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    Naming Hydrocarbons

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    Rigen Alam
    This document provides information on naming hydrocarbon compounds using IUPAC nomenclature rules. It discusses: - The basic structure and naming of alkanes, alkenes, and alkynes based on carbon number and functional groups - Numbering carbons in compounds with multiple bonds to determine position of substituents - Common prefixes used to indicate carbon chain length - Naming cyclic structures and aromatic compounds like benzene - Applying naming rules to more complex structures involving side chains, functional groups, and multiple bonds

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    © All Rights Reserved
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    Naming Hydrocarbons

    Uploaded by

    Rigen Alam
    219 views28 pages
    This document provides information on naming hydrocarbon compounds using IUPAC nomenclature rules. It discusses: - The basic structure and naming of alkanes, alkenes, and alkynes based on carbon number and functional groups - Numbering carbons in compounds with multiple bonds to determine position of substituents - Common prefixes used to indicate carbon chain length - Naming cyclic structures and aromatic compounds like benzene - Applying naming rules to more complex structures involving side chains, functional groups, and multiple bonds

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    naming-hydrocarbons

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    This document provides information on naming hydrocarbon compounds using IUPAC nomenclature rules. It discusses: - The basic structure and naming of alkanes, alkenes, and alkynes based on carbon number and functional groups - Numbering carbons in compounds with multiple bonds to determine position of substituents - Common prefixes used to indicate carbon chain length - Naming cyclic structures and aromatic compounds like benzene - Applying naming rules to more complex structures involving side chains, functional groups, and multiple bonds

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    219 views28 pages

    Naming Hydrocarbons

    Uploaded by

    Rigen Alam
    This document provides information on naming hydrocarbon compounds using IUPAC nomenclature rules. It discusses: - The basic structure and naming of alkanes, alkenes, and alkynes based on carbon number and functional groups - Numbering carbons in compounds with multiple bonds to determine position of substituents - Common prefixes used to indicate carbon chain length - Naming cyclic structures and aromatic compounds like benzene - Applying naming rules to more complex structures involving side chains, functional groups, and multiple bonds

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 28
    At a glance
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    The key takeaways are that hydrocarbons can be classified into alkanes, alkenes, and alkynes based on their bonding patterns. IUPAC nomenclature provides systematic naming of organic compounds.

    The three classes of hydrocarbons are alkanes (CnH2n+2), alkenes (CnH2n), and alkynes (CnH2n-2).

    Common names were used historically but IUPAC names provide a systematic naming convention. Common names are still used for some simple and familiar compounds.

    Naming Hydrocarbons

    (nomenclature)

    Handout: Hydrocarbons: IUPAC names

    Drawing structures: its all good


    H
    C

    2-butene
    H
    H

    H3C
    H

    H3C CH CH CH3

    C
    H

    CH
    H3C
    H3C

    CH

    CH3

    CH3
    CH3

    This is called the


    condensed structure On a test, choose a method
    that shows all Hs

    CH3CH=CHCH3
    Using brackets can also shorten some formulas:
    CH3(CH2)4CH3 vs. CH3CH2CH2CH2CH2CH3

    Background: formulas for HCs

    Alkanes= CnH2n+2, enes= CnH2n, ynes= CnH2n-2


    Remember enes, then think of what would
    happen if bond was single or triple instead.
    Provides some useful information (e.g. for
    compositional analysis, or to check work)
    Cannot always tell hydrocarbon type based on
    numbers (e.g. propyne vs. propadiene)
    Q - how many hydrogens in each of these:
    6 carbon alkane
    14
    Alkene: C22H
    44
    H3C
    CH3
    8 (2x5 - 2 = 10 - 2)

    Naming: common vs. IUPAC


    Common names used in the 1800s are still
    used for some compounds today:
    O

    H
    C
    H
    OH
    Formic acid

    C
    C
    Acetylene

    C
    H3C
    CH3
    Acetone

    The International Union of Pure and Applied


    Chemistry (IUPAC) was established in 1900s
    Frequent revisions to nomenclature
    Systematic method allows an infinite number of
    compounds to be named given a few rules

    Basic names of hydrocarbons

    Hydrocarbon names are based on: 1) class 2)


