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    # of Carbons Name Formula (C: AP Chemistry Chapter 22 - Organic Chemistry

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    Chemist Mohamed Mohy
    This document provides an overview of organic chemistry concepts including: 1) Alkanes which are saturated hydrocarbons whose structure and properties are determined by their molecular formula. Common reactions include combustion, substitution, and dehydrogenation. 2) Alkenes and alkynes which contain double and triple carbon bonds respectively and can undergo addition and geometric isomerism. 3) Aromatic hydrocarbons such as benzene which have delocalized pi electrons and can form ortho, meta, and para substitution isomers. 4) The petrochemical industry which produces gasoline and other fractions through cracking long chain petroleum molecules.

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    # of Carbons Name Formula (C: AP Chemistry Chapter 22 - Organic Chemistry

    Uploaded by

    Chemist Mohamed Mohy
    41 views5 pages
    This document provides an overview of organic chemistry concepts including: 1) Alkanes which are saturated hydrocarbons whose structure and properties are determined by their molecular formula. Common reactions include combustion, substitution, and dehydrogenation. 2) Alkenes and alkynes which contain double and triple carbon bonds respectively and can undergo addition and geometric isomerism. 3) Aromatic hydrocarbons such as benzene which have delocalized pi electrons and can form ortho, meta, and para substitution isomers. 4) The petrochemical industry which produces gasoline and other fractions through cracking long chain petroleum molecules.

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    Chap 22 Notes

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    This document provides an overview of organic chemistry concepts including: 1) Alkanes which are saturated hydrocarbons whose structure and properties are determined by their molecular formula. Common reactions include combustion, substitution, and dehydrogenation. 2) Alkenes and alkynes which contain double and triple carbon bonds respectively and can undergo addition and geometric isomerism. 3) Aromatic hydrocarbons such as benzene which have delocalized pi electrons and can form ortho, meta, and para substitution isomers. 4) The petrochemical industry which produces gasoline and other fractions through cracking long chain petroleum molecules.

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    © All Rights Reserved
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    41 views5 pages

    # of Carbons Name Formula (C: AP Chemistry Chapter 22 - Organic Chemistry

    Uploaded by

    Chemist Mohamed Mohy
    This document provides an overview of organic chemistry concepts including: 1) Alkanes which are saturated hydrocarbons whose structure and properties are determined by their molecular formula. Common reactions include combustion, substitution, and dehydrogenation. 2) Alkenes and alkynes which contain double and triple carbon bonds respectively and can undergo addition and geometric isomerism. 3) Aromatic hydrocarbons such as benzene which have delocalized pi electrons and can form ortho, meta, and para substitution isomers. 4) The petrochemical industry which produces gasoline and other fractions through cracking long chain petroleum molecules.

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    of 5

    AP Chemistry Chapter 22 - Organic Chemistry

    22.1 Alkanes: Saturated Hydrocarbons


    A. Straight-chain Hydrocarbons
    1. Straight-chain alkanes have the formula C nH2n+2
    2. Carbons are sp3 hybridized

    The First 10 Alkanes


    # of Carbons Name Formula (C nH2n+2)
    1 Methane CH4
    2 Ethane C2H6
    3 Propane C3H8
    4 Butane C4H10
    5 Pentane C5H12
    6 Hexane C6H14
    7 Heptane C7H16
    8 Octane C8H18
    9 Nonane C9H20
    10 Decane C10H22
    B. Structural Isomers
    1. Same formula, but the atoms are bonded together in a different order
    2. Different bonding order results in different properties

    C4H10 Butane C4H10 2-methylpropane

    C. Rules for Naming Alkanes (Nomenclature)


    1. For a branched hydrocarbon, the longest continuous chain of carbon atoms
    gives the root name for the hydrocarbon
    2. When alkane groups appear as substituents, they are named by dropping
    the -ane and adding -yl.
    3. The positions of substituent groups are specified by numbering the longest
    chain of carbon atoms sequentially, starting at the end closest to the
    branching.
    4. The location and name of each substituent are followed by the root alkane
    name. The substituents are listed in alphabetical order (irrespective of any
    prefix), and the prefixes di-, tri-, etc. are used to indicate multiple identical
    substituents.

