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Organic chemistry. Organic Compounds. Organic Compounds - any covalently bonded compound containing carbon except carbonates CO 3 - , carbon monoxide CO, carbon dioxide CO 2 and acetates C 2 H 3 O 2 -. A. Organic Nomenclature. General Characteristics of Organic Molecules.

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Organic compounds
Organic Compounds

  • Organic Compounds - any covalently bonded compound containing carbon

  • except carbonates CO3-, carbon monoxide CO, carbon dioxide CO2 andacetates C2H3O2-



General characteristics of organic molecules
General Characteristics of Organic Molecules

  • Carbon always forms 4 covalent bonds

  • due to its hybridization of its s and p

  • orbitals



  • Stabilities of organic molecules
    Stabilities of Organic Molecules

    • Carbon forms very strong bonds between H, O, N, and halogens.

    • Carbon also forms strong bonds with itself.

    • Therefore, C can form stable long chain or ring

  • structures.

    • Bond strength increases from single to double to

      • triple bond.

    • Bond length decreases in the same direction.


    Hydrocarbons
    Hydrocarbons

    • Hydrocarbons- Organic compounds that contain only carbon & hydrogen

    • Alkanes- contain only single covalent bonds

    • Alkenes- contain one or more carbon - carbon

    • double bond

    • Alkynes- contain one or more carbon-carbon triple

    • bond


    Saturated unsaturated hydrocarbons
    Saturated & Unsaturated Hydrocarbons

    • Saturated hydrocarbons – contain only single carbon-carbon bonds (alkanes)

    • Unsaturated hydrocarbons – contain double

    • carbon-carbon bonds (alkenes)

    • or triple carbon-carbon (alkynes) bonds


    Formulas
    Formulas

    • Alkanes = CnH2n+2

    • Alkenes = CnH2n

    • Alkynes = CnH2n-2


    Nomenclature
    Nomenclature

    • Must memorize prefixes

    • To name, look at the formula for the hydrocarbon

    • Determine if it is an alkane, alkene, or alkyne

    • Use the prefix for the number of carbons

    • Add ending (ane, ene, yne)


    Structural formulas
    Structural Formulas

    • “Lazy” way to write the Hydrogens

    • Instead of drawing the bonds, just state how many hydrogens are attached

    • NOTE: The bonds are between CARBONS in a parent chain, and not hydrogens!

    Structural Formula

    Lewis Structure


    • B. the first ten alkanes

    • CH4 - methane

    • C2H6 - ethane

    • C3H8 - propane

    • C4Hl0 - butane

    • C5H12- pentane


    • C6H14 - hexane

    • C7H16 - heptane

    • C8H18 - octane

  • C9H20 - nonane

  • C10H22 - decane


    C. the general formula is CnH 2n +2

    1. where n stands for the number of carbons

    D. Branched chain saturated hydrocarbons

    1. must name the longest straight chain

    2. number the straight chain so the branches

    have the lowest number


    3 list the branches in alphabetical order

    e.g. 3-ethyl 2 methyl hexane


    e.g. 3-ethyl 2 methyl hexane

    Draw back bone for compound = in this case it is hexane

    C

    C-C-C-C-C-C

    1

    2

    3

    4

    5

    6

    C

    C

    Number the carbons

    Attach branch group

    Make sure all C have 4 bonds


    Designate the location
    Designate the Location

    Designate the location (number of the carbon on

    the parent chain) for each attached group

    2-methyl

    1 2 3 4 5

    2 - methyl pentane


    Some simple alkanes
    Some Simple Alkanes

    2-methylpentane

    • 2,2-dimethylbutane

    3-ethylhexane

    • 2,3-dimethylbutane



    II. Types of formulas

    Structural formulas - shows the

    structure of a molecule

    B. Condensed structural formulas


  • e.g. cyclohexane


  • Drawing and naming cycloalkanes
    Drawing and Naming Cycloalkanes

    Cycloalkanes are represented by polygons. A triangle represents cyclopropane, a square represents cyclobutane, a pentagon represents cyclopentane, and so on.


    Alkenes and alkynes
    Alkenes and Alkynes

    • Unsaturated

      • contain carbon-carbon double and triple bond to which more hydrogen atoms can be added.

    • Alkenes: carbon-carbon double bonds

    • Alkynes: carbon-carbon triple bonds.