    # of C, 3) side chain type and 4) position
    1) name will end in -ane, -ene, or -yne
    2) the number of carbons is given by a Prefix
    1 meth- 2 eth- 3 prop- 4 but- 5 pent6 hex- 7 hept- 8 oct- 9 non- 10 dec Actually, all end in a, but a is dropped when
    next to a vowel. E.g. a 6 C alkene is hexene
    Q - What names would be given to these:
    7C, 9C alkane heptane, nonane
    2C, 4C alkyne ethyne, butyne
    1C, 3C alkene does not exist, propene

    Mnemonic for first four prefixes


    First four prefixes

    MethEthPropBut-

    Monkeys
    Eat
    Peeled
    Bananas

    Other prefixes

    Decade
    Decimal
    Decathalon

    Pent Oct Dec Hex-, Hept-, Non-

    Numbering carbons
    Q- draw pentene
    A- Wheres the bond?
    We number C atoms

    H3C
    5
    1

    1-pentene

    4
    2

    2
    4

    1
    5

    Thus, naming compounds with multiple bonds is more


    complex than previously indicated
    Only if 2+ possibilities exist, are #s needed
    Always give double bond the lowest number
    Q - Name these

    2-butene
    H3C

    H3C

    C
    H

    H
    C

    C2H4
    CH3
    Ethene
    CH3 3-nonyne

    Multiple multiple bonds


    H3C

    CH3 2,3-heptadiene

    H3C

    2,4,6-nonatriyne

    CH2
    CH3

    Give 1st bond (1st point of difference) lowest #


    include di, tri, tetra, penta, etc. before ene/yne
    Comma between #s, hyphen between #-letter
    You do not need to know ene + yne

    H
    H

    H
    C

    HC

    2-butyne
    H

    H2C

    CH2

    CH

    1,2,4-pentatriene
    CH3CH2CH2CH=C=CH2 1,2-hexadiene
    H

    Cyclic structures

    H
    H

    H
    H

    C
    C

    H
    Cyclic structures are circular
    C C
    Have cyclo in name
    H
    H
    H
    H
    Benzene is not a cyclic structure
    cyclopentane
    Q- Draw these (note: carbons in a double bond
    should be consecutive- 1 and 2, 5 and 6, etc.):
    cyclobutene 1,3-cyclopentadiene cyclopropane
    H

    H2C

    CH2

    HC

    CH

    H
    C

    C
    C
    H

    C
    C
    H

    CH2

    H2C

    CH2

    Naming side chains

    CH3

    H3C
    CH3
    Names are made up
    of: side chains, root
    2,3-dimethylpentane
    CH3
    Root is the longest possible HC chain
    Must contain multiple bonds if present
    Add -yl to get name of side chain
    H3C
    CH3
    Common side chains include:
    CH
    CH3- methyl
    CH3CH2- ethyl
    *
    CH3CH2CH2- propyl (CH3)2CH- isopropyl
    iso (branched) is not an IUPAC convention
    Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)

    Naming side chains


    Example: use the rules on the bottom of
    handout to name the following structure
    CH2
    CH3 CH2 C

    CH2 CH3
    CH2 C

    CH3

    CH3

    Rule 1: choose the correct ending


    ene

    Naming side chains


    CH2
    CH3 CH2 C

    CH2 CH3
    CH2 C

    CH3

    CH3

    Rule 2: longest carbon chain


    ene

    Naming side chains


    CH2
    CH3 CH2 C

    CH2 CH3
    CH2 C

    CH3

    CH3

    Rule 3: attach prefix (according to # of C)