    1
    D. Reactions of Alkanes
    1. Combustion reactions
    a. 2C2H6(g) + 7O2(g) à 4CO2(g) + 6H2O(g)
    2. Substitution reactions
    a. CH 4 + Cl2 →
    hv
    CH 3 Cl + HCl
    methane chloromethane

    3. Dehydrogenation reactions
    a. CH 3 CH 3 Cr
    2O  → CH 2 = CH 2 + H 2
    3 at 500° C

    ethane ethylene

    E. Cyclic Alkanes (Cycloalkanes)


    1. Alkanes in which the carbon atoms are arranged in a ring, or cyclic,
    structures

    a. The 90° angle in cyclobutane is not nearly tetrahedral, therefore the


    molecule is quite unstable
    2. Nomenclature
    a. Rings are numbered to give the smallest substituent numbers
    possible
    b. Largest substituents are given the lowest possible numbers

    22.2 Alkenes and Alkynes


    A. Alkenes
    1. Hydrocarbons that contain double bonds
    a. The simplest alkene is ethene, or ethylene
    (C 2H4)
    b. Alkenes are nonpolar molecules
    B. Geometric Isomers
    1. Isomers in which the order of atom bonding is the
    same but the arrangement of atoms in space is
    different
    2. A molecule can have a geometric isomer only if two carbon atoms in a rigid
    structure each have two different groups attached

    Cis 1,2-dichloroethane Trans 1,2-dichloroethane

    2
    3. In some isomer pairs, one isomer is biologically active, while the other is not
    (specificity of enzymes is the cause)
    C. Alkynes
    1. Hydrocarbons with triple covalent bonds
    a. The simplest alkyne is ethyne, or acetylene (C 2H2)

    b. Alkynes are nonpolar molecules


    D. Reactions of Alkenes and Alkynes
    1. Addition reactions
    a. Hydrogenation
    CH 2 = CHCH 3 + H 2 Catalyst
     → CH 3 CH 2 CH 3
    Propene Propane
    b. Halogenation
    CH 2 = CHCH 2 CH 2 CH 3 + Br2 → CH 2 BrCHBrCH 2 CH 2 CH3
    1-Pentene 1-2-dibromopentene
    c. Polymerization
    (1) small molecules are joined together to form a large molecule

    22.3 Aromatic Hydrocarbons


    A. Structure of Aromatics
    1. Hydrocarbons with six-membered carbon rings and delocalized electrons
    a. The simplest aromatic hydrocarbon is benzene (C 6H6)

    b. Aromatic hydrocarbons are nonpolar molecules


    B. Geometric Isomerism
    1. ortho (o-) = two adjacent substituents
    2. meta (m-) = one carbon between substituents
    3. para (p-) = two carbons between substituents

    o-dichlorobenzene m-dichlorobenzene p-dichlorobenzene

    3
    C. Reactions of Aromatic Hydrocarbons
    1. Substitution reactions

    22.4 The Petrochemical Industry


    A Brief Narrative:
    Petroleum contains molecules that vary from short chain (1 to 4 carbons) to very long
    chains (greater than 25 carbons). In the nineteenth century, kerosene and gas oil were
    the most desirable "fraction" of petroleum. With the advent of the internal combustion
    engine, the shorter chain molecules that make up gasoline became more important.
    Until that time they were considered a waste product of the purification of kerosene.

    Rather than waste the kerosene-gas oil fraction, refineries take the long chain
    molecules and break them into the smaller molecules of gasoline in a process called
    "cracking".

    22.5 Hydrocarbon Derivatives


    Classes of Organic Compounds
    Class Functional Group General Formula
    Alcohol
    hydroxyl group (-OH)
    Alkyl halide
    Ether

    Aldehyde

    carbonyl group
    Ketone

    carbonyl group
    Carboxylic acid

    carboxyl group

    4
    Ester

    Amine

    amine group

    Examples:

    Class: Ether Name: dimethylether

    Class: Ether Name: diethylether

    Class: Carboxylic acid Name: ethanoic acid

    Class : Alcohol Name: ethanol (ethyl alcholol)

    Class: Aldehyde Name: methanaldehyde

    Class: Carboxylic acid Name: propanoic acid

    Class: Ether Name: ethylmethylether

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