Scribd Logo
Upload

Welcome to Scribd!

    • 104 views

    Essential Organic Chemistry: Isomers and Stereochemistry

    Uploaded by

    Paulina Mendoza B.
    The document summarizes different types of isomers including constitutional isomers, cis-trans isomers, chiral molecules, enantiomers, and how to determine the R/S configuration using CIP priorities. It discusses concepts like asymmetric centers, how enantiomers are mirror images that cannot be superimposed, and examples of determining the R/S configuration of different chiral molecules.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd

    Essential Organic Chemistry: Isomers and Stereochemistry

    Uploaded by

    Paulina Mendoza B.
    104 views38 pages
    The document summarizes different types of isomers including constitutional isomers, cis-trans isomers, chiral molecules, enantiomers, and how to determine the R/S configuration using CIP priorities. It discusses concepts like asymmetric centers, how enantiomers are mirror images that cannot be superimposed, and examples of determining the R/S configuration of different chiral molecules.

    Original Title

    Ch 8 Yurkanis Isomeros y Estereoquimica

    Copyright

    © © All Rights Reserved

    Available Formats

    PPT, PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    The document summarizes different types of isomers including constitutional isomers, cis-trans isomers, chiral molecules, enantiomers, and how to determine the R/S configuration using CIP priorities. It discusses concepts like asymmetric centers, how enantiomers are mirror images that cannot be superimposed, and examples of determining the R/S configuration of different chiral molecules.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    104 views38 pages

    Essential Organic Chemistry: Isomers and Stereochemistry

    Uploaded by

    Paulina Mendoza B.
    The document summarizes different types of isomers including constitutional isomers, cis-trans isomers, chiral molecules, enantiomers, and how to determine the R/S configuration using CIP priorities. It discusses concepts like asymmetric centers, how enantiomers are mirror images that cannot be superimposed, and examples of determining the R/S configuration of different chiral molecules.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 38

    Essential Organic Chemistry

    Paula Yurkanis Bruice

    Chapter 8

    Isomers and Stereochemistry

    William Setzer, Bernhard Vogler, Mary Setzer


    University of Alabama - Huntsville
    Review of Isomerism
     Isomers – Different compounds that have
    the same molecular formula.
     Constitutional Isomers – differ because
    their atoms are connected in a different
    order.
    CH3CH2-O-CH2CH3 vs. CH3CH2CH2CH2OH
    Constitutional Isomers
    8.1 Cis-Trans Isomers
     Differ in the arrangement of their atoms in
    space (cannot interconvert)- Alkenes.
    8.1 Cis-Trans Isomers
     Cyclic structure.
    8.2 Chirality
     Chiral –
    Nonsuperimposable on its
    mirror image.
     Achiral – Superimposable
    on its mirror image.
     If a molecule (or object) has
    a mirror plane or an
    inversion center, it cannot be
    chiral.
    Chiral or Achiral?
     cis-1,3-dimethylcyclopentane

    achiral

    mirror plane
    Chiral or Achiral?
     trans-1,3-dimethylcyclopentane

    chiral
    Chiral or Achiral?
     1,1-dimethylcyclohexane

    achiral
    8.3 Asymmetric Centers

     An asymmetric center is an atom that


    is bonded to four different groups.
    Chiral or Achiral?
    Asymmetric
     2-butanol center

    chiral mirror image


    Chiral or Achiral?
     2-bromopropane

    achiral
    8.4 Isomers with One Asymmetric Center
    8.4 Isomers with One Asymmetric Center
    Enantiomers
     A chiral compound and its mirror image are
    called enantiomers.
     2-butanol:

    enantiomers
    Enantiomers
     Asparagine: mirror
    plane
    O OH HO O
    C C

    H2N C H H C NH2

    CH2 CH2
    C C
    H2N O O NH2
    L-asparagine D-asparagine
    (from asparagus) (from vetch)
    bitter taste sweet taste
    enantiomers
    8.5 Drawing Enantiomers
    8.6 Naming Enantiomers: The R,S System
    Absolute Configuration
     R and S
    • Look down the bond from the chiral carbon to
    the smallest group:

    CH 2CH3 1 2
    OH HO CH2CH3
    H C = C
    CH3 CH3
    3
    Absolute Configuration
     R and S
    • Look down the bond from the chiral carbon to
    the smallest group:

    CH 2CH3 1 2
    OH HO CH2CH3
    H C = C
    CH3 CH3
    3
    Absolute Configuration
     R and S
    • Assign priorities to the remaining groups based
    on atomic numbers.
    • Clockwise (highest to lowest priority)  R
    • Counterclockwise  S
    CH 2CH3 1 2
    OH HO CH2CH3
    H C = C
    CH3 CH3
    3
    Absolute Configuration
     R and S
    • Assign priorities to the remaining groups based
    on atomic numbers.
    • Clockwise (highest to lowest priority)  R
    • Counterclockwise  S
    CH 2CH3 1 2
    OH HO CH2CH3
    H C = C
    CH3 CH3
    3
    (R)-2-butanol
    Absolute Configuration
     Assign priority:
    • Atomic number of atom directly bonded.
    • If the same atom is bonded, go to the next atom,
    etc.
    • Groups containing multiple bonds are treated as
    though multiple atoms were attached:
    N C
    C O = C O C N = C N
    O C N C
    Absolute Configuration
     Determine the absolute configuration of the
    following compounds:
    3 1
    H3C 4 F 4
    H H
    C C
    Cl CH
    Br S 2 D R 2 3
    1 3

    2 O
    (CH3)2CHCH2 4
    1
    H
    H C 4
    C H

    S Cl C
    CH3CH2CH2CH2 1 C N
    3 CH3CH2 R 2
    3
    Absolute Configuration
     Determine the absolute configuration of the
    following compounds:
    CH3 CH3
    1 2
    CH3O CH 4 CH3O CH 4
    H H
    C C
    2
    S CH3 1
    R CH3
    CH3CH2 CH 3 CH3CH2 CH 3

    OH OCH3
    1 2
    CH2=CH 4 CH2=CH 4
    H H
    C C
    2
    S CH3 S C CH
    CH3CH2 3 (CH3)2CH 1
    3

    You might also like