules for determining R/S stereochemistry and E/Z stereochemistry of alkenes. 2. For R/S nomenclature, it describes a 3-step method using the "drive-the-car" analogy to assign stereochemistry based on the priority of groups and whether they are clockwise or counterclockwise around a steering wheel. 3. For E/Z nomenclature of alkenes, it explains that Cahn-Ingold-Prelog priority rules are used to assign configurations based on whether the two highest priority groups are on the same (Z) or opposite (E) sides of the double bond.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    17 views3 pages

    Nomenclatures: Determining R/S Nomenclature at A Glance in Three Easy Steps

    Uploaded by

    YekitaS
    1. The document discusses nomenclature rules for determining R/S stereochemistry and E/Z stereochemistry of alkenes. 2. For R/S nomenclature, it describes a 3-step method using the "drive-the-car" analogy to assign stereochemistry based on the priority of groups and whether they are clockwise or counterclockwise around a steering wheel. 3. For E/Z nomenclature of alkenes, it explains that Cahn-Ingold-Prelog priority rules are used to assign configurations based on whether the two highest priority groups are on the same (Z) or opposite (E) sides of the double bond.

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    NOMENCLATURES

    Determining R/S Nomenclature at a Glance in Three Easy Steps Note: With this method you never have to switch groups to see what the stereochemistry is. Using the "drive-the-car" analogy, what we are doing here is defining the steering wheel in relation to the steering column (which is normally behind the steering wheel):

    1. Determine the priorities of the four attached groups from highest (1) to lowest (4). This is the same as in all methods. 2. Draw the steering wheel. Draw a curved arrow around from 1 to 2 to 3 and back to 1 and note which direction this arrow goes, clockwise (cw) or counterclockwise (ccw). The distinct feature of this method is that you make a full circle, from 1 to 2 to 3 to 1, completely ignoring the lowest priority group. 3a. If the lowest priority group is behind the steering wheel, then this is the standard orientation: clockwise is R and counter-clockwise is S. (Turning the steering wheel clockwise turns the car to the right--R.) Note that Fischer projections are best depicted as bow ties with horizontal groups coming out and vertical groups going back from the central carbon atom. 3b. If the lowest priority group is in front of this curved arrow, then the assignment is reversed: clockwise is S and counterclockwise is R. (Basically, you are looking at the steering wheel from the perspective of the engine compartment!)

    E- and Z-nomenclature of alkenes


    On the previous pages, we looked at naming alkenes as cis- and trans-. It is important to note that the two methods are different (i.e. they are based on different rules) and they are NOT interchangeable, see below for an example. The cis- / trans- style is based on the longest chain whereas the E/Z style is based on a set of priority rules. You need to know both styles.

    cis-but-2-ene or (Z)-but-2-ene

    cis-2-chlorobut-2-ene or (E)-2-chlorobut-2-ene

    The E- and Z- style is more reliable and particularly suited to highly substituted alkenes, especially when the substituents are not alkyl groups. The Cahn-Ingold-Prelog priority rules are used for naming geometric isomers (e.g. E- or Z-alkenes) and other stereoisomers (see later). These rules are based on atomic number, and the first point of difference.

    Imagine each alkene as two pieces, each piece containing one of the sp 2 C Assign the priority (high = 1, low = 2) to each atom on each sp2 C based on atomic number Determine the relative position of the two higher priority groups If they are on the same side then it is a (Z)-alkene (German; zusammen = together) If they are on opposite sides then it is an (E)-alkene (German; entgegen = opposite)

    If there is more than one C=C that can be E/Z, then the location needs to be included with the locant, e.g. (2E,4Z)-

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