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    This document discusses stereochemistry and isomers. It defines stereochemistry as the study of the three-dimensional structure of molecules. There are two classes of isomers - constitutional isomers which have the same molecular formula but different connectivity, and stereoisomers which have the same connectivity but differ in atomic arrangement. Stereoisomers include geometrical isomers, optical isomers, and conformational isomers. Constitutional isomers can differ in their carbon skeleton (chain isomers), position of functional groups (position isomers), type of functional group (functional isomers), or substituents on functional groups (metameric isomers). Compounds can also exist in equilibrium as tautomers through hydrogen migration. Factors like conjugation

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    This document discusses stereochemistry and isomers. It defines stereochemistry as the study of the three-dimensional structure of molecules. There are two classes of isomers - constitutional isomers which have the same molecular formula but different connectivity, and stereoisomers which have the same connectivity but differ in atomic arrangement. Stereoisomers include geometrical isomers, optical isomers, and conformational isomers. Constitutional isomers can differ in their carbon skeleton (chain isomers), position of functional groups (position isomers), type of functional group (functional isomers), or substituents on functional groups (metameric isomers). Compounds can also exist in equilibrium as tautomers through hydrogen migration. Factors like conjugation

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    2 views17 pages

    Stero 1

    Uploaded by

    htata.11.ain
    This document discusses stereochemistry and isomers. It defines stereochemistry as the study of the three-dimensional structure of molecules. There are two classes of isomers - constitutional isomers which have the same molecular formula but different connectivity, and stereoisomers which have the same connectivity but differ in atomic arrangement. Stereoisomers include geometrical isomers, optical isomers, and conformational isomers. Constitutional isomers can differ in their carbon skeleton (chain isomers), position of functional groups (position isomers), type of functional group (functional isomers), or substituents on functional groups (metameric isomers). Compounds can also exist in equilibrium as tautomers through hydrogen migration. Factors like conjugation

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    of 17

    Stereochemistry

    Prepared by
    Dr. Kurls Ekram Anwer

    Dr. Kurls Ekram 1


    Dr. Kurls Ekram 2
    Stereochemistry:
    is the sciences that study three-dimensional structure of a molecule.

    Dr. Kurls Ekram 3


    The Two Major Classes of Isomers
    Isomerism : Compounds with the same molecular formula but different structures.
    For Ex: C2H6O → CH3CH2OH or CH3OCH3
    There are two types of isomers

    Constitutional isomers Stereoisomers


    Compounds have the same Isomers that have the same
    molecular formula but have connectivity but differ in the
    different structure (connectivity). arrangement of their atoms in space.
    For Ex: C2H6O CH3CH2OH Or CH3OCH3

    1) Chain (skeletal) isomers Geometrical isomers Optical isomers


    2) Position isomers Or
    3) Functional isomers
    4) Metameric isomers Conformational Configurational
    5) Tautomerism isomers isomers
    Dr. Kurls Ekram 4
    Constitutional isomers properties
    For Ex: C2H6O CH3CH2OH Or CH3OCH3

    ❖ different Commane and IUPAC names.

    ❖ different physical properties, so they are separable by physical


    techniques such as distillation. different in boiling point

    ❖ different chemical properties. They behave differently or give different


    products in chemical reactions.

    Dr. Kurls Ekram 5


    1) Chain isomers (Skeletal isomers):
    compounds different in their carbon skeleton.

    Ex1 : C4H10

    Ex2: C5H12

    Q: draw all constitutional isomers for formula C6H12.

    Dr. Kurls Ekram 6


    2) Positional isomers:
    compounds differ in the position of the functional group (Position of bonds).

    Ex1: C3H7Br

    Ex2: C3H9N

    Ex3: C4H9OH

    Dr. Kurls Ekram 7


    Ex4: C6H8O2

    Ex5: C7H7Cl

    Dr. Kurls Ekram 8


    3) Functional group isomerism
    compounds differ in the type of their functional group.

    Ex1: C3H6O

    EX2: C2H6O

    Q: Draw all Constitutional isomers for formula C3H6O , C3H6O2.

    Dr. Kurls Ekram 9


    4) Metamorism (Metameric isomerism)
    compounds have the same functional group but differ in the kind of substituent on its sides.

    Ex1: Ethers with MF C4H10O.

    Ex1: ketone with MF C5H10O.

    Dr. Kurls Ekram 10


    5) Tautomerism (tautomers)
    Compound occurs as a mixture of 2 function groups isomer, in equilibrium with
    each other as a result of reversible migration of a hydrogen atom.
    Types of Tautomerism
    A) Daid tautomerism (Died system)
    1,2 Hydrogen migrates between 2 adjacent atoms

    B) Triad tautomerism (Tried system)

    1,3 migration

    Dr. Kurls Ekram 11


    Factors which increase % of enol form than 1:%
    ❖ Conjugation
    ❖ Intramolecular H-B
    ❖ Increase acidity of alpha –hydrogen

    Ex1: Acetylacetone , 1,3-cyclohexandione

    This hydrogen is Stabilizied by


    more acidic so • Formation of hydrogen bond
    increase the percent • Formation of six-membered ring
    of enol form • Resonance conjugated system

    Dr. Kurls Ekram 12


    Ex2: Ethyl acetoacetate

    The lone pair on oxygen decrease the acidity (decrease the acidity of hydrogen CH2) so decrease
    the enol form

    Ex3: 1,3-cyclohexandione

    Dr. Kurls Ekram 13


    Thank you

    14
    Dr. Kurls Ekram 14
    Homework

    Dr. Kurls Ekram 15


    2

    Dr. Kurls Ekram 16


    3

    Dr. Kurls Ekram 17

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