    1-hexene
    ene

    Naming side chains


    CH2
    CH3 CH2 C

    CH2 CH3
    CH2 C

    CH3

    CH3

    Rule 4: Assign numbers to each carbon


    1-hexene

    Naming side chains


    CH2

    CH2 CH3

    CH3 CH2 C

    CH2 C
    3

    CH3

    CH3

    Rule 4: Assign numbers to each carbon


    1-hexene

    Naming side chains


    CH2

    ethyl

    CH2 CH3

    CH3 CH2 C

    CH2 C
    3

    CH3

    CH3

    methyl

    methyl

    Rule 5: Determine name for side chains


    1-hexene

    Naming side chains


    CH2

    ethyl

    CH2 CH3

    CH3 CH2 C

    CH2 C
    3

    CH3

    CH3

    methyl

    methyl

    Rule 6: attach name of branches


    2-ethyl-4-methyl-4-methyl-1-hexene
    1-hexene

    Naming side chains


    CH2

    ethyl

    CH2 CH3

    CH3 CH2 C

    CH2 C
    3

    CH3

    CH3

    methyl

    methyl

    Rule 7: list alphabetically


    2-ethyl-4-methyl-4-methyl-1-hexene
    1-hexene

    Naming side chains


    CH2

    ethyl

    CH2 CH3

    CH3 CH2 C

    CH2 C
    3

    CH3

    CH3

    methyl

    methyl

    Rule 8,9: group similar branches


    2-ethyl-4-methyl-4-methyl-1-hexene
    1-hexene

    Naming side chains


    CH2

    ethyl

    CH2 CH3

    CH3 CH2 C

    CH2 C
    3

    CH3

    CH3

    methyl

    methyl

    Rule 8,9: group similar branches


    2-ethyl-4,4-dimethyl-1-hexene

    Naming side chains


    Try PE 1 on pg. 1019 (answer to a is wrong)
    H3C

    H3C

    CH2
    CH CH3

    H2C

    CH2

    CH CH CH2 CH3
    H3C

    CH3

    3-methylhexane

    CH2 CH2 CH3

    CH
    CH3

    4-ethyl-2,3-dimethylheptane

    CH3

    CH3

    CH3

    CH3 CH2 CH CH CH CH2 CH CH3


    CH2 CH3

    5-ethyl-2,4,6-trimethyloctane

    Naming side chains


    Name the structures below
    CH3
    H3C

    CH

    CH2
    CH
    CH3

    H2C

    H3C

    H3C

    3-ethyl-2-methylpentane

    CH3

    CH3

    3-ethyl-1,5,5trimethylcyclohexene
    CH3

    More practice
    Br

    4-bromo-7-methyl-2-nonene

    Br

    2,5-dibromo-6-chloro-1,3-cycloheptadiene

    Br
    Cl

    CH3
    H3C

    C
    CH3

    CH2 C
    F

    CH CH CH CH3

    5-fluoro-7,7-dimethyl-2,4-octadiene

    Pg. 1049 # 24.5, 24.6, 24.7, 24.14, 24.15


    Ignore 24.15 e)

    Pg. 1049
    24.5 - Recall, the exceptions to organic
    compounds are oxides of carbon, carbonates,
    bicarbonates, cyanides.
    b) is an oxide, d) bicarbonate, e) carbonate
    24.6 - This is a straight chain molecule as all
    carbons are consecutive.
    24.7 - none are possible: a) one too few Hs
    (should be CH3CH2CH3), b) one H too many
    (should be CH2=CHCH2CH3), c) one H too
    many (should be CH3CH=CHCH2CH3).

    24.15
    2,2-dimethyloctane

    1,3-dimethylcyclopentane
    1,1-diethylcyclohexane

    6-ethyl-5-isopropyl-7-methyl-1-octene

    H3C

    Aromatic nomenclature
    There are 2 naming methods
    1) Numbering carbons
    2) ortho, meta, para (stomp)

    H3C

    1,2-dimethylbenzene
    orthodimethylbenzene
    CH3

    ST Ortho
    H3C

    Meta
    Para

    Benzene is very stable


    (does not generally
    undergo addition)

    H3C

    1,3-dimethylbenzene
    metadimethylbenzene
    H3C

    CH3

    1,4-dimethylbenzene
    paradimethylbenzene

    More practice
    Build a molecule that can be named
    according to the rules that we have talked
    about. Make it challenging.
    Place your model at a vacant lab station.
    On a scrap piece of paper write the following:
    1) your station number, 2) the structure of
    your molecule, 3) the name of the structure.
    Give this to your teacher.
    Rotate through the stations, drawing the
    structures and determining their names. At
    the end of the class students will reveal the
    answer with an explanation.

    For more lessons, visit


    www.chalkbored.com

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