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    Chapter 25 The Chemistry of Life: Organic Chemistry

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    Umar

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    Chapter 25 The Chemistry of Life: Organic Chemistry

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    Chapter 25 The Chemistry of Life: Organic Chemistry

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    Umar

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    © All Rights Reserved
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    Chapter 25 The Chemistry of Life: Organic Chemistry

    25.1 Some General Characteristics of Organic Molecules


    Organic chemistry is
    The structures of organic molecules
    The shapes of organic and biochemical molecules are important in determining
    their physical and chemical properties. Consider carbon:

    The stabilities of organic substances

    The stability of organic substances varies – e.g. benzene has special stability due
    to the delocalization of ! electrons.

    Solubility and acid-base properties of organic


    substances

    The prevalence of C-C and C-H bonds results


    in low overall polarity for many organic molecules,
    and such molecules are soluble in nonpolar
    solvents.

    25.2 Introduction to Hydrocarbons


    The simplest class of organic molecules is the hydrocarbons
    25.3 Alkanes
    Single bonds only; “saturated” hydrocarbons (saturated with hydrogen).

    Structures of Alkanes

    VSEPR theory predicts each


    C atom is tetrahedral:
    Structural Isomers

    In straight-chain hydrocarbons the C atoms are joined in a continuous chain.

    Branched-chain hydrocarbons are possible for alkanes with four or more C atoms.
    Structures with different branches can be written for the same formula:

    Structural isomers are compounds with the same molecular formula but different
    bonding arrangements.

    Nomenclature of Alkanes

    Organic compounds are named according to rules established by the International


    Union for Pure and Applied Chemistry (IUPAC).

    prefix base suffix

    To name a compound…

    2. Number the chain from the end


    nearest the first substituent
    encountered

    4. When two or more substituents are


    present, list them in alphabetical order.
    Cycloalkanes

    Carbon can also form ringed structures. 5- and 6-membered rings are most stable:

    Reactions of alkanes

    Rather unreactive due to presence of only C–C and C–H "-bonds.

    25.4 Unsaturated Hydrocarbons


    Alkenes

    Alkenes are unsaturated hydrocarbons that contain C and H atoms and at least
    one C-C double bond.

    Alkenes are named in the same way as alkanes with the suffix -ene replacing the
    -ane in alkanes. The location of the double bond is indicated by a prefix

    Alkenes cannot rotate freely about the double bond (! bond = side-to-side overlap)

    No rotation means
    geometric isomers
    are possible in alkenes

    Structure affects physical properties of alkenes. Cis and trans do not interconvert.
    Alkynes

    Unsaturated hydrocarbons that contain at least one carbon–carbon triple bond.

    Naming is analogous to alkenes

    Addition Reactions of Alkenes and Alkynes

    The dominant reactions for alkenes and alkynes are addition reactions:

    Common additions include H2 (hydrogenation), H2O or hydrogen halides. Alkynes


    are also capable of addition reactions:

    Mechanism of Addition Reactions

    A mechanism is an explanation of how a reaction proceeds.


    Aromatic Hydrocarbons

    Aromatic structures are formally related to


    benzene (C6H6):

    Highly unsaturated: very reactive?

    Even though they contain ! bonds, aromatic


    hydrocarbons undergo substitution reactions
    more readily than addition reactions.

    25.5 Functional Groups: Alcohols and Ethers


    Hydrocarbons are relatively unreactive; for an organic molecule to be reactive it
    needs something additional.

    Alcohols, R–
    R–OH
    Named from parent hydrocarbon; suffix changed to -ol
    The O–H bond is polar and can participate in hydrogen bonding, so alcohols are
    more water soluble than alkanes.

    Ethers, R–
    R–O–R’
    Compounds in which two hydrocarbons are linked by an oxygen are called ethers.

    25.6 Compounds with a Carbonyl Group


    The carbonyl group, C=O, plus the type of atoms attached to the carbonyl carbon
    defines the particular kind of compound.
    Aldehydes and Ketones

    Aldehydes must have at least one H atom attached to the carbonyl C


    Ketones have two carbons bonded to carbonyl carbon

    Carboxylic Acids

    Carboxylic acids contain a carbonyl group with an –OH attached

    Esters

    Esters can be prepared by condensation reactions involving a


    carboxylic acid and an alcohol; the products are the ester and water

    Amines and amides

    Amines are organic bases with general formula R3N.

    Amides are composites of carbonyl and amine functionalities

    25.7 Chirality in Organic Chemistry


    Recall that molecules whose mirror images are nonsuperimposable are chiral.

    Chemists use the labels R– and S– to distinguish between enantiomers.


    Many pharmaceuticals are chiral; often only one enantiomer is clinically active.

    A mixture of two enantiomers in the same quantity is called a racemic mixture.

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