    IV. alkenes - doubled bonded hydrocarbons considered

    to be unsaturated

    a. the double bond is located between two C

    i. ethene

    • H- C = C - H

    • I I

  • H H

  • b. change the ane ending to ene


    c. in very large molecules you must give a number

    where the double bond begins

    e.g. 2- butene

    d. If there are more than one double bond the ene

    is preceded by number of double bonds

    1.3 pentadiene

    V. Alkynes - triple bonded hydrocarbons - also unsaturated

    A. the triple bond is located between the two C

    1. ethyne

    H-C=C-H


    B. change the ane ending to yne

    C. must also indicate where the triple bond starts

    e.g. 2-pentyne


    Naming alkenes and alkynes
    Naming Alkenes and Alkynes

    When the carbon chain has 4 or more C atoms, number the chain to give the lowest number to the double or triple bond.

    1 2 3 4

    CH2=CHCH2CH3 1-butene

    CH3CH=CHCH3 2-butene CH3CCCH3 2-butyne


    Endings
    Endings

    • Alkanes (all C-C single bonded parent chain) end in –ane

      • MethaneCH4

      • EthaneC2H6

      • PropaneC3H8

    • Attached carbon groups (substituents) end in –yl

      • Methyl CH3 -

      • EthylCH3CH2-

      • Propyl CH3CH2CH2 –  

    3-ethylpentane


    VII alkyl halides

    The attachment of a Halogen to a carbon group

    (F, Cl, Br, I)

    Chloro methane

    dicloro, difluoro methane

    2 – bromo butane


    VII. alcohols - contain OH groups

    A. ethanol

    B. change the e to ol

    C. methane to methanol

    VIIIKetones - contains double bonded oxygen

    located anywhere but the end

    A. change to e to one

    B. propane to propanone


    IXaldehydes - contains double bonded oxygen only

    at the end

    A. change e to al

    B. ethane to ethanal

    X carboxylic Acid - contain a double bonded oxygen

    and a hydroxylgroup

    A. change to e to oic acid

    B. ethane to ethanoic acid

    X I ethers

    A. two alkyl groups attached to an oxygen

    B. dimethyl ether


    Aromatic compounds and benzene
    Aromatic Compounds and Benzene

    Aromatic compounds contain benzene.

    Benzene, C6H6 , is represented as a six carbon ring with 3 double bonds.

    Two possible resonance structures can be drawn to show benzene in this form.


    When Benzene rings are attached to groups that have higher priorities – it is

    known as a phenyl group (C6H5-)


    Functional groups
    Functional Groups priorities – it is


    Functional groups1
    Functional Groups priorities – it is


    CO priorities – it is2H

    O

    I

    N

    C

    R

    E

    A

    S

    I

    N

    G

    -CH

    O

    C

    -OH

    C=C

    R-,C6H5-,Cl-, Br-, NO2


    Isomers
    Isomers priorities – it is

    • Straight chain alkanes: An alkane that has all its carbons connected in a row.

    Branched chain alkanes: An alkane that has a

    branching connection of carbons.

    • Isomers:Compounds with same molecular formula

    • but different structures.


    F. structural isomers priorities – it is

    1. same molecular formula put differ in

    structural formula

    2. 4 carbon alkane has two possible isomers

    3. C5H12 has 3 isomers

    4. C6H14 has 5 isomers

    5. C10H22has 75


    • Carbons in butane (C priorities – it is4H10) can be arranged in two ways; four carbons in a row (linear alkane) or a branching (branched alkane). These two structures are two isomers for butane.



    Learning check
    Learning Check have different structures, different physical properties such as melting point and boiling point, and may have different physiological properties.

    • Draw all possible structural isomers of C5H12

    pentane

    2-methlyl butane

    2,2 – dimethyl propane


    Example
    Example have different structures, different physical properties such as melting point and boiling point, and may have different physiological properties.

    • Name C3H8

    • This falls under the equation CnH2n+2

    • Therefore it is an alkane

    • Since n=3 we will use the prefix prop

    • Since it is an alkane we will use the ending ane

    • propane


    Example1
    Example have different structures, different physical properties such as melting point and boiling point, and may have different physiological properties.

    • What is the formula for octene?

    • Since the ending is -ene we know that it is an alkene (CnH2n)

    • Since the prefix is oct we know there are 8 carbons

    • C8H16


    Example2
    Example have different structures, different physical properties such as melting point and boiling point, and may have different physiological properties.

    • Name C5H12

    • 5 carbons = pent

    • CnH2n+2 = alkane (ane)

    • pentane